A bareboat charter is literally bare of a skipper, crew and food. The chartered yacht is a floating vacation platform giving the part time sailor freedom of exploration. Bareboating in the Caribbean requires sailing experience and navigational skills. It also requires choosing a destination.
The Caribbean offers a variety of sailing options for different skill levels.The British Virgin Islands is perhaps the easiest due to line-of-sight sailing and two-hour island hops. Both the Leeward and Windward Islands are more challenging due to the open ocean sailing and distances between islands.
The Leeward Islands
The Leeward Islands span 200 miles. For sailors long on time, a few months provides time for an in-depth exploration. If you're short on time, focus on the three hot-spot bareboating islands: St. Martin, St. Barts and Anguilla (Renaissance Islands). Passages between theses islands are short and sail-satisfying. For longer and more challenging day passages, head for the tiny islands of Saba, Statia, or St. Kitts and Nevis. And to mix with die-hard sailors along with blow your socks off mega yachts, consider Antigua Race Week held each April.
The Windward Islands
The Windward Islands are at the southern end of the Caribbean chain. With pounding waves on the windward side and calm seas on the leeward side, the four main islands, Martinique, St.Lucia, St. Vincent and Grenada require ocean passages. The easiest passage is from St. Vincent to Union or Grenada. For a long passage, St. Lucia to St. Vincent is a hard day's sail with the return trip harder; this is for people who truly enjoy the sport of sailing. The Tobago Cays offer a chance for relaxation. Consider a one-way bareboat charter, which saves on time.
British Virgin Islands
The protected Britsh Virgin Islands is very popular among bareboaters due to the short hops and always being in sight of an island. Charter companies are located on Tortola, the largest BVI Island. The constant trade winds produce 10- to 25-knot winds year-round. From this mountainous island, you can set sail and seek out serene anchorages on more than 60 islands and cays. Jump off the swim ladder with your snorkel gear at the the caves at Norman Island. On low-lying Anegada, excellent snorkeling and diving is found among the hundreds of shipwrecks.