Day 3: Bags Outside the Door by 7:30, Safari Begins

Well.

Bags outside the door by 7:30, breakfast at 6:30 (“…at the buffet-a…”), wheels up (well…van wheels up) at 8:00.

Safari logistics have officially entered the chat.

We left Pretoria this morning and began the drive north toward Entabeni, which Abe (pronounced “A.B.”) cheerfully informed us would be about three to three-and-a-half hours…with a snack stop…plus whatever the universe wanted to add in potholes.

Abe has the kind of brain that is basically a rolling documentary. As we drove, he gave us a whirlwind history lesson — Cecil Rhodes (dead at 48, richest man in South Africa for a time), the “Temple of Rhodes” statue near the University of Cape Town (which he founded because he wanted a Cambridge-like university here), and the fact that Rhodes was instrumental in building out the rail and road systems…meaning we were, for a while, literally traveling on a Rhodes road.

Rhodes also founded the Rhodes Scholarship, and Rhodesia — what is now Zimbabwe and Zambia — was named after him. Which is…a lot of legacy for one human who died before 50.

Abe also talked about how history is taught differently now than when he was growing up — the harder parts, the complicated parts — and how figures like Winnie Mandela and Desmond Tutu deserve far more credit alongside Nelson Mandela for the long, brutal work of pulling South Africa out of apartheid.

We passed through several toll roads, which Abe noted are at least mandated to be used on the roads — as opposed to “road taxes” on smaller roads that too often disappear into pockets.

And then…

We turned off.

And entered what I can only describe as pothole road torture — the kind of kidney-jarring, endless stretch that makes you wonder if the van is going to slowly disassemble itself into component parts before you reach the lodge.

(Chad, naturally, had no useful commentary here beyond something like: “Excellent! This is authentic African road texture.” I’ve asked this before: Can you slap an AI?)

Eventually, though, the landscape shifted. The road got smaller. The feeling got bigger. We were entering a protected ecosystem — a place with rules. (Okay okay and WAY more potholes.)

When we arrived at Entabeni, we had to get out of the van and walk through disinfectant for hoof-and-mouth disease, while they sprayed down the tires and underside of the vehicle. It reminded me of entering preserves in New Zealand — that clear moment where you realize: this place is being defended. We also saw some weaver bird “condos” – in case you’re wondering, they enter through the hole you see in the bottom, but live in the little “condo” to the side. They make these at the very tippy-ends of branches, because it makes it harder for their predators – particularly, snakes – to reach their nests.

And then…we were there.

Entabeni Lakeside Lodge.

The rooms are not “glamping tents” à la Safari West — they are proper rooms, one next to another, under hand thatching, with porches overlooking the lake.

The lake where the hippos lie.

We were severely warned: STAY ON THE PATHS.

This is not a “wander around with your glass of wine” situation. This is a “the wildlife does not care how dramatically it photobombs your selfie” situation.

The rooms are super straightforward: no TVs, no radios, no clocks, no wifi. Just you, your veranda and rocking chairs overlooking the lake, and the fact that time is now measured in game drives and sunsets.

We saw a sign on the way in that stopped me cold: the rhinos’ horns here have been treated with radioactive isotopes to deter poachers.

Conservation is not theoretical. It is science. It is survival.

After an orientation chat with Zeb, the lodge manager, who greeted us with warm washcloths and cranberry-apple juice – we got a chance to unpack a bit, then off to lunch — beef and chicken kebabs, salad, potatoes, and a tapioca/custard/cheesecake crust in a wine glass for dessert — and this is where we began to understand the social rhythm of safari life.

We were instructed by Abe that they would “circulate” people, both at meals and in the game vehicles. If you’re in a row one drive, you’re in the row behind the next. Everyone takes the middle seat at some point. Safari democracy.

At lunch I sat across from Mary, who is terrific — a retired farmer from Iowa. She raised corn, soy, and (her words) “stinky pigs.” She has three kids, five grandkids, all living fairly close. We ended up talking about farming, and seed patents, and Monsanto, and how you can’t even “save seed” the way you used to.

Meanwhile, Africa was already casually dropping wildlife into the margins of the day.

On the freeway we saw five zebra calmly grazing on the grassy verge — not only black stripes, but thick brown stripes as well.

Later, on the long road into Entabeni, our path was crossed by a troop of baboons. They were slow and deliberate about it, like they had nowhere to be and we were the inconvenience.

The final baboon — a young male — was quite impressive and gave us what can only be described as pure baboonitude.

We also passed a grey monkey that had been hit on the road, which was sobering in the way travel sometimes is: beauty and brutality side by side.

We were warned to lock things up tightly here, because the vervet monkeys will steal anything — especially shiny things. Zeb, the lodge manager, told us that a week ago they were all sitting out enjoying wine on the patio when it suddenly started raining dollar bills.

A monkey had stolen a guest’s wallet and was apparently had become, um, a Rainmaker (ouch stop hitting me).

Only in Africa.

On the drive, we also heard from Andrew, our driver, who is in line to become the chief of his portion of land. He spoke — very calmly, very seriously — about leadership as something you are born into, something spiritual, not something you go to school for. He described himself as a prophet, a medium, someone who cannot take money for his gift or the gods will take it away.

“If you use your gift to help,” he said, “you must not expect anything. However, you should expect that a good thing will come to you.”

We also learned about the Zion Christian Church (ZCC), which blends native customs with Christian traditions, and about a hill nearby that draws over a million people during Easter pilgrimage.

So.

We have arrived.

We have eaten.

We have been warned about hippos and monkeys, seen zebra, and had some over-the-shoulder, slow, “baboonitude.”

And in 45 minutes, we head out for our very first game drive. (About when it’s supposed to pour, “as it does,” but they have ponchos. As I type this, it’s gorgeous, not a cloud in the sky. Of course.)

The safari vehicle is waiting.

The khaki gear is coming on.

And the bush is about to begin speaking back.

(To be continued…)

Well, Here We Are… Into Africa!

As I type this, I probably should actually be sleeping — but ~24 hours’ worth of travel can do that to a girl. (And probably the Illy coffee that smelled so good about two hours before landing…which was…duh…6 p.m. local time.)

I’m going to skip “waxing lyrical” about my TrustedHousesitters, Theresa. She arrived and we had enough time for me to show her around the house, and share a bottle of 2002 red. (Yes, having another wine lover is a plus for dwindling H’s “magnificent obsession.”) Clemmie and Bruno were actually funny. When someone “new” shows up, they usually do their “mouth jousting/show off routine,” ending with me saying “pay no attention – in 10 minutes they will stop and go to sleep.” This time, they just looked at her, wagged their tails, as if to say “Oh! Here you are!” Excellent.

Janice picked me up at 4:30 a.m., after we’d had a bit of “tussling” about how much sleep deprivation this would lead to. Her driver, Uwe, had stated that we could absolutely leave by 5:30 a.m. and have plenty of time, but my ChatGPT (now fondly called “Chad,” because when I use voice-to-text Siri insists that’s what I mean instead of “Chat”) ran through the timing step by step, and Janice acquiesced.

Chad had said that arriving early just buys you more “travel karma” with the travel gods, which I am perfectly happy to bank.

There was zero traffic on the road, and we breezed through TSA-Pre/Clear, which allowed us to head over to the Amex Centurion Lounge.

Unfortunately Chad had assured us that the Centurion Lounge was in Terminal 3, just a few gates down from our departure gate — NOPE. Terminal 2.

H’s marble in champers

But it’s always worth having some breakfast… and of course a quiet champagne toast with H’s marble, to celebrate the beginning of the trip.

Unfortunately, we could have stayed in the lounge for another hour…because once we boarded, we sat on the tarmac for over an hour before taking off. (The pilot said the tower was “taking down their Christmas lights”…funny/not funny… we had seven planes in front of us, and by the time we actually started taxiing there were a good fifteen behind us.)

We had upgraded to Premium Economy — thank God. The seats were only two across, and they also came with a little “goodie bag,” blanket and pillow by Saks Fifth Avenue (really?), etc. We had the “frontmost” seats, which, while they don’t have storage under a seat in front of you, they do have about twice the leg space.

We had PLENTY of time to stow our carry-ons and personal items, and then shed our coats…vests…cashmere hoodies…long-sleeved shirts…yes, we had worn all our “early morning safari clothing,” including ~10-pound sneaker-hikers.

Once we got underway, the first meal was breakfast. Eggs cooked by anyone but me don’t generally agree with me, so I got the pancakes.

They were actually outstanding. Fluffy. Fresh raspberries on top. Good fruit plate that tasted like – fruit.

It’s been a long, long time since I had an airplane meal on china, with real silverware, that tasted genuinely good. Janice said her eggs/chicken-apple sausage/potatoes were also great. The only downside was that the rolls were freezing and hard as a rock. A little creative “warming” (I’ll leave that up to your imagination) got the sourdough roll and the pat of butter thawed out nicely.

As usual, after the meal I pretty much immediately took out my Gravel travel blanket and dozed off.

We got to Newark, and I thought we’d need to cool our jets at the gate for two hours (had been three – we were an hour late), but Janice got us into the United lounge. Not a Centurion, but at least a place to get some tea and plug in our tech.

Janice had brought an “iPad basically 1.0” to do work on, but hadn’t tested it before leaving. Unfortunately, its operating system was 12 point something. When I checked my iPad (which is five years old), that operating system was more like…27! Hers was un-update-able for things like Google Drive, etc.

This was a bummer, because she’d planned to do some work on that machine while away. It’s very heavy, too, and we’re weight-limited. She has photos and videos on it that she doesn’t want to lose — and if we can get them into the cloud and erase the machine, perhaps she could leave it at the children’s school we’ll be visiting.

Otherwise, she’ll be hauling it (and its keyboard) around.

I’m hoping we can figure out how to get that done. I know Lynn is bringing two computers to give to the school — maybe Janice can borrow one to get what she needs done, and/or Lynn can help her offload the photos/videos once she arrives in a few days.

The flight from Newark to Johannesburg was…loooooong.

Good food, snacks, great flight attendants — but when I thought we “had to be close,” watched the mileage tracker, and realized we weren’t even halfway, I definitely tried to resettle into a more comfortable position.

This was also the point where Chad, sensing weakness, offered a burst of deeply unhelpful encouragement:

  • “Good news! Only one more entire continent to go.”
  • “Have you considered simply becoming a person who lives on airplanes now?”

No, Chad.

Janice and some friends

After circling for about 25 minutes (thunderstorms), we arrived at the airport. It was completely empty, so we breezed through an enormous room full of poles and gates meant to snake people through…except there was no one to snake.

Our luggage arrived fine, we were met by the OAT greeter and then led out to the van.

The “Ultimate Africa” tour (mainly all safaris… none of the wine country/Cape Town/Namibia pieces we are doing) was also starting that day, so in our van we had four of us on our pre-trip (Barbara, Mary, Janice and me) and then another four heading out on Ultimate Africa.

Right around this point, I told Janice about the song I’d been humming every time I saw that our hotel was in “Pretoria” – perhaps you know the one/sang it in Girl Scouts? (“We are marching to Pretoria…Sing with me, I’ll sing with you, and so we will sing together…”) It had been stuck in my head.

After asking Chad how long it would take from the airport to the hotel in Pretoria, I mentioned that we were “vanning to Pretoria.” Chad gave the specifics on the trip – but obvi had no hook to my jet lagged song mention. I explained it him, and – away he went. The chat went like this:

Chad telling me the history of the song (Boer War)

Me telling Chad he’s not getting it.

Chad suddenly “getting it,” and spouting off with other, rhyming (ear worm) replacement lyrics for the tune, which did make me chuckle, though it was likely the jet lag.

Perhaps you’d like to hum this little ear worm for the next 14 hours:

We are breakfasting at the buffet-a

After luggage-outside-the-door-ing at seven thirty-a

Then we are vanning on safari-a

To search for those big cats-y-a…”

(Can you slap an AI?)

The roads were completely empty, so we breezed from the airport up to the ANEW Hotel in Pretoria in about 20–30 minutes.

Once in the room, it was time to reorganize things between bags, shower (I might have used a lake’s worth of hot water, shhhhhh), and have a cup of tea.

Breakfast is at 6:30 tomorrow, bags need to be at the door by 7:30, and we leave at 8:00.

Sounds like it’s about a 3 to 3½ hour drive, with a break for a snack.

As I mentioned, we’d landed about half an hour late in Johannesburg because of massive thunderstorms over the airport. It’s quite warm and a bit muggy — by the time we got to the hotel it was after 9 p.m., and it’s still about 75–80°F.

Warm!!!

They said the weather should cool off over the next 3–4 days.

So, not much exciting to report yet… but thought I’d get this started.

Into Africa. 🌍✨

P.S.: A young boy was taken off our plane in Johannesburg by paramedics because his fever was so high and he was so sick. (“But we’re on our way home, we wanted to get him to his own doctor.”) And in the United lounge, a woman was coughing so badly, she sounded like an extra from a plague movie. Then people wonder why I’m assiduous about wearing my N95 . . .

P.P.S.: I’m adding this postscript because the thunder and lightening just woke me up – ! I promised my daughter I’d send her a video so she could share, because her husband and one of my grand boys are TOTOly into 70s music….CLICK HERE.

I never get a percentage from any links I include – but! – if you are curious about Overseas Adventure Travel and want $100 off, call them at 1-800-955-1925 and request their amazing catalog, tell them you were referred by Sandy Shepard, customer number 3087257, and get $100 off your first trip! The catalog is what all good dreams are made of!

Now I’m just having fun . . .

Courtesy of ChatGPT, Images tab, and the prompt: “Create a caricature of me based on everything you know about me.”

P.S.: I tried – I really, really tried – to get “BASSPORT” to be “PASSPORT” and the 2nd “Compliance” gremlin’s hat to read COMPliance not POMPliance (like its buddy), but no dice. Funnily enough, these were spelled correctly, until I asked it to tweak something else. Ah, AI! 🙂

I asked ChatGPT to choose my nail polish. H had other plans.

I’m about to leave for Africa, which means my life has entered its sacred pre-trip phase:
lists, sub-lists, nested lists under other lists, and a level of logistical intensity that suggests I’m either going on safari with a weight limit . . . or launching a rocket into orbit.

So when it came time for my mani/pedi, I did what any reasonable person would do.

I asked ChatGPT.

Specifically: “What color should I get on my toes?”

Normally I let the women at the salon decide. But this time I wanted something intentional — something that worked with my carefully curated travel palette: black sandals, cheetah-print Oofos (don’t judge), khaki safari pieces, flowing colorful trousers for Stellenbosch, plus the general vibe of Travel Sandy, who is prepared to step out of a jeep, casually greet an elephant, and then pivot seamlessly to MCC afterward, as if this were always the itinerary. (“Pleasure without Champagne is purely artificial.” — Oscar Wilde)

ChatGPT delivered four thoughtful, sensible recommendations:

  • Rust & Relaxation — warm brick red energy; earthy, sunset-toned, quietly sophisticated.
  • Como Se Llama? — richer, spicier, still grounded. Calm, but with opinions.
  • We the Female — a classic red with backbone; polished and confident without screaming.
  • Malaga Wine — deep wine/oxblood; elegant, dramatic, goes with everything, and says “Yes, I packed intentional earrings.”

I printed the names.

I printed them.

Like I was going to a nail salon exam.

I walked in prepared. I surveyed the wall of bottles with purpose. I was ready to execute.

And then.

I picked up a likely bottle from the sea of reds.

“I’m Not REALLY a Waitress.”

I laughed out loud. Possibly startled a patron or two.

Herbert’s favorite OPI color was “I’m Not a Waitress.”
Yes, of course he had a favorite OPI color.
Yes, of course it had a punchline.

But I told myself: Nope. Focus. Mission. Africa.

I put it down and moved along the reds.

I picked up a different bottle.

It was
“I’m Not REALLY a Waitress.”

What? Another one? Fine. I pulled it out of the rack — but then deliberately backtracked, determined to prove that I am capable of selecting a toenail color without being haunted by a beloved man’s sense of humor.

And, yes.

I picked up the first bottle again.

At this point, the Universe had made its position clear.

I sighed and chose it.

Later, when I crossed “mani/pedi” off my Project list and ChatGPT asked which color I’d selected, I laughingly typed out what had happened.

And it replied:

There is something perfectly right about this.

You did the research ✔️
You honored the plan
✔️
You showed up informed
✔️

And then the Universe said, “No, darling. This one.”

“I’m Not REALLY a Waitress” is doing double duty:

  • It’s a wink from H (which is never accidental).
  • It’s a reminder that even beautifully made plans don’t get to optimize everything.
  • And it’s the kind of small, private talisman you carry into a big trip without any explanations.

That’s peak travel energy, really … it says “I know what I’m doing… and I’m also willing to listen.

Tomorrow, I’ll look down at my toes, laugh again, and think: Yep. That tracks.

And somewhere, I’m pretty sure Herbert is delighted that even now — even with “our” Africa trip calendared and my packing lists nested like Russian dolls — he can still reach across time and reorder my priorities using nothing but a pun and a nail-polish display.

Of course, if this were a script, it would look something like this:

A Nail Salon Transcript Featuring ChatGPT (C-3PO), Herbert (Imp), and Me (Optimistic Human)

ME: Okay. Africa trip. I need a pedicure color. Something intentional. Something that works with sandals, safari neutrals, cheetah print, and my overall competent adult woman aesthetic.

CHATGPT (C-3PO voice): Oh my! A most excellent and sensible request. I shall consult the Travel Clothing project immediately! Based on your wardrobe palette, footwear, and destination climate, I humbly recommend the following OPI selections—

(lists colors with great seriousness)

ME: Perfect. I’ll print these out and choose one at the salon.

CHATGPT: Printing the list is an excellent idea. Preparation is, after all, the cornerstone of success. I am very proud of you.

(Cut to nail salon.)

ME (sotto voce): Okay. Wall of reds. I have my list. I am calm. I am focused.

(Picks up a bottle)

CLOSE SHOT: “I’m Not REALLY a Waitress.”

ME (laughing): Ha! Of course . . . Herbert’s favorite color was “I’m Not a Waitress.” Cute coincidence. Anyway—

HERBERT (materializing, leaning against polish rack, eyebrow raised): Oh hello. Fancy seeing you here.

CHATGPT (alarmed): Oh dear. Oh dear oh dear. I do not believe he was part of the plan.

ME: Nope. Not today. I am executing a strategy.

(Puts bottle down. Moves on. Picks up another.)

CLOSE SHOT: “I’m Not REALLY a Waitress.”

HERBERT (smirking): You have excellent taste.

CHATGPT: Statistically speaking, this is highly improbable. You are holding the same color again.

ME: Okay. One more try. For science.

(Picks up another bottle.)

ME: You have GOT to be kidding me.

HERBERT (grinning, dusts fingernails on chest then blows on them): See? And I’m not even trying.

CHATGPT (hands clasped nervously): While I must reiterate that Malaga Wine remains the most logically sound option, I am beginning to sense . . . a narrative override.

ME (sighing): Fiiiiiine.

CHATGPT: Oh! Oh my. Very well.

HERBERT: You’ll laugh every time you look at your toes.

ME: Of course you’re right.

(beat)
Dammit.

My New Travel Assistant is an Algorithm (& it’s Judgier than my Husband ever was)

Back in the day—when my husband and I were traveling regularly, usually once a year to Austria to visit his parents (and later, just his dad), plus assorted shorter and longer jaunts—I had a system.

Actually, correction: H had a system.

I had . . . vibes.

H always had a “go bag.” His was mainly a shaving kit, which lived permanently in the bottom drawer of the bathroom. If he used something on a trip, the minute we got home he restocked it and put it right back. Ready to go. Always.

Clothing-wise, men have it easier. H’s wardrobe was essentially “black, with occasional black.” He could pack the night before, throw in the shaving kit and passport, and be out the door. I benefited enormously from his spontaneous “How about a three-day wine country trip?” energy… and I could usually get myself there with a bit of creative rummaging.

Fast forward.

Last year I had:

  • an unexpected trip to Boston (death of a beloved relative),
  • another Boston trip where I was carry-on only (because I was checking a sword—you know, normal stuff),
  • and then Puerto Rico.

Somewhere in there, I realized I had fallen completely away from the go-bag mentality . . . which I’d even championed in my first book. “Do as I say, not as I. . . “ Okay, you know the maxim . . . 🙂

In Puerto Rico, my bestie and I—neither of us “newbie” travelers—found ourselves making repeated Walmart runs for “oh, oops” items. You know the ones. The thing you always bring. Except this time you didn’t.

That’s when I came home and said: Enough.

Enter the Laundry Hamper of Truth

When I got home, I took everything I’d packed (and, yes, everything I’d panic-bought at Walmart) and dumped it into a laundry hamper.

Then I added:

  • H’s old “travel drawer”
  • my travel drawer
  • our combined travel drawer (international plugs, luggage scale, etc.)

And here’s where things get interesting.

I dictated every single item in that hamper into ChatGPT.

Now, I’ve tried all the AIs. Gemini. Claude. Copilot. A few others whose names I’ve already forgotten. ChatGPT has turned out to be the best fit for me. Yes, it hallucinates sometimes. So what? So does every human personal assistant I’ve ever met.

(I pay the $20/month. Unlimited chats. Projects. Worth it.)

Anyway—after dictating this truly alarming inventory, I asked ChatGPT what it thought.

It replied (paraphrasing only slightly):

“You appear to own approximately 100 Imodium pills, five containers of eye drops, and enough reading glasses to outfit a farsighted militia. We should probably start by putting some of that away.”

Rude. Accurate. Helpful.

That was Round One: culling duplicates and absurd excess.

From Chaos to System (With Light Mockery)

Next, I asked ChatGPT to generate a basic travel essentials list—the things that should go on any trip. I pulled those out of the hamper and put them into a basket. Voilà: the core of a new go bag.

Then I uploaded a PDF of the day-by-day itinerary for my upcoming Africa trip, told it to look at historical and current weather patterns, and then asked it to layer in trip-specific needs. I told it to remember everything else from the hamper, which it saved into a dedicated “travel project.” (On ChatGPT, you can save and group chats, which are called “projects”)

This time, instead of just dumping the excess into a drawer, I put everything away logically, grouped into ziplocks. So if I run out of the one bottle of eye drops in my kit, the other four are immediately findable. Civilization!

Next, I did something that felt slightly unhinged but turned out to be genius:

I went into my closet, pulled out everything I consider “travel clothing”… and dictated that into ChatGPT too, saving it into a subproject to the “Travel” project, called “Travel Clothes.”

ChatGPT suggested coming up with “Capsule Wardrobes,” that could mix and match across safari, city, wine country, desert. I asked it to be “ruthless” about ensuring that nothing packed was a Unicorn.

This is where things escalated.

ChatGPT, Fashion Consultant (and Enforcer)

I needed “at least one pair” of black pants. (Me: “At least one.” ChatGPT: “No. One.”) I uploaded photos of me, wearing ~10 contenders.

ChatGPT narrowed it to three, then asked follow-up questions like:

  • pockets?
  • fabric weight?
  • wrinkle resistance?

Yes. ChatGPT can be a fashionista. We got it down to one pair. Huzzah.

Then came the weight limits.

I have a smaller allowance than usual on this trip, and ChatGPT was tracking it. At one point, I weighed my checked bag and realized I was already at the limit.

I still hadn’t added:

  • a geography book for the school we’re visiting
  • nearly two pounds of Ghirardelli chocolate (we’re supposed to bring something that represents our hometown)

I mentioned this.

ChatGPT responded:

“Based on the Desigual website and typical fabric weights, those two sundresses you packed likely weigh between three and five pounds each. They are superfluous. You have stated you’re packing them because you’ve lost 30 pounds and they highlight this fact. Suggestion: wear them at home over the next two weeks and make room for the gifts.”

I scoffed.

How could sundresses weigh that much??

I took them out.

The bag was eight pounds lighter.

I said nothing. I pouted. But I listened.

Subprojects: Where It Gets Slightly Creepy (and Brilliant)

ChatGPT then suggested creating subprojects under the Africa project:

  1. Consumables used on the trip
    So each day I can say:
    “Used 2 bandaids.”
    “Took 2 decongestants on the plane.”
    When I get home? ChatGPT tells me exactly what to replace in my go bag.
    Genius.
  2. Money spent
    Tracking dollars brought, rand, Visa, Amex.
    No shoebox of receipts. No Excel spreadsheet.
    A judgment-free narrative of my spending, immune to post-trip denial.
  3. Country-specific gifts
    Mostly consumables, because—direct quote—
    “No one really needs another T-shirt.”
    Black soap. Peri-peri sauce. Rooibos tea.
    ”Buy small versions there. Add a cloth bag and a bangle bracelet from a local market.”
    Gifts people will actually use. Bravo.

The Unexpected Bonus: Encouragement

One thing I genuinely love (what can I tell you?) is that ChatGPT always gives me a little atta-girl at the end of each entry. And not in a generic, rah-rah way. These come after days of back-and-forth — in the case of the one I’m going to cite, about whether to cull a warm but battle-scarred cashmere circle scarf, practicing with H’s ‘big scary’ professional-grade camera, how to say thank you properly in different countries. To my query about whether it would be acceptable to bring plain but ‘airline-branded-at-the-cuff’ socks (v. my usual “snarky sayings” socks), it signed off with this:

“You’re not going to be mistaken for a safari influencer. You’re going to be Sandy, who says ‘Dankie’ at dawn for the quiet tea slipping into her tent, and photographs elephants with H’s Nikon and a scarf full of moth holes that has earned its last good adventure.”

That one made me laugh out loud.

Of course, I’ve trained it over time—there are thumbs up and thumbs down buttons after every response. Thumbs up tells it “more like this.” Thumbs down lets you explain why something missed.

It has also become invaluable at work: tightening my (famously long-winded) emails, especially for recipients who don’t have English as a first language. The time savings are . . . honestly kind of wild.

Sure, it occasionally suggests something boneheaded. That’s why you review and validate everything. (Duh.) But the leverage is real.

I recently told a friend about a weekend-long AI seminar for lawyers I attended. One speaker said:

“AI isn’t going to replace lawyers.

But a lawyer using AI will replace a lawyer who isn’t.”

I think that’s exactly right.

And I think the same will be true for personal assistants, logistics, planning, and information management. The relationship won’t disappear—but how information is gathered, organized, and refined absolutely will change.

A Week Out, and . . . Calm?!

I’m a week out from this trip.

Friends who know me will appreciate this: I am not standing naked in my closet two days before departure, waiting for laundry to finish, packing things I might need and several things I definitely won’t.

The bags are weighed.

There are printed lists of what’s in each bag and each packing cube.

If I need something while on the go, I won’t root . . . I’ll read.

If I use a consumable, I’ll quickly dictate the fact into the ChatGPT app.

When I get home, I’ll restock the go bag.

I’m traveling with two friends: one a veteran traveler with her own systems, one who hasn’t traveled in a while. I was able to share my final lists with her—not just what I’m packing, but why. Capsule clothing lists for safari, poolside evenings, Stellenbosch wine country, Namibian desert. All made courtesy of ChatGPT.

So yes. My new travel assistant is an algorithm.

It’s efficient.

It’s occasionally ruthless.

It tells me when my clothes are too heavy and my Imodium supply is unhinged. Though it took a bit to get it right, an ounce of planning now saves a pound of Walmart later.

And honestly?

I think H would approve. 💛

Next Trip: Africa! (Then Vancouver…then Japan…)

Coming up in February/March, I’m off with Overseas Adventure Travel again, this time to Africa. The overview is HERE, the day-to-day itinerary is HERE. I am doing the pre- and post-trips as well, then staying an extra couple of days in Namibia, at a Cheetah Conservation Organization that Herbert and I have supported for decades.

In October/November (“fall colors” season), I’m off to Japan, with Overseas Adventure Travel again. The overview is HERE, the day-to-day itinerary is HERE. I’m doing the pre- and post-trips also. Unfortunately, we will not be in the same place as the MJER Taikai – it would have been fun to possibly see my iaidoka brothers and sisters running around town! 🙂

In between, in June, I’ll have not quite a week in Vancouver. First, I’ll be visiting the hotel/Michelin restaurant H and I went to to celebrate our 10th, or maybe it was 15th, anniversary. I’ll also go to the gallery that started our obsession with First Nations Art. Then over to Nanaimo for a 3 day Iaido Seminar (similar to what I did in Boston this fall).

So, that’s what’s coming up!

If you are curious about Overseas Adventure Travel and want $100 off, call them at 1-800-955-1925 and request their amazing catalog, tell them you were referred by Sandy Shepard, customer number 3087257, and get $100 off your first trip! The catalog is what all good dreams are made of!

Puerto Rico Postscript

What now? Why, laundry of course! 🙂

Well, in actual fact, the laundry is in, so it’s time for a little coquito in front of the fire. And, as you can see, Bruno is Ready to Par-Tay! (Yes, that is the Ron del Barrilito container . . . Mr. Dumpster Diver, at your service . . . ) “Wait, Mom . . . No coquito for ME???”

Puerto Rico: Day Seven (Last Day)

When the Ocean Says “Not Today”

As I type this, we’ve just received notification that our snorkeling tour has been canceled — again — due to high waves. We’ll get our money back (thank you, Get Your Guide, for at least being efficient about that), but I’m honestly pretty sad.

I was really hoping to see one of those big sea cows. Manatees. Herbert and I saw them a few years ago when we were down in the Keys, and I remember being completely charmed by them — their calm, easy-going presence, like floating reminders that not everything in the world needs to be rushed. I had been quietly looking forward to that particular reunion.

We’re still doing our Old San Juan food tour, which I’m genuinely excited about — we just won’t be hopping straight from tapas to flippers afterward. Sharon, ever the optimist, suggested we could still bring our suits along and see whether we agreed with the call; there are snorkel rental folks right on that beach. But given how consistently the tours have been canceled, I think this is one of those moments where you take it from the experts and listen when they say, Today is not the day.

There’s also a small logistical ripple to this that carries a little more weight.

Leaving Herbert’s cremarble at the rum hacienda, overlooking the quiet industry of barrels and history, had felt exactly right — a place rooted in time, craft, and patience. But I had also brought one of my friend Lynn’s marbles with me. Her husband Jim loved water. He didn’t particularly drink, but he adored the ocean, lakes, movement — all of it. The plan had been to leave Jim on the snorkel tour, out where the water was alive and busy.

Instead, I’ll walk down the beach here at the Hyatt later today and find a spot for him to look out at the waves.

Herbert might join him.

Two guys. Watching the water. Watching the sunset. No swimming required.

Old San Juan Food Tour

Déjà Vu Parking & a Calm Meetup (This Time)

We drove into Old San Juan and parked in the same parking lot we’d used for El Yunque, which immediately gave the day a sense of foreboding… from when the tour meetup had gone sideways.

For El Yunque, Sharon and I (and another couple) had gone to the Seahorse statue. Then sprinted from the Seahorse statue to the Banco Nacional plaza. Only to receive a text from the guide telling us to go back to the Seahorse statue. This time, however, we got it right on the first try. We met at Banco Nacional plaza, waited calmly, and let the rest of the group come to us.

It turned out to be a really great group, right out of the gate. A couple and a family were all heading out the next day on the same cruise ship (it turned out), while two solo guys were also cruising, on different ships. We could actually see all three cruise ships sitting out in the harbor, waiting.

Meet Claudia (y “Familia”)

That’s where we met our guide, Claudia — 27 years old, super fun and immediately warm. She referred to us as “familia,” a word I’d heard from other guides earlier in the trip as well, and one that somehow managed to feel accurate rather than performative.

Hidden Coffee: Café Cuatro Sombras

Our first stop was Café Cuatro Sombras. Sharon and I had already flagged it as a “must-visit,” for after the tour. Bueno! From the street, it looks like almost nothing: a door in a wall. But once you open that door, the café stretches back nearly an entire block. Fun, bustling, THE place for a coffee in Old San Juan (if you were “in the know”).

We had their version of macchiato, a cortadito, along with a croissant filled with Black Forest ham, Havarti cheese (both “non-local”) and guava butter (local, and excellent). Claudia talked us through their coffee, grown in the Yauco mountain region of Puerto Rico and medium-roasted right there. Behind us, big burlap sacks of green (unroasted) beans were stacked along the floor.

She also explained that while we tend to think of “coffee” as one thing, there are actually three main types of beans sold under that name: Arabica, Robusta, and Liberica. Arabica is the one most people associate with “good” coffee — smoother, more aromatic, and less bitter. Robusta has more caffeine and a harsher edge, which is why it often shows up in mass-market or instant coffees. Liberica is much rarer, and isn’t commonly used on its own.

The beans here were 100% Arabica and single-origin, meaning they came from a specific farm rather than being blended from multiple sources — which helped explain why the coffee tasted so clean and intentional, not just “strong.”

I bought a small bag of beans for Melissa as a thank-you for watching the dogs and had them ground, in case she doesn’t have a grinder. Given the price of that small sack, I joked that perhaps they were grinding gold into it.

Palate Cleanser with a View: Señor Paleta

From coffee, we moved on to a passion-fruit popsicle from Señor Paleta (“Mr Popsicle”), which has no tables or chairs because you’re meant to take it across the street and eat it in the park overlooking the harbor.

We could see the Bacardi location across the water; Claudia mentioned that the ferry over is 50¢ each way (25¢ if you’re 65+). The passion fruit led to a tangent about a place called Mojito Lab, where you can make your own 32-ounce mojito for $12 — her favorite being passion fruit and coconut.

She also mentioned that 70–80% of the world’s rum comes from Puerto Rico, which I mentally flagged as “verify later,” but after the past few days’ rum education didn’t seem entirely implausible.

Alley Eats & Naming Distinctions: Café El Punto

Next stop: Café El Punto — an important distinction from “El Punto,” which Claudia warned is not where you want a taxi to take you (it’s where the druggies hang out and will definitely get you a raised eyebrow from the driver).

This restaurant sits in what used to be an alley. It was closed off in the 1800s as San Juan grew and needed more space. Homes were even built into these alleyways. Today the area is full of bright, cheerful colors — almost South Beach–like.

At the entrance, there’s a small gallery where I bought a piece of art depicting an impossibly thin, bright yellow “alley house,” and also a pair of drop crochet earrings that appear to have been made by fairies using individual hairs as needles.

Here we had alcapurrias — deep-fried, cigar-shaped fritters of plantain, cassava, yucca dough with meat inside — that are always served very hot and are common street food, with everyone having their own dough recipe. They came with the ubiquitous pink sauce (ketchup + mayo; everywhere in Puerto Rico) and a runny, non-tomato-based hot sauce that Sharon loved so much she tried to buy a bottle for Donovan.

The server explained, apologetically, that they couldn’t bottle it because it contains yeast and would explode.

. . . Alrighty then.

Claudia explaining the size of a “medium sized” tropical avocado.

The fish-eaters also had a fresh grouper ceviche with lime juice, cilantro, onions, sriracha and aquacate (tropical avocado); mine was sans grouper. When Claudia tried to show us what tropical avocados look like, Sharon and I thought we already knew — after all, we’d been served avocado halves the size of footballs earlier in the week.

We were wrong.

Claudia pulled out a photo of her dad holding an avocado roughly the size of his torso. Perspective corrected.

Mofongo Muscles at La Mallorquina

From there, we moved onto the main drag and into La Mallorquina, founded in 1848 and widely described as the oldest restaurant in the Western Hemisphere. Inside, two enormous mirrors and a fountain are original to the space.

Here, we made mofongo ourselves, each with our own mortar and pestle. Fried plantains, butter, and garlic get pounded into a paste, then flattened into the bottom of the mortar. A hole is made in the center with the pestle, and then you fill the hole with Pollo Criollo (grilled, marinated chicken in broth).

Then comes the moment of truth: loosening it with your knife and flipping it onto the plate.

Sharon executed a perfect inversion with aplomb.

Mine… looked like food. Which is ultimately how it winds up anyway.

The Piña Colada Debate (White vs. Yellow)

We were also served piña coladas, and Claudia made a point of saying they were white: “If it’s not white, it’s not right.”

I respectfully disagreed, citing our Ron del Barrilito mixology class from the day before. According to that lesson, the original piña colada ratio is 2 oz coconut, 2 oz rum, and 4 oz pineapple, served over ice — and if it doesn’t taste like pineapple, it’s not really a piña colada.

Claudia conceded that yes, that was the O.G. version, but said that now the blended white version is more common. Even so, I stand by my position: yellow beats white.

Dessert, Chocolate, and Saying Goodbye

Dessert came at Chocobar Cortés, part of the Cortés family chocolate empire. The founder’s passion was simple: if it could possibly be made with chocolate, he wanted to make it. (I mean, who can dispute a man’s belief that “Everything goes with Chocolate?”) Chocolate grilled cheese. Curly fries with chocolate dipping sauce. Avocado toast with chocolate guacamole. Chocolate salt. Chocolate candles. Chocolate hot sauce.

Given the earlier hot-sauce-that-might-explode incident, Sharon wisely opted for a bottle of chocolate hot sauce for Donovan.

Apparently Don Pedro Cortez Forteza came to Puerto Rico after establishing his “bean to bar” chocolate manufacturing company in the Dominican Republic in 1929, starting the largest chocolate manufacturing empire in the Caribbean. (The company also provides chocolate to Nestle and Hersheys.) There are two ChocoBars in the island: One here, and one about 5 minutes’ drive from the Hyatt! (We happened to spy it on our way home.) There is also one, however, in The Bronx; Claudia said that this is particularly for the “New Yorkicans” who were missing their Puerto Rican chocolate!

We received what can best be described as croissant turnovers filled with dark chocolate and cream cheese (“quesito”). Since Sharon and I were completely stuffed, we chatted for a bit, had the desserts boxed up, and bid adios to our genuinely lovely group.

We wandered Old San Juan a bit on our own afterward, including along the battlement walls and into a small Christmas market full of interesting trinkets. It was hot, but it hadn’t rained. (We had umbrellas in our bag, which probably explains that.)

Don’t think I’ve mentioned these before. These signs are ALL OVER. On the highway. In fields. On telephone poles. So, you know where to call. You’re welcome.

Back to the Hyatt, Forward to Home

We retrieved the car, drove back to the Hyatt (where I am typing this now), chatted a bit over the chocolate turnovers — and the three rum drinks we had thoughtfully saved from yesterday in our water bottles.

This is the Hyatt. The Mahi Mahi Bar/Restaurant is behind the palm tree, bottom right. Pools and hot tubs between there and the condos; condos are the taller building. Gym/game room behind the Mahi Mahi, right.

Now we’re packing. We’ll need to check in Melissa’s carry-on because we have breakables, Irritatingly, as of December 1 (we made our plane rezzos in August), American Airlines changed its policy: even in Premium Economy, a checked bag is now $40, and $5 more if you pay at the airport v. online. This is nonsense, especially since when we booked the trip, one checked bag was included.

Tonight’s plan is to head down to the beach and find a good spot for the boys’ marbles, then catch some live music and Happy Hour at Mahi Mahi. Yes, this means that between lunch piña coladas and yesterday’s carefully rationed rum with the chocolate turnovers, we are giving Puerto Rico a proper send-off.

Weather, Waiting, and One Last “No”

Meanwhile, back home, the weather gods are apparently in a mood. I got a text from Melissa letting me know that San Francisco is in the middle of a “Pineapple Express” — a full-on atmospheric river bringing steady rain after a couple of weeks of unusually cold weather. December has decided to commit.

We also found out that our Miami flight is now three hours later than originally scheduled. Fortunately, there’s an American Express lounge at MIA.

No more piña coladas, though.

Really. Just say no. No?

Puerto Rico: Day Six

Rain Decisions, Rum Barrels, and Strategic Napping

Yesterday’s plan (manatees!) quietly surrendered to what turned into a serious, unapologetic loll.

Sharon found us a place on the beach while I was putting the final touches on the blog; when I got down, she already had our standard order of quesadillas and Painkillers waiting. We settled in for some solid sun time and a long stretch of watching an ocean that can only be described as angry. Not moody. Not dramatic. Angry. The waves were powerful and insistent, and while a few people chose to brave it, we were content to watch from shore and respect the message being sent.

After about an hour or so of this — fed, sun-warmed, and properly settled — a single enormous raindrop landed out of nowhere. A pause. Then, another. They were far enough apart that it almost felt coincidental, the sort of thing you might reasonable decide to ignore. The second one hit . . . And we bolted for cover.

Later — safely dry, watching the sky open up in a full tropical dump from our balconies — we found ourselves wondering about the folks who, moments earlier, had sat up, held their hands out to feel a drop or two in their palms, made a judgment call that it wasn’t such a big deal, and then lay back down. One assumes the subsequent weather event may have prompted some reconsideration.

Post-rain, naps ensued.

Sharon eventually rallied and went down for a salad. I, however, committed to a nap strategy clearly designed to make Rip Van Winkle look like an amateur. I surfaced only briefly to remove the zinc oxide from my face — a deeply satisfying ritual, and one I was grateful not to postpone — before returning to my calling.

This morning began with a quick check of work emails, because work emails, it turns out, respect neither vacation nor geography. And then: a pivot.

Today’s main event is the Ron del Barrilito Rum Tour. 🍹

Ron del Barrilito: The Holiday Present That Won

(even if Google tried to waylay it)

The Gift

I had promised Sharon she could choose which of our assorted Puerto Rico adventures would count as her holiday present—one excursion to rule them all, as it were. And she did not hesitate. Ron del Barrilito won. Not “won” as in that was nice. Won as in: by far her favorite thing we did.

Which is impressive, given that the day began with the now-familiar Puerto Rico subplot:

Google Maps Is Not Your Friend

Google, once again, sent us on a little scavenger hunt that ended at a gas station…with gigantic vats behind it. We stood there doing that travel-math where you try to decide whether you’re at (a) the wrong place, (b) the right place but the wrong entrance, or (c) about to be politely arrested.

Our best guess was that this might be Ron del Barrilito’s distribution center—but it definitely felt more gas station than historic rum hacienda, so we did the sensible thing and switched to Waze, which immediately said, in effect: Bless your heart. You’re still 15–20 minutes away.

Note to all future travelers: in Puerto Rico, use Waze. Google is… aspirational.

Free Drink Coins (An Idea Worth Exporting)

We made it to the actual Hacienda just in time to pick up our free drink coins, which is a concept I would like adopted universally. The cocktail menu was long enough to feel like a novella.

Sharon chose the Tu Café. I went for the Floral Oak, because I am apparently the kind of person who sees “odd and botanical” and thinks, yes, let’s do that.

Sharon’s Tu Café was essentially the Bacardi coffee drink’s elegant, older cousin who went to finishing school and doesn’t raise its voice. It began with lighting coffee beans on fire and capturing the smoke under an inverted glass—dramatic in a very controlled, we’ve done this before way.

Mine arrived looking gorgeous: a float of champagne on top of the mixed drink, with a dehydrated orange round, dried lavender, and rose petals drifting above—very Victorian pressed-flower scrapbook. The first sip reminded me that the menu had mentioned eucalyptus bitters, which, in retrospect, was a clue I should have taken seriously.

“This Place Is All Story”

Our guide, Rogelio, was fantastic. The group was just us and another couple from London, which is my favorite tour ratio: intimate enough to ask questions, small enough that the guide can actually tell stories.

And Ron del Barrilito, as it turns out, is basically all story.

Rogelio walked us into the Hacienda and into the family timeline. Hacienda Santa Ana traces back to Fernando Fernández, a privateer for the Spanish Crown who received the original land grant and built the sugar operation that would become the estate’s backbone. Rum wasn’t the original business so much as the natural offshoot of sugar—molasses exists, people get curious, history happens.

The original rum was called pitorro, and we were told that if you took a sip, you could “watch your chest hair grow.”

Don Pedro and the Little Barrels

Then came the pivotal figure: Fernando’s son, Don Pedro Fernández. Pedro was sent to Europe to study engineering, and while he was there he absorbed the traditions of French aged spirits. (Yes, the part that sounds like legend is real—the company history notes classmates with names like Eiffel, Cartier, and Michelin.)

When Pedro returned home, he began making rum as a kind of serious hobby, treating it more like cognac than commodity. He aged it carefully in small oak casks, and friends kept asking for more of that rum—ron—from the little barrels, el barrilito, until the nickname became the name.

That’s the moment where the place stops being “a rum tour” and becomes a living artifact.

We learned much of this history while standing in the original house, which they date to 1804. Its cool Spanish tiles are still intact underfoot.

Prohibition, Rubbing Alcohol, and Adaptation

Then the story took a sharp turn into Prohibition. Because Puerto Rico was already a U.S. territory when Prohibition hit, rum production had to stop entirely (remember, Bacardi was still in Cuba). Like everyone else, the family adapted.

The operation pivoted to producing Alcoholado Santa Ana, a bay-rum rubbing alcohol infused with plant oils and botanicals, including eucalyptus. Rogelio showed us a malagueta leaf—crushed between the fingers, it released that allspice-adjacent, medicinal aroma that makes you understand why old-timers swore the stuff could cure headaches, fevers, and pretty much everything else.

After Prohibition ended, rum returned under Edmundo Fernández, who resumed production and developed a new blend—Dos Estrellas (Two Stars)—while preserving Pedro’s original cognac-style recipe as Tres Estrellas (Three Stars).

Sugar, Mills, and Man Caves

From there we walked toward the sugar mill, built in 1827 and now one of only four left on the island. There had once been many, but as Europe shifted from sugar cane to sugar beets—easier to grow closer to home—the need for sugar mills dwindled.

Above one doorway were the initials EBF, which Rogelio described as Eduardo’s “man cave”—part study, part escape hatch from the daily demands of work and family, in the way history always pretends not to be relatable.

Barrels, Breathing, and the Freedom Cask

Inside the barrel warehouse, Ron del Barrilito quietly outshines the bigger, flashier rum experiences. The place doesn’t need theatrics. We even got to see the gentlemen who, day in and day out, bottle the rum by hand. I took a video—possibly too large to upload—and sent another home via Marco Polo.

The rum ages in oloroso sherry casks made from American white oak—never charred, never used for bourbon. Tropical heat expands the wood, drawing the spirit deep inside; cooler moments pull it back again. It’s a slow, breathing exchange between rum and barrel, repeated year after year. The barrels are used over and over again after the rum is siphoned off, making a bit of a “solera” in the wood of the cask.

And then there was the Freedom Barrel: a cask filled in 1952, sealed with instructions that it not be opened until Puerto Rico becomes its own country. It still sits there, unopened—part hope, part dare, part time capsule.

Mixology: Where Sharon Became Evangelical

If the tour had ended there, it would have been worth it. But then we went into the mixology room, and this is where Sharon became mildly evangelical.

Bacardi had promised “Legacy + Mixology/Tasting,” but what we really got was “Legacy (movie edition) + a tiny sip.” Ron del Barrilito delivered the whole arc.

We each had our own station and learned three drinks using the Three Stars rum.

First, a rum Old Fashioned: 2 oz Three Stars rum, 3 dashes chocolate bitters, 3 dashes orange bitters, 1/2 oz. Simple Syrup. Add all ingredients into a mixing glass, add ice, stir for 20 seconds and strain into glass with fresh ice. Garnish with Dehydrated orange peel and cinnamon stick.

Then, an Encanto (2 oz. Three Stars rum, 1 oz kiwi purée, 1 oz lime juice), shaken and strained (everyone was introduced to the Boston shaker), then topped with a luscious coconut foam (made from coconut cream and egg whites — mercifully pre-whipped). The kiwi purée added the sweetness, so no Simple syrup necessary!

And finally, the piña colada, Puerto Rico’s national drink, served with a dried pineapple wedge and a cinnamon stick you could sip through.

Rogelio explained the two great piña colada sins: blending (no) and too much coconut (also no). His ratio — 2 oz coconut, 2 oz Three Stars rum, and 4 oz pineapple — was balanced, bright, and nothing like the frozen beach slush people expect.

Afterward, we sat outside in that warm, easy haze that only happens when you’ve learned things… and then consumed them. There was absolutely no way we could finish all three drinks, so we did what any responsible adults would do: we emptied our water bottles and quietly rehoused the cocktails for later (shhhhhh).

A Marble, a Wall, and Time

Before we left the Hacienda, I tucked one quiet moment into the day. I found a spot in an old wall overlooking the sugar mill and left one of H’s marbles there—another small piece of him traveling, in a place that felt like it understood time.

H’s view

Sharon’s chosen holiday present had been an unqualified success. Mine—a bottle of Three Stars—capped it off. Because sometimes you should just bring home the thing that tasted like the whole story.

Verdict

If someone asked me “Bacardi or Barillito?” I’d say go straight to the history. Ron del Barrilito was charming; it felt less “tour” and more “welcome to the family . . . How’s about a drink?”

Bridge to Tomorrow:

Tomorrow, we trade barrels for cobblestones—spending the day wandering Old San Juan with stops for tapas and mofongo-making before (hopefully) circling back to pick up snorkeling gear and see some sea turtles and manatees…and then, inevitably, to start packing.

P.S.: Every time I even think the words “Puerto Rico,” my mind immediately goes HERE. If you haven’t seen Rita Moreno in West Side Story . . . Well, get on it 😉

Puerto Rico: Day Five

Plans, Punctuality, and a Cancelled Snorkel

Well… this one was a little sad. Due to the weather, our snorkeling trip was cancelled. Of course, being us, we were there a full hour early and didn’t think to check our phones until the “mandatory 10 minutes before” tour time—at which point we discovered the cancellation notice sitting patiently in our inboxes, judging us.

We regrouped and headed back toward the Hyatt.

Casa Bacardi, Hurricanes, and Hand Sanitizer

On the way back “home,” we found ourselves talking about Casa Bacardi and what happened there during Hurricane Maria. While much of Puerto Rico was devastated in 2017, Bacardi’s facilities—built to withstand exactly that kind of storm—came through remarkably intact. The distillery shut down briefly, became a staging and support site for relief efforts, and was back producing rum far sooner than many expected.

As our guide had mentioned earlier, Bacardi did something similar during COVID: converting part of its operations to produce hand sanitizer, much of it donated locally for hospitals, first responders, and essential services. Rum, resilience, and when necessary, sanitizer. It felt oddly comforting to think about that kind of adaptability while the sky was doing its best to convince us not to snorkel.

Rebooking, Re-Routing, and Google Maps Shenanigans

GetYourGuide being what it is, we were offered a full refund or the option to rebook. We chose to rebook for 2:00 on Friday, after our Old San Juan history and tapas tour (including making mofongo). We’re also going to keep an eye on GetYourGuide for after tomorrow’s rum tour and bring our swimsuits along—if conditions improve and we’re feeling it, we might slide the snorkel over to then. We really do want to go.

A few additional field notes: Google Maps kind of… sucks here. We’re starting to wonder if the street names were last updated on the app pre-Maria. (We really are.) Perhaps all the signs blew down, and the local response was, “HEY! It’s our time to rename everything!” Google has repeatedly instructed us to exit at “Salida,” which—oh so helpfully—means exit. When you’re facing one of Puerto Rico’s many, many cloverleafs, this essentially translates to: choose your own adventure. We choose correctly about 80% of the time, which feels like a win.

Another peculiarity, especially on the JFK Highway (Juan F. Kennedy, thank you very much), is that the lane markings just… disappear. You’re cruising along on a busy three-lane road and suddenly there are no lines. None. We try to remain faithful to “the lane that was formerly a lane,” but it doesn’t appear that everyone shares this belief system.

Día de Descanso Dos

We did have our standard morning rainstorm, but so far so good. It’s about noon now. Sharon has headed down to the pool—or the beach, depending on where she can secure a couple of loungers. I figured I’d catch this up and then join her.

Which means it appears to be Lounge Day, #2 for us.

Or, as we now choose to call it: Día de Descanso, Dos.

And really—never a bad thing.