Bermuda
I’m cheating a bit about Bermuda here, since Zanshin hasn’t been there yet. But I did sail there as a crewmember of Challenge Accepted in the 2022 and the 2024 Newport-Bermuda Race, so I’ll sneak this country into my list. And perhaps one day I’ll visit the country with Zanshin as a stop between the USA and the Caribbean Island chain.
The links above go to my pages with all the pictures of the race, both mine and from the other crewmembers. It is a fun event, and each race was different, but both had a bit of everything during the course of the race. Storms. Calm. Water shortage. Power shortage. Equipment Failures. Good food. Great company.
I’d do that race again if offered the opportunity. I’m not sure that I’d sail my own boat there, though. It isn’t directly on the way, and it isn’t the cheapest of destinations, either.
Atlantic, not Caribbean
The country of Bermuda is not part of the Caribbean because it lies so far north. But due to the Gulf Stream it has a warm and congenial climate. It is, in my mind, the Switzerland of the Americas. It is not only clean and well-kept, but outrageously expensive. There is a lot of old money in Bermuda. It was the financial sector, not the agriculture (onions) which made this island affluent.
I haven’t had any chance to truly explore the island yet. Both trips so far were time-constrained at the end; most of my sightseeing was done while sitting in the back seat of my cab while driving to the airport the first time around. Had we done better during the race things would have been more relaxed, but in the end the timing worked to my advantage.