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, and typically 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 large majority of our clients fly in and out of, due to direct and more affordable flights. With a traditional start and end in the USVI, you'd typically spend one or two nights in and around the charming US island of St. John and the balance of the charter in the BVI. However and in the midst of COVID-19, many of our clients are also opting for USVI-only charters, with a full itinerary within US waters.
  • 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 with March and April also being key months as well.
  • 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.
  • 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.

A multi-repeat and 2 family group that we booked aboard 60' Catamaran Blue Pepper in the USVI in May 2021 said:

Hello Lynne, Denise, Taylor and Liz once again hosted an unforgettable experience for us and our families. Thank you Lynne for all you do to help us plan these fabulous trips!
Santiago P., Florida

Hi Lynne, Many thanks again for all your help in making our vacations memorable and truly outstanding.
German H., Florida

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, USVI 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.