Monohull sailboats were the main yacht type when the charter industry started in the 1970s in the Virgin Islands. There are still excellent crewed sailboat charters in the British Virgin Islands and in the Caribbean. With two or more crew members, these yachts are a delight to sail and experience the wind in your face and seawater spray. There is nothing like sailing to windward on a monohull sailboat in a good breeze.
During the winter months, the winds can be quite strong which makes for excellent sailing in the Caribbean. Sailing in the British Virgin Islands and US Virgin Islands means shorter and enjoyable cruises. The Leeward and Windward Islands offer more open sea sailing with longer distances between islands.
Experienced sailors will enjoy sailing during the winter months in the areas of St. Martin, St. Lucia, and the Grenadines. From St. Lucia, you can sail south to the Grenadines on a one-way basis. Popular drop-off ports are Union Island in the Grenadines and Grenada.
Here is a selection of choice crewed sailboat charters in the Caribbean and the British Virgin Islands.