The first time I ever heard about chartering in the Caribbean was from a friend, Bob Palmer, on whose boat, No End, I used to crew on Wednesday night races during the summer, out of Oswego, NY on Lake Ontartio during the late 1990s.

One day after a race, Bob was discussing a week-long Caribbean vacation charter he was planning with his family for the upcoming winter. I asked what it was like.

His story started very similar to that on my Home page:

Wake up, whenever (no alarm clocks, no early agendas). Have some coffee. Go for a swim in the warm clear water. Have breakfast. Have a cocktail... WITH breakfast, if you like. Enjoy your company and your views. Plan on where you want to sail to for the day. Have lunch. Go for a swim or snorkel. Dry off in the warm sun. Release your boat from its mooring and start sailing to your next destination. This is all “line of sight” sailing, usually several hours at most, but this doesn’t preclude you from exploring along the way, or sailing for the fun of it. Pick up a mooring or anchor near a beautiful deserted beach. Swim, snorkel or dinghy to shore. After exploring for awhile make your way back to your boat and have a cocktail. Enjoy dinner aboard your boat and enjoy the sunset, perhaps with another cocktail. The time passes slower, because you are savoring every moment. After an enjoyable evening, make your way to your bunk and get gently rocked to sleep.

Rinse, Repeat.

I have found that every charter in the Caribbean (At least the ones I’ve been on!) follows a very similar relaxing pattern. It doesn’t get old because you are in a different place every day.