Caribbean Sail Yachts
Classic Sailing Meets Timeless Elegance
For many guests, a crewed sailing yacht is the purest way to experience the Caribbean: the trade winds filling the sails, the engine off, and a new island on the horizon. We arrange crewed sailing yacht charters from 44 ft to 289 ft, from performance sloops to classic schooners and modern sailing superyachts, each with a professional captain and crew.
Why charter a sailing yacht in the Caribbean
- Reliable trade winds: the eastern Caribbean has steady easterly winds for much of the year, ideal for relaxed, exhilarating sailing.
- A quieter, greener way to cruise: long stretches under sail use little fuel and let you hear the sea.
- Character and craftsmanship: classic and custom sailing yachts are some of the most beautiful vessels afloat.
- Get involved or relax: take the helm, trim the sails or simply watch the crew at work.
Best Caribbean sailing grounds
The British Virgin Islands offer short hops and sheltered water, ideal for a first sailing charter. Antigua and the Leeward Islands add longer passages and famous regattas, while the Grenadines and the Windward Islands reward experienced sailors with open-water sailing and uncrowded anchorages.
Monohull or catamaran?
A monohull sailing yacht heels under sail and delivers the classic sailing feel, and larger monohulls are especially comfortable in open water. A sailing catamaran sits flat and offers more living space for its length, which many families prefer. Your broker can help you weigh the trade-offs for your group.
How much does a crewed sailing yacht charter cost?
Rates depend on the yacht, crew and season. Smaller crewed sailing yachts can be all-inclusive, while larger sailing superyachts are usually chartered plus expenses, with an Advance Provisioning Allowance (APA) for food, drinks, fuel and dockage. We give you a full cost estimate, including taxes and suggested gratuity, before you book.
Why book with Caribbean Yacht Charters
We are an independent broker, part of Sneed Tropical Yacht Charters, arranging crewed charters since 1990. We know the Caribbean sailing fleet and its crews and recommend the right yacht at no extra cost to you. For a broader planning guide, see our Caribbean sailing vacations page.
Ready to compare yachts? Send us your dates and group size and a broker will reply with a shortlist of available yachts, or call (561) 463-6840.
Caribbean sailing yacht charter FAQs
Do I need to know how to sail?
No. Crewed sailing yachts come with a professional captain and crew who handle the sailing. You are welcome to help, take the helm or learn as much as you like.
Will the yacht heel a lot?
Monohull sailing yachts do heel under sail, and the captain can keep the motion gentle by choosing routes and sail settings to suit your group. Guests who prefer a level ride often choose a catamaran.
What is the best season for sailing in the Caribbean?
December through May brings the steadiest trade winds and the driest weather. Hurricane season runs from June through November.
Can I join a regatta on a charter yacht?
Some charter sailing yachts take part in Caribbean regattas such as Antigua Sailing Week and the St. Maarten Heineken Regatta. Ask your broker which yachts accept regatta charters for your dates.
