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.

Caribbean & BVI Yacht Charters

What Should You Be Thinking About Now?

THINK SUMMER 2022 & HOLIDAYS 2022/2023...
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 Summer 2022 and New Years 2022/2023. With Christmas 2022 less than 18 months out, let's get planning today in order to get you aboard that perfect yacht and more importantly, with that ideal crew for you!

Think USVI as your Best Domestic Destination Plan thru July 2022...
If you're looking for a luxurious yet simplistic getaway between now and July 2022, 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.

Yacht Options

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


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 options.
Photo Credit: Horizon PC60

Motor Yachts

Ideal for the discerning client in search of top-notch service and on-board amenities. View our full list of traditional motor yacht options.
Photo Credit: 92' M/Y ELITE

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

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

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.

A multi-repeat family that we booked aboard 62' Catamaran Anastasia in July 2021 said:

Hello Lynne, Well, I can’t say enough about how wonderful our trip was. This was our third charter and it was an awesome experience for all of us. After the first charter, I remember saying how that was truly the trip of a lifetime and we could never top it but, as they say, “never say never”. I have told many friends about our trip and they always ask who I used to book it with and my response is always the same: "I wouldn’t use anyone but Carefree Yacht Charters". Sounds like a commercial but it's the truth. You have always been available for questions and your suggestions and recommendations are always spot on. You make the whole process a breeze. In summary, our entire time on board the Anastasia yacht was something out of a dream. Thanks again for all you did to make it happen.
The Simms Family, Arizona

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.