“You Make the Memories, We’ll Make the Arrangements”
Serena - BVI Sailboat Charter with Captain

Sailing in the British Virgin Islands (BVI) during winter (December to February) is a delightful experience. So, if you’re craving winter sunshine, a luxury sailing holiday in the BVI is your ticket to paradise! On a BVI Sailboat Charter with the Captain, you can expect the following:

  • The temperature is just right—not too hot nor too cold—which makes it ideal for exploring the islands.
  • Expect sunny skies, chilly breezes, and a lower likelihood of rain.
  • Consistent trade winds will propel your sailboat to different destinations.
  • Experience a lively nightlife scene.
  • Enjoy scuba diving and snorkeling for memorable experiences.
  • Note the increased charter rates.

Planning to unwind and bask in the beauty of the British Virgin Islands? If you’re new to sailing, consider a crewed yacht charter with a seasoned captain to navigate while you soak up the awe-inspiring sights all around you. The CKIM Group will make the arrangements, leaving you free to make lasting memories.

What is a Sailboat?

A sailboat, also known as a monohull, features a single hull and uses sails to move with wind power. In addition to its functional design, it is aesthetically pleasing, displaying classic woodwork from decks to finishes that evoke elegance on the water.

You can charter it either bareboat or crewed, allowing you to sail independently or have a captain take charge; sometimes, additional crew members are also on board.

Discover the secrets to a perfect sailing adventure—read our Ultimate Guide before chartering your sailboat!

Let’s explore the key differences between a sailboat and a catamaran

Sailboat (Monohull):

  • Designed with a single hull.
  • This boat tilts under sail yet remains responsive during turns.
  • Although the cabins are smaller, they offer a cozy feel.
  • Its narrower profile allows for easy navigation in marinas, providing an advantage during bustling harbor seasons or winter.
  • Additionally, it operates with no fuel consumption.


  • Designed with twin hulls connected by the main bridge deck.
  • It offers stability and reduced tilting, even when under sail.
  • More space, including larger cabins and bathrooms.
  • Easy to maneuver.

Ultimately, your choice depends on whether you prefer the classic elegance of a sailboat or the spacious comfort of a catamaran for your adventure. For more information, read about BVI Catamaran Charter with Captain.

Why Choose a BVI Sailboat Charter with Captain?

Captain Hugh O'Brien and Chef  Vivianne Swietelsky of Serena Yacht Charter

Choosing a crewed sailboat charter transforms your vacation into an extraordinary journey filled with luxury, adventure, and unique experiences. Here’s why:

  • The professional captain is intimately familiar with the BVI waters and its hidden gems. As a result, they can guide you along the best routes and offer an insider’s view of any destination you want to explore.
  • In a crewed sailboat charter, safety is the top priority. Your seasoned captain handles all navigation to ensure a smooth and worry-free voyage.
  • Your captain can create a flexible itinerary that matches your interests, whether you want to explore private beaches, engage in water sports, or visit famous landmarks.
  • With a professional crew, you can enjoy gourmet meals on board and relax in a spotless cabin.

BVI Sailboat Charter With Captain: Planning your itinerary

Sailboat charters offer the freedom to sail amidst the breathtaking waters of the Caribbean, where azure seas and stunning vistas await. In the British Virgin Islands alone, you can explore many islands and cays during a week-long charter. So, where will you begin your adventure?

Embarking on a sailboat charter from the stunning Virgin Gorda with its natural wonder, The Baths, to savoring the famous Painkiller cocktail in Jost Van Dyke promises a fun adventure.

Here are the detailed itineraries that our travel experts tailored just for you:

If the destinations you want to visit are not included in our current list, we are more than happy to create a new arrangement that perfectly aligns with your preferences! For tailor-made experiences, reach out to the travel experts at ILX TRAVEL today.

Choosing the Right Sailboat Charter in the BVI

After learning how a captain can make a difference in your sailboat adventure, it’s time to choose the perfect boat. Your budget naturally plays a role in this decision. Here are the factors that could influence the charter price:

  • Boat size
  • Number of guests
  • Destination
  • Charter duration
  • Time of year (Holiday rates are generally higher than summer rates)
  • Inclusion of water sports equipment

Sun-kissed islands, crystal-clear waters, and endless fun await you on a sailboat charter. Treat yourself to personalized service on a crewed yacht, where our yacht charter brokers expertly match you with the perfect vessel and crew. Consider the following:

SEA PEARL (Four guests, two cabins, two crew)

  • Year built: 2006
  • Builder: Oyster Marine
  • Winter base port: Caribbean
  • Operating area: Leewards, Windwards, and the British Virgin Islands
  • Charter rates, PLUS expenses:
    • Low rate: $10,000 per week
    • High rate: $12,000 per week
  • Christmas / New Year’s rate is $12,000 per week.
    • Christmas: must not end later than December 26th.
    • New Year’s: must not begin earlier than December 28th.

SERENA (Six guests, three cabins, two crew)

  • Year built / refit: 2017 / 2023
  • Builder: Beneteau
  • Winter base port: US Virgin Islands
  • Operating area: Caribbean Virgin Islands (US/BVI)
  • Weekly inclusive rates:
    • Low rate: $16,900 per week
    • High rate: $22,000 per week
  • Christmas / New Year’s rates:
    • Christmas: $22,000 for up to 4 guests & $24,200 for up to 6 guests.
    • New Year’s: $25,300 for up to 6 guests.

TURTLE 4 (Six guests, three cabins, two crew)

  • Year built: 2008
  • Builder: Oyster Marine
  • Winter base port: Caribbean
  • Operating area: Leewards, Windwards, and Caribbean Virgin Islands (US/BVI)
  • Charter rates, PLUS expenses:
    • Low rate: $22,000 per week
    • High rate: $22,000 per week
$16,900 - $22,000 /wk
  • 3 Cabins
  • 63.00 Ft Sail
  • Built: 2017
$22,000 /wk
  • 3 Cabins
  • 65.00 Ft Sail
  • Built: 2008
$12,000 - $14,000 /wk
  • 2 Cabins
  • 55.00 Ft Sail
  • Built: 2006


When is the best time for chartering in the British Virgin Islands?

The British Virgin Islands offer warm temperatures year-round. However, the best months for sailing and kiteboarding are from December to January, when the winds are stronger. For those seeking sun-kissed weather, June to August is the ideal time to visit the islands. If sailing between May and October, it is advisable to check weather forecasts.

How do I book a crewed sailboat yacht charter?

Please consult CKIM Group, a charter company, regarding your plans. Your charter broker will inquire about the following:

  • What is your dream vacation?
  • When would you like to charter?
  • What type of yacht do you want to charter?
  • Where would you like to visit?

Afterward, we will email you quotes for your review. Upon approval, we’ll send you a charter agreement along with preference forms for food and drink on board. Additionally, you may need to purchase travel insurance.

Sign the contract and submit a downpayment to confirm your booking. We’ll send you a summary of your winter voyage and arrange a pre-departure call 7 to 10 days before your trip.

Finally, you’ll meet your captain and crew to kick off the fun! Your feedback after the trip is highly valued.

Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.