Caribbean Yacht Charter Destinations

There are four main areas to choose from, including our popular BVI Yacht 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 area. After determining which destination suits you best, we'll expertly match you with the ideal yacht and crew, 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 destination for you and your charter group.

  • BVI: Our most popular destination choice. This destination features an abundance of yacht options, easy and protected sailing, 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. This destination is ideal for charters during the months of May, June and July.
  • Belize: A charter yacht vacation in Belize is well suited for those in search of an off the beaten path experience in a quiet, remote and pristine area. Belize is the ideal combination of uncrowded anchorages, paired with crystal clear waters for diving and snorkeling.

A family group that we booked aboard 76' Tranquility for New Years 2016/2017 said:

The crew, the yacht, the food, and the BVIs were all fantastic. Our charter experience was amazing in every respect. I really did appreciate the quick follow-up from you and the online preferences form. It made it very easy to send information efficiently. Thank you.
Bud C., California

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, sailboats and motor yachts are currently offering enticing specials.

Crewed Charter Choices

Explore our popular picks within each yacht style category including catamarans, sailboats, plus motor yachts. View our entire list of catamaran charters, sailboat charters or motor yacht 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 charters offer.