Caribbean, USVI & BVI Yacht Charters

At Carefree Yacht Charters, we specialize in arranging extraordinary crewed yacht charters in the BVI, USVI, Bahamas and other Caribbean destinations.

Looking for a Private Crewed Yacht Charter? At Carefree Yacht Charters^®, we specialize in arranging extraordinary crewed yacht charters in the BVI, USVI, Bahamas and other Caribbean destinations. Choose from our extensive list of yachts, including our popular luxury crewed catamaran charters and higher end power catamaran charters. Learn more about us, including what our clients say.

Why Choose Carefree Yacht Charters? Experience matters. We're a top 5 Crewed Yacht Charter Company with over 25 years of industry experience. Our tenure includes 14 years in business as the Owners and Brokers of Carefree Yacht Charters plus 12 years as the Owners and Crew of our own highly successful yacht in the BVI, USVI & Caribbean. When combined, we are uniquely qualified to expertly handle your vacation of a lifetime. Contact us today and learn more.

What Should You Be Thinking About Now?

Think USVI as your Best Domestic Destination Plan thru July 2021...
If you're considering a charter between now and July 2021, then you should keep a USVI only charter in mind as your best domestic destination plan. Since their initial opening on June 1, 2020, we've had numerous client groups charter in the area with rave reviews and without issue, including numerous repeat clients whose itineraries previously included both the USVI & BVI. With extremely simple entry protocols, and as the USVI is a domestic travel destination, the USVI remains as your easiest and therefore safest destination choice in the short term.

Think Christmas 2021, New Years 2020/2021 & Beyond...
With a return to normalcy on the horizon, we already have a long list of clients looking to plan their next escape! If you don't want to "miss the boat" so to speak, you need to plan ahead for Christmas 2021, New Years 2021/2022 and Spring Break 2022. With Christmas 2021 less than a year out, let's get planning today in order to get you aboard that perfect yacht and more importantly, with that ideal crew for you!

Yacht Options

Choose from our extensive lists of yacht options, including our luxury crewed catamarans or our higher-end power catamaran and motor yacht charters. Not sure which yacht style suits you best? Learn more about our yacht options.

Catamarans

Our popular favorite due to an array of yacht options, on-board space, & stability. View our full list of catamaran options.
Photo Credit: 62' Catamaran Sea Wings II

Power Catamarans

Featuring luxurious, modern amenities plus quicker mobility around the islands. View our full list of power catamaran & motor yacht options.
Photo Credit: Horizon PC60

Monohulls

Perfect for the traditionalist in search of a more adventurous sailing experience. View our full list of monohulls sailboat options.
Photo Credit: 72' Monohull Pacific Wave & Yacht Shots BVI

Learn More About Yacht Options

Charter Areas

Select from our popular BVI sailing vacations or opt for a US Virgin Islands Yacht Charter, which includes a convenient St. Thomas start & end on your private crewed charter. Learn more about our Other Charter Areas, including authentic charters in the Grenadines or more remote charters in the Bahamas.

USVI: US Virgin Islands

Easy access including direct and affordable flight options to this US Territory. See our featured USVI charter selections.

BVI: British Virgin Islands

Our #1 Destination and a popular pick for families or couples. See our recommended BVI Crewed Charters.

BVI: British Virgin Islands

The Exumas,
Bahamas

A remote and pristine charter destination that is off the beaten path. Learn about the Bahamas yacht charters.

Learn More About Charter Areas

Charter Types

We offer ideal yacht and crew selections for family vacations, sailing vacations for couples or honeymoon and anniversary charters. Learn more about our Charter Types.

Family Charters

Our #1 Charter Type with an abundance of family-friendly options. View our featured Family-Friendly picks.

Couples Charters

We know the best yachts and crews for couples charters. View our featured Couple selections.

Anniversary Charters

A luxury crewed yacht charter is an ideal way to celebrate! View our featured Anniversary charter options.

Specialty Charters

Is on-board scuba, a Chef that caters to Foodies, or the ability to accommodate a large group of guests key? Learn more about our Specialty Charters.

Dive Charters

Count on Carefree Yacht Charters to recommend the best dive yachts and crews for your charter. View our featured dive selections.

Foodie Charters

Culinary trained Chef's and high end cuisine are the key criteria that set our Foodie Charters apart. View our Foodie picks.

Tandem Charters

Perfect for groups of 10 or more with multiple yachts & crews sailing in tandem. Learn more about tandem yacht charters.

Learn More About Charter Types

A family that we booked aboard 52' Catamaran Grace in July 2020 said:

Both Lynne and her husband were incredibly responsive, by far the most 'on top' of the communication protocols over all the other brokers I reached out to at the start of the process. Lynne is the perfect balance of authority, active listener and deal closer that makes an expense of this magnitude feel 'comfortable' and something that will provide deep value. I felt like I had a partner who was as invested in this experience as my family. Thank you much, You did a really wonderful job.
James M., North Carolina

Contact Us

Call us in our South Florida office at 954.980.9281, Toll Free at 888.670.6884, or complete our Quick Request Form.

We’ll quickly match you with a charter yacht vacation that fits your group’s interests, style and budget.

Looking for a specific yacht? We can assist in brokering any yacht out there or that you're interested in. Rely on our expert advice about the best yachts and crews so that you can go on to enjoy your vacation carefree, as it should be.