A luxury yacht charter with crew in the BVI, USVI, Caribbean or Bahamas can prove to be a truly unique and extraordinary vacation experience. The on-board experience will ultimately depend on selecting the right yacht charter broker from well-known yacht charter companies. Important elements to consider when selecting a yacht charter broker include their level of expertise plus their typical pre charter process. In other words, think of your overall experience as having two phases, including the all-important pre charter experience along with the actual on-board vacation experience that gets delivered


What is a Luxury Crewed Yacht Charter?

Luxury means different things to different clients and different yacht charter companies. At Carefree Yacht Charters, luxury isn’t necessarily defined by our client’s budget range or the size or type of yacht they choose. Rather, many of our clients define luxury as “an absence of worry”, knowing that their handpicked yacht & crew will be ideally matched to their group, that the largest and smallest of charter details will be expertly handled in the background, and that their transition from our planning stage to their stepping aboard on day 1 will be seamless. With 25 years of experience on both the crew and broker side of the business, we’ve perfected the art of delivering a smooth, easy, and carefree experience from start to finish. Our clients can relax while we do the heavy lifting.

A group of sisters & girlfriends that we booked aboard 52’ Island Hoppin’ in April 2019 said

The islands and coves we visited and moored in, left permanent images of beauty in our minds and hearts, sunsets to beat all sunsets and a sense of being so far removed from reality that there was no room for worry. Someone once defined luxury as "the absence of worry" well that is what Jamie, Susannah and Island Hoppin provided for us... complete and total luxury! A big thank you to Lynne from Carefree Yacht Charters for connecting us with this wonderful boat and crew!
Beth B., Colorado

What Makes Our Pre-Charter Experience Unique?

  • As many of our clients realize post charter, the crew can make or break the experience. At Carefree, we’re all about matching our clients with crews and make it a top priority to get to know the crews on a more personal level. This allows us to not only recommend the right crews for our clients, but to also send the right clients to our crews. It’s a win-win situation.
  • We developed our pre charter process based on 12 years as crew and over 300 weeks of charter on our own crewed yachts in the BVI, USVI and Caribbean. We were on the receiving end of some less then ideally planned charters during our tenure and developed many of our best practices as brokers around that. We know first-hand what these charters look and feel like and that experience has proved invaluable for our clients.
  • With an additional 13 years in business as Carefree Yacht Charters and our consistent ranking as a top yacht charter company in the BVI, USVI and Caribbean, we’ve quite simply perfected our trade. As one of the premier yacht charter companies in the industry, we also set the bar extremely high for our crews and expect them to deliver on our charters. Our high percentage of repeat clients and their referrals is a testament to what we do.
  • When combined, we are uniquely qualified to expertly handle your trip of a lifetime. Once you’re ready to move forward, learn more about our Carefree Booking Process.


A family that we booked aboard 65' Motor Yacht Cool Breeze for New Years, 2018-2019 said:
My family had the trip of a lifetime. As for Carefree Yacht Charters, you did a great job sticking to your guns about the right fit for my family. There are cheaper ways to do this type of trip, but none with the same outcome, and you were good at explaining that. Your process is very thorough and seamless. The organization of your process made everything go smoothly. Thank you very much."
Scott S., Maine

A group of couples that we booked aboard 52’ Island Hoppin’ in May, 2019 said:
This vacation was a dream come true for us. Lynne, you matched us with a boat and crew that fit us just right. You were always so easily available and made the process of booking very easy. Having the logistics of a trip taken care of, you really allowed us to be carefree in the time leading up to the trip. The company is well named."
Chris and Lauren G., North Carolina

A group of couples that we booked aboard 50' Catamaran Gambit in March, 2019 said:
Being a first timer, I had expected sun, fun, and relaxation, but I had no idea the bounty of other elements that make for a magical week. I would like to thank you for laying the groundwork for our trip. I now understand the importance of matching a boat and crew to the pace and style of the guests, and you did that perfectly. Best wishes to you and thank you again for all you did to make our trip nothing but smooth sailing."
Meg C. Virginia

See what additional clients have said and learn more About Us.


Here’s two key questions that many of our clients ask us in their initial stages. In order to maximize your charter experience for your group, it’s extremely helpful to speak with you directly. Contact us today and let’s get started.

  • What questions should I be asking? Many of our first-time clients want to know what questions they should be asking us. That’s where 25 years of experience on all sides of the business add a tremendous amount of value. From the first phone call, to expertly matching clients with crews, and everything in between until the day you step aboard, we are hands-on and will guide you through our charter process. This unique process will provide you with all the key details plus likely answer some questions you never knew you had. As crews consistently tell us, our clients step aboard fully prepared for their charters and with meaningful expectations about the experience ahead. Crews often say that we “always send them the best guests”, which confirms that our match-making skills have once again come into play.
  • Which yacht and crew is right for me? With so many yachts and crews available online, how do you choose? We inspect these yachts annually, get to know these crews on a personal level, and receive loads of feedback for the charters that we book. This allows us to continually refine our list of recommended options and weed out the others for our clients. While some yachts and crews are best for couples, others are ideal for family groups. While some crews are well suited for a group of foodies, others make outstanding picks for more adventurous groups. Some have high energy, and some are laid back. Your style and specific interests are key and differentiate your charter group from the next. With that in mind, the more we know about your style and what’s most important to you and your group, the better we can match you with the recommended yacht and crew that fits you best.

Please read our FAQs page for more details and common questions regarding the charter experience.




Watch a short video featuring 62’ Catamaran Seahome to get a glimpse of the BVI and USVI crewed charter experience. Seahome is one of our favorite high-end, exclusive selections with accommodations for up to 10 guests in 5 Queen cabins.

What Makes Our Luxury Yacht Charters So Extraordinary?

  • Ryan & Jill, a favorite crew on 52' Catamarn Oui Cherie

    Ryan & Jill, a favorite crew on 52' Catamarn Oui Cherie

    The Crew: Imagine a Captain and private Chef whose sole desire is to cater to your every whim and specifically tailor your charter around you and your group. You will eventually fill out our online preference form which will gather specifics regarding the guests in your group along with your activity, food and beverage preferences. This form has been continually refined over time and allows the crew to “get to know you” before you arrive. The Chef will create a menu based on your preferences and dietary requirements, the yacht will be appropriately stocked when you step aboard, and the Captain will have a general plan about the course he’ll suggest based on your interests.

  • Your Itinerary will be based on your Preferences

    Your Itinerary will be based on your Preferences

    Multiple Island Visits: Visit a new island each day, each with its own unique character and charm. Once you’re aboard, the crew will do all the work, allowing you to sit back and take it all in. Or, if you’re looking to learn or be active on your charter, you can jump right into the action. You’ll quickly discover that some islands offer amazing snorkeling, beautiful beaches to explore, the perfect anchorage for loads of water sports, or that adventurous hike rewarded with views. You’ll also see that some islands offer it all and you’ll have to pick and choose among the various options each day. Your crew can keep you abreast of your itinerary and the various options so that you can plan your days activities accordingly. We have loads of insight regarding the best itineraries so don’t hesitate to ask us about the must-see locations as well as some off the beaten path favorites.

  • Carefree clients at "The Baths" on Virgin Gorda

    Carefree clients at "The Baths" on Virgin Gorda

    Flexible itineraries: In contrast to a cruise ship or some of the cookie-cutter charter options out there, your itinerary and crewed charter experience is extremely flexible. It is ultimately based upon the vacation pace you set once aboard along with what you’d like to do and see. The Captain and crew can easily adjust their itinerary choices based on what you’re enjoying the most as well as the weather at hand as the charter progresses. The true beauty of these crewed charters is that there is no need to plan every detail in advance, rather allow your crew to tailor the charter on the fly. Our typical charters are 7 nights in length and those provide the most flexibility and relaxed pace. On average, you can expect to spend about 1 ½ to 2 ½ hours of easy movement between the various islands each day, whether motoring and/or sailing. The balance of your days will be spent in one of the beautiful anchorages, giving you plenty of time to relax, engage and explore.

Here's how one Carefree Client Described his On-Board Experience:

A group of couples that we booked aboard 45' Catamaran Great Adventure in February, 2019 said:

Our recent trip to the BVI turned out perfectly. Much appreciation to your initial suggestions and guidance that led us to the Great Adventure, a 450 Lagoon that was very clean, well-appointed and sea-worthy in every regard. Nice to have a vessel where everything works and our group of 3 couples fit very nicely in our state rooms and on-deck. Our venture started with 4 possible companies and quickly narrowed to Carefree Yacht Charters because of the clear and quick information you provided to us for our first-time sail. Your communication throughout the planning stage was very timely, professional and accurate, and your guidance on what to expect was perfect. Our group has power boated for many years and this would be a first sail venture and boating where we were not in charge. It was a welcomed departure from our boating routine.

We had a general idea on what we wanted to see during the week and planned to rely substantially on suggestions from the Great Adventure crew to narrow the focus. Very glad we did, since Conor and Taylor had superb ideas and recommendations based on our pre-sail call and our first day onboard. We made further small changes in itinerary along the way based on timing and weather. Their recommendations were always spot-on. The variety of the islands made each day unique, both in travel to an island but also the activities available on an island. Great Adventures was well-appointed with any water toys that we wanted to use once we arrived at a destination. Our adventure on this sail reached our expectations and beyond. The weather was just as great as advertised and the islands are diamonds in the sea with pristine beaches. All of us reached a level of relaxation slightly above a meditative state.

What caused this venture to excel the most, however, was the crew. I think Conor's bio on your website is understated just as he is modest about his knowledge and skill. He is very talented and possesses judgment of a much older captain. Our safety was always prominent in his decisions on one hand, while being very accommodating to our enjoyment on the other. He had total command of Great Adventure. As we watched other vessels maneuver nearby, we were happy we were onboard the Great Adventure. All of this was enough to cement our best trip ever, but we enjoyed a bonus in the cuisine offered up for meals by chef Taylor. It is hard to fathom she could have achieved that level of culinary expertise by now but we experienced it each day - each meal. We found ourselves takings pictures of the presentation before we devoured each meal. Each meal was delectable and healthy and portioned just right. Taylor would describe the ingredients of each meal as she served it and mentioned preparation techniques as well. There was a complexity to most of the meals that revealed her talents. An hour after lunch, we were plying her on what's for dinner and she would playfully demur until its reveal. Lastly, what we did not fully expect was the wonderful interaction we had with Conor and Taylor. They are very interesting, accomplished and engaging. We enjoyed lots of good conversations. Somehow, they also managed to handled all of what was required to move our adventure forward and make it great.

Bob R., Colorado

More From Carefree Yacht Charters®


It's never too early to book your Christmas, New Years, or Spring Break charter in the BVI, USVI other Caribbean destination or the Bahamas. Top yacht charter companies and crews secure bookings more than one year in advance for these popular holiday time frames. While the BVI and USVI are 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 as well as the Bahamas.


Discover which charter type suits you and your group best, such as our popular family charters, couples charters, or more adventurous dive charters. Learn more about all of our charter types.


Enjoy the islands aboard one of our catamarans, power catamarans, traditional motor yachts or monohull sailboats. Learn more about our various yacht styles.