You used to have to be wealthy to go around telling people you are going to be sailing the Caribbean. It used to be a status symbol. It used to include a silly hat. But now nearly anyone can charter a boat or play captain themselves (experienced sailors only, please). Caribbean sailing vacations have been rising in popularity for a variety of reasons: prices to grab an experienced crew and take off into the unknown have fallen dramatically as of late (thought still a little too dependent on oil prices for some), and it's also an excellent option for a family vacation – it"s hard for the kids to avoid you on a watercraft. And more and more families are choosing the Caribbean as a vacation destination.

A Caribbean sailing vacation is also perfect for those who always feel fun is just on the horizon. You can zip in and out of as many islands as you want, and if you have your own boat, you can even drop anchor and sleep under deck, saving large chunks of cash that normally would've gone to hoteliers.

But for most of you sailing the Caribbean, you will be chartering a boat. While some crews will advertise on the internet and with travel agents, it is just as easy to find someone to take you around the islands when you reach them. Travel agents can sometimes find cheaper fares, plus they are almost always guaranteed to be reputable boats. Most of the scam artists are run out of town by the other sailors, though – they understand that the competition is thick, so poor reports from a Caribbean sailing vacation reflect upon them all.

The second most important issue when sailing the Caribbean is where to go. Some islands are well-known for having above average sailing, but it"s quite hard to find a bad spot. Ask around and you are invariably going to get excellent suggestions. But the most popular areas for Caribbean sailing include the Virgin Islands, both American and British. Since they are so close together, you can jump back and forth between the two, and there are plenty of deserted islands to occupy your time. The Turks and Caicos Islands are much the same way, though their ports are less crowded.

Sailing the Caribbean is definitely more popular in the Lesser Antilles islands (St. Martin, St. Kitts and Antigua). Shoving off in St. Martin, you can easily skip between both sides of the island, head over to Anguilla, St. Barts, and the smaller southern islands of Saba and St. Eustatius.

But no matter where you choose to begin your Caribbean sailing vacation, you will find what you are looking for and what the islands are famous for – great views of turquoise waters, bone white beaches and the constant feeling of moving forward, the simple act of exploration.