An all-inclusive family yacht vacation is an amazing way to enjoy quality family time plus create those vacation moments that you’ll never forget.

With a perfect balance between luxury, adventure and an escape to paradise, our family catamaran charters in the British Virgin Islands (BVI), US Virgin Islands (USVI) and Caribbean have something for everyone. Enjoy sugary sand beaches, sun-soaked days on the water, family dinners under thousands of stars and so much more.


  • Fun for Kids: Forget boring. With action-packed activities and a new island to explore each day, our family-friendly charters and crews will captivate your kids from Day 1. From learning to sail, snorkeling with sea turtles, tubing for hours, treasure hunts or theme nights, even scuba diving on some yachts, big smiles and the anticipation for what comes next await.
  • Rejuvenating for Parents: Sit back, relax and take in the breathtaking views or rediscover your inner child and jump into the action and adventure with your kids. You can be as laid back or active as you want. It’s your choice to make each day. With all the logistics left to the crew, you’ll be amazed at the amount of quality family time you get to enjoy as each day unfolds.
  • All inclusive family vacation: Other than a standard crew gratuity, these charters include the yacht, your professional crew, all meals, standard bar, plus use of all on-board water sports, including scuba diving on some yachts. Once you step aboard, you can tuck your wallet away and simply enjoy everything the yacht and a new island each day has to offer.

Request a Quote

Call us in our South Florida office at 954-980-9281 or Request a Quote. We'll quickly match you with a family charter that fits your budget, style and interests. Or, get started by viewing a sampling of our popular family sailing vacations.

A family that we booked aboard 62' Catamaran Anastasia for Christmas 2021 said:

We had the best vacation of our lives aboard the Anastasia with Ryan and Lesli as our crew. First of all, Lynne, your able management and impeccable communication made for a seamless pre-trip experience. Our week on the Anastasia will be a cherished memory for our family for years to come. We absolutely hope to replicate it in the future, but nothing will ever replace our incredible first time charter experience. Thank you, Lynne, Ryan and Lesli, for making it happen. All our best,
Eloise P., Massachusetts

Family Sailing Vacation Options

Holiday Charters

Leave the hustle-bustle of the holiday season behind and unwind with your family aboard a crewed charter instead. Your professional crew will custom tailor the charter to ensure that every family member gets the holiday vacation they’re after. Christmas or New Years are the most popular weeks of the year, the islands are filled with excitement and energy at this time of year.

Spring Break Charters

Spring Break brings to mind thousands of college students descending on a beach town. A Spring Break family yacht vacation is the exact opposite. Your yacht will be anchored in a turquoise bay, with appetizers on the flybridge, and your favorite tune on the stereo. Spring Break on a yacht is all about vacation experiences with family. Spring Break vacations continue to fill earlier and earlier each year so as soon as we know your Spring Break dates, it’s important to get you with a yacht and crew ideally suited to your family’s adventure level and style.


Charters in the BVI remain as our #1 pick for a family sailing vacation in the Caribbean with their abundance of white-sand beaches, easy sailing between the islands, plus the most yacht options at every price point. Your family will love that it’s all about being in and around the water. Snorkel into pirate caves, check out underwater swim throughs, jump off cliffs, experience the latest water toys or take an exhilarating hike up to one of the amazing viewpoints of the islands. Plus, if your family or kids are a little bit older, the BVI also offers some of the coolest beach bars in the world.



Consider a tandem charter with another yacht or two, a popular family option across Spring Break weeks or during the summer months. This charter option offers many of our clients the best of both worlds. Kids get the time with their friends that they crave and adults get to enjoy quality family time along with a luxury vacation experience. These family tandem charters are ideal for those looking for some vacation overlap with other families and their kids, without compromising their private family experience.


If you’re looking for a fully shared experience, team up with another family and split the cost of a larger and more luxurious yacht. This cost-sharing option is a perfect way to enjoy a more affordable family vacation in the Caribbean. Adults can revel in the food, service and on-board luxuries while kids get to spend their days having fun with their friends. With our 8-guest and 10-guest catamaran options offering 4 and 5 guest cabin layouts, there’s plenty of on-board space to gather with the group or to take in a quiet moment as well.


We break our all inclusive family yacht charters into 3 price point categories including our affordable favorites, mid-range luxury options plus high-end, exclusive selections. The majority of our crewed charters are all inclusive, including the yacht, the crew, all meals, standard bar, everything it costs to run the yacht, plus use of on-board water sports equipment.

  • More Affordable Favorites: This popular category features yachts that fall in the $20,000 to $35,000 range, plus tip and is well suited for many of our family groups of up to 8 guests. The majority of the yachts in the price range are in the 46’ to 56’ range. Many of these yacht options include younger, energetic crews, ample space on-board, plus the latest water sport toys.
  • Mid-Range, Luxury Options: Step up to this category and you’ll often be considering options from the 50’ range to the 62’ range that fall in the $35,000 to $50,000 range, plus tip. These yachts offer expanded space in the cabins, the main gathering areas, plus on the upper fly-bridge decks. Depending on the size of the yacht, you’ll sometimes increase to a crew of three. These additional crew members have dedicated roles aboard and therefore offer an added layer of service.
  • High-end, Exclusive Selections: The yachts in this category typically fall in the 62’ to 80’ range and with price points ranging from $50,000 to $100,000, plus tip. Crews of 3 to 4 including a Captain, Chef, plus either First Mate and/or Stewardess are common aboard these larger and often newer yachts. This step up includes yachts with expansive space, a formally trained chef, plus high end watersports equipment such as Seabobs and E-Foils.

Learn more about the cost of chartering a yacht in the BVI, USVI, Caribbean or Bahamas.


  • Will there be enough to keep my kids entertained? On our family crewed yacht charters, there is an abundance of daily activities as well as learning opportunities for kids. From learning to sail, snorkeling with sea turtles, tubing for hours, even scuba diving on some boats. Every day is a little different, has a new and unique anchorage to explore, and that constant change in scenery keeps kids both entertained and engaged.
  • Can we charter for fewer nights? The majority of our family charters and in particular, our repeat family charters are 7 nights in length. That said, with kids busy schedules, sometimes 7 nights just won’t fit. Six night charters are popular with busy family’s and as they are discounted in a prorated fashion, they offer a budget friendly alternative as well.
  • My kids are picky eaters. Can the Chef’s aboard these yachts cater to that? Absolutely! Our recommended Chef’s are accustomed to creating simplified kid versions or “kids meal options” for their family charters. You’ll fill out our online preference form which will allow you to detail what your kids will enjoy and just as importantly, what your kids won't eat. Also, with a creative Chef aboard, you may be surprised to see your kids perhaps hanging around the galley and discovering some new and more adventurous foods on charter.
  • How is chartering a yacht with a family in the BVI different from other Caribbean destinations? The BVI is the top sailing destination in the world and is perfectly suited for a family charter vacation. The islands are close together and well protected, making for easy line of sight sailing. Each island also has a unique and authentic feel, keeping the adventure level high. Jost Van Dyke boasts white sand beaches and world famous beach bars like Soggy Dollar, consistent favorites for families with young adult children. Virgin Gorda and The Baths, combine a collection of massive granite boulders, secret pathways, crystal clear water and white sand beaches - there’s really no other place quite like it.
  • How is a family yacht charter different from a family vacation at a resort? A crewed yacht vacation is truly an escape to another world. You leave congestion, lines and strangers behind and it will be hard to return to resort life after the excitement of a yacht vacation. Your yacht will move to another unique Island each day and that anticipation and discovery can’t easily be replicated at a resort. Families return year after year telling us that the quality family time and ability to experience things together is what makes these sailing vacations so special and different.

More From Carefree Yacht Charters®

Other Destinations

More adventurous families or those with previous charter experience might consider other Caribbean destinations, such as St. Maarten or the Grenadines.

Yacht Styles

Enjoy the islands aboard one of our catamarans and luxury motor yachts. Learn more about our various yacht styles.


Our Caribbean catamaran charters deliver - whether it’s about the yacht, the crew, the watersports, the on-board cuisine or a little bit of everything. Explore the various crewed charter types we offer.