Sailing
From 1990 to 2001 my friends and I rented a sailboat that William Frank captained and we crewed. During this time we sailed in waters off Italy, Cape Cod, the Bahamas, Grenada, St Martin, St. Lucia, Nevis, and others. William died in 2017, so from 2019 to 2023 I hired a captain, and my grandsons and I sailed off St Barts, the BVIs, and the Bahamas.
I'm slightly less agile these days and do most of my sailing on cruise ships. Not that I was ever much of a bareboat sailor--Mike was much better. However, I still think of sailing as a terrific hobby and great fun.
It's not a rich-man's sport. In fact, it's an inexpensive way to vacation if you're prepared to rough it and deal with the occasional mishaps. Most sailboats, for example, cost less than $1,200 a day, including a captain and provisions. That's $200 / day / person with six people sailing. This is a small fraction of what it would cost to: vacation at a Caribbean resort in an ocean-facing room, visit 5 or 6 nearby islands, swim on deserted beaches, dine and drink in exotic anchorages.