Caribbean

March 2026

Dianne and I enjoyed a transatlantic repositioning cruise on the Explora 1 so much that I did a spreadsheet to figure out which of their upcoming cruises was the best bargain (in terms of dollars per day) so we could ruthlessly exploit all their amenities…again. The winner was an interesting but strange back-and-forth cruise across the Caribbean, starting in San Juan, messing around in some nearby islands, heading to Miami, heading back, messing around some more, then returning to San Juan. To be fair, it’s probably a couple of their cruises set back-to-back. We started out in San Juan and spent a couple of days there.

San Juan, Puerto Rico

So after landing in Puerto Rico, we finally figured out what was going on with Bad Bunny in the Super Bowl half time. As our president pointed out, “nobody understands a word this guy is saying”, but it turns out he was actually speaking another language, called Spanish, also spoken by 600M other people, and the primary language in Puerto Rico. Even though it’s a US territory. Go figure.

Villa Herencia

Dianne found this nice boutiquey hotel right in the middle of Old San Juan, a block from the cathedral. It’s on the “Cove of the Nuns” (Caleta de las Monjas) and is just a few doors from a convent (now also a hotel).

Street Scenes Around San Juan

We did a self-guided “scavenger hunt” of sorts, a food tour, and some wandering. San Juan is a beautiful old colonial town, one of the more built up in the Caribbean as it was a convenient first stop for ships coming from Europe on the Easterlies and looking for fresh water. Our food tour guide, a genuine boricua, seemed to have a foot in three worlds, the original indigenous people, centuries as a colony of Spain, and the recent period as an American after the “change of jurisdiction” (in which it become territory of but not part of the United States).

Public Art

They do it a lot and interesting stuff.

Yunque Forest in Puerto Rico

Dianne remembered finding a coqui frog last time she was in the Yunque and though we didn’t spot them this time we sure heard them. The Yunque is a rain forest, so, surprisingly, it rained. A lot. It’s some low mountains on the north eastern end of the island that take the brunt of the easterlies, pushing them up and getting them to dump their moisture.

Anguilla

A self governing British Overseas Territory that seems to be making a ton of money off of selling .ai domain names. And some tourism too. We slummed it on a day pass at the Four Seasons. Had a White Lotus feel, though no-one died. That we know of. Check back when they release the next season.

Antigua

An independent country but in the British commonwealth. We walked through St. John’s to Dickenson Bay Beach. We were surprised by how many signs there were of Chinese investment, including a large affordable housing complex. We were told the Chinese are very active in the Eastern Caribbean, making investments and loans.

The little museum in Antigua told a story, not of the Caribbean as a transit point for gold and silver (and hence an invitation to privacy and privateers) but instead of sugar and slavery. Five million African slaves were landed in the Caribbean. Most were worked to death growing and harvesting sugar. Sugar and indeed almost all industry is gone now, with tourism remaining.

Sint Maarten and St. Martin

The schizophrenic island, half French and half Dutch (according to our guide, the smallest split nation island in the world). We landed on the Dutch side and did a 22 mile tour that took us to the French side, around the lagoon, and back to the Dutch side.

Virgin Gorda

This island in the British Virgin Islands doesn’t have a whole lot going on. We skipped The Baths, saw them on a previous trip, but walked around Spanish Town.