Caribbean Yacht Charter Vacations

There are four main areas to choose from for your Caribbean yacht charter vacation, including our popular British Virgin Island (BVI) Charters, our US Virgin Islands Charters (which start and end in St. Thomas, but spend a majority of their time in the BVI), charters in the Grenadines, plus charters in and around the St. Maarten and St. Bart's area. We additionally offer crewed yacht charters in the Bahamas. After determining which destination suits you best, we'll expertly match you with the ideal yacht and crew for your Caribbean yacht charter, at no additional cost to you.

Which Destination Is Right For You?

Discover more about each destination or contact us directly so that we can help you determine the right decision for your yacht charter vacations.

  • BVI: Our most popular destination choice.This destination features an abundance of yacht options, protected and easy BVI sailing vacations, plus plenty of islands, anchorages and activity options. Extremely well suited for family charters or first timers.
  • USVI: This is where a majority of our clients fly in and out of, due to direct and more affordable flights. Your yacht may be willing and able to pick up and drop off here. If not, you're just a ferry ride away from your yacht of choice in the BVI. When you start and end your charter in the USVI, you'll most likely spend one night off the charming US island of St. John.
  • The Grenadines: This destination is ideal for those in search of a true Caribbean experience. The Grenadines is slightly more difficult to reach and therefore more expensive in terms of flight costs and travel time to get there. Visitors will be rewarded with a more unspoiled, authentic, and therefore memorable experience on their charter. After the Virgin Islands, the Grenadines continues to be our 2nd most sought after destination.
  • St. Maarten/St. Barts: A charter in this area typically encompasses the three islands of St. Maarten, St. Barts and Anguilla. This area has a definite European flair and is best visited during the summer months of June through early August. During the winter months, the constant trade winds and occasional north swells can shut down many of the available anchorages within this area. Visitors to this area will enjoy visits to the Dutch and French side of St. Maarten, French St. Barts, plus Anguilla.
  • Bahamas: A yacht charter vacation in the Bahamas is perfect for those in search of an experience off the beaten path. With a start and end in Nassau, the Exumas chain on the southern end of the Bahamas, are easily accessed from the States yet remain unspoiled and unique. May, June and July are ideal months for vacation yachting in the Bahamas.

A family that we booked aboard 62' Catamaran Anastasia for New Years 2017/2018 said:

We had an incredible time! We all rated it as one of our top family vacations. I really want to thank you. When I had the idea that chartering a boat in the Caribbean might be something we wanted to do, you quickly responded. You answered all my questions and suggested great options for our family. Anastasia was the perfect catamaran for our trip! Feel sure our family will see them again in the future. Thank you Lynne for all your help.
Tahnee B., Texas

More From Carefree Yacht Charters®

Holiday and Spring Break Charters

It's never too early to book your Christmas, New Years, or Spring Break charter in the BVI or other Caribbean destination. Top yachts and crews secure bookings up to one year in advance for these popular holiday time frames. While the BVI is by far the most popular destination, we encourage you to contact us directly regarding your interest in other areas, including charters from the BVI to the Grenadines.

Yacht Special Offers

View our yacht specials to discover which of our catamarans and power catamarans are currently offering enticing specials.

Crewed Charter Choices

Explore our popular picks within each yacht style category including catamarans, monohull sailboats and luxury motor yachts. View our entire list of catamaran charters or power catamaran charters. Or, contact us directly to guide you through the entire crewed charter selection process.

The Crewed Charter Yacht Experience

Personalized and private, embark on the vacation of a lifetime! Learn more about what these Caribbean yacht charters offer.