The Windward Islands of the Caribbean have some of the most beautiful, uncrowded beaches in the world. They're dream territory for sailors, and a sailing trip is one of the best ways to see them.
I sailed around the islands on a tall ship with Windjammer Barefoot Cruises. They're now defunct, but a group of avid customers got together and resurrected a similar operation called Island Windjammers. These trips are a fun and relaxing way to get to even the smallest islands - the ones the big cruise ships can't reach.
You're literally in bare feet the whole time you're on-board - no formal nights on these vessels. And instead of sharing the decks with thousands of passengers, you mix and mingle with 12 to 30 guests over the course of your sailing. Accommodations are modest and a bit on the cramped side, but clean and well equipped. Especially considering what little time you'll actually spend in your cabin.
If you want to help raise the sails or take a turn at the wheel, the crew will welcome another set of hands. Or, you can sit back and sip your rum punch while you watch them do the work. Each morning, you wake up at a different tropical isle. You can choose to go ashore to tour the sites or relax on the beach as the mood strikes you.
May you have fair winds and following seas.