If you like being on the water and aren't prone to seasickness, one of the best vacations you can ever have is chartering a catamaran in the Caribbean. A sailboat gives you independence and freedom to island hop, explore, anchor in hidden coves, snorkel, scuba dive, or just kick back. I wrote an article for GoNomad on a bareboat charter, which we did last April in the French and British West Indies. I also wrote an article on sailing to Terre-de-Haut, Guadeloupe for the Los Angeles Times.

The most important consideration when planning a charter is to choose your crew very carefully. Although a catamaran is spacious by boating standards, tight quarters equates to no escape from others onboard. Family members whom you get along with work well. Friends who all know each other work well, otherwise there might be personality conflicts among people who have just met at the inception of the trip. Flexibility among everybody is a must. If you're used to dictating policy at your job, that will not go over well with a group of people on a boat. There's no time for prima donnas or slackers. And, lastly, if you don't like sailing, don't go. It only takes one sour grape, or two, to ruin a bunch.

Personally, I charter with Sunsail, I have found that they have the best rates for the same catamaran, or monohull that can be found at the Moorings. The Moorings is very popular among non-sailors in the British Virgin Islands. They hire a captain for a week for short sails between islands. I have actually spoken to people who will charter with the Moorings just because of the name. Whatever floats their boat -- no pun intended. Footloose is another option, which is owned by the Moorings with lower rates.

Both Sunsail and the Moorings have bases worldwide.