BVISAIL
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BVI Sail Caribbean Yacht Charters

Crewed Sailboat Charters

Monohull sailboats were the primary yacht type when the charter industry started in the 1970s in the Virgin Islands. There are still excellent crewed sailboat charters in the British Virgin Islands and the Caribbean. With two or more crew members, these yachts delight in sailing and experience the wind in your face and seawater spray. There is nothing like sailing windward on a monohull sailboat in a good breeze.

The winds can be pretty intense during the winter, making for excellent sailing in the Caribbean. Sailing in the British Virgin Islands and US Virgin Islands means shorter and more enjoyable cruises. The Leeward and Windward Islands offer more open sea sailing with longer distances between islands.

Best time of the year | Crewed sailboat charters

Experienced sailors will enjoy sailing during the winter months in St. Martin, St. Lucia, and the Grenadines. From St. Lucia, you can sail south to the Grenadines on a one-way basis. Popular drop-off ports are Union Island in St. Vincent, Grenadines, and Grenada.

The selection of crewed sailboat yachts ranges from Jeanneau, Beneteau, Oyster, Perini Navi, Stephens, Irwin, and many other builders.

Charter Pricing

Yacht charter rates start at $15,000/week to the hundreds of thousands, depending on yacht size, destination, season, and what’s included. Virgin Islands yachts usually include meals and drinks. Plus, the accommodations onboard can be functional, very lavish, and well-appointed.

What’s Included in Your Charter?

Private, fully crewed sailboat

Personalized itinerary

All meals and a ship bar (on all-inclusive charters)

Snorkeling gear, paddleboards, and other water toys

Housekeeping and onboard services

Port fees and taxes (varies by yacht)

Not Included: Airfare, crew gratuities, special requests, and select excursions.

Moreover, popular spots like the British Virgin Islands or the Bahamas can be pricier, especially during busy seasons like winter and holidays.

Early Booking Perks: Secure your dream yacht today and take advantage of special discounts and complimentary upgrades.

Understanding these factors can help you choose the right sailboat charter for your budget and needs.

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The Windwards are sailing south from Martinique to St. Lucia, St. Vincent, and the Grenadines and Grenada with its sister islands. Like the Leeward Islands, the sailor can enjoy longer-distance sailing, beautiful beaches, and anchorage. Land activities like hiking, shopping, and fine dining are all possible.

The Caribbean is excellent for crewed sailboat charters. We look forward to discussing possible options with you. Or, if not a sailboat, a Crewed Catamaran Charter.

The British Virgin Islands remain the most popular Caribbean yacht charter destination. However, during 2022 and maybe 2023, there will be fewer large crewed sailboats available due to the BVI regulations.

Many crewed sailboats may not go through the licensing process. They are instead opting to sail to other Caribbean destinations.

Antigua and Barbuda, St. Martin and St. Barths, St. Kitts, and Nevis are other yacht charter destinations. All offer excellent sailing conditions for the sailor.

In addition, St. Martin and St. Barths offer some of the best dining experiences in the Caribbean.

Charter Pricing

Is a Crewed Sailboat Charter Worth It?

Definitely YES! A crewed sailboat charter lets you relax while a professional captain and crew handle everything. Enjoy gourmet meals, personalized service, and a stress-free adventure in stunning destinations.

Whether you seek a romantic getaway, a family adventure, or a group trip, CKIM Group is here to match you with the perfect yacht. Contact us today and set sail on the voyage of a lifetime!

Request Current Crewed Sailboat Options

Share your dates and guest count to start planning. We’ll follow up about your destination, cabin preferences, and budget.

No obligation to book. Advisory services are free.

Discover Your Ideal Sailing Yacht

Wondering if a classic sailing yacht is the right choice for your next adventure? Take our quick quiz and uncover the best yacht style for your group, preferences, and cruising goals.

Take the Sailing Yacht Quiz
Instant results • No obligation • 100% free

Our team will also craft an itinerary based on your interests, ensuring a seamless and memorable journey.

3-Day BVI Sailing Itinerary 7-Day BVI Sailing Itinerary 4-night BVI Sailing Itinerary 4-Day BVI Sailing Itinerary 5-night BVI Sailing Itinerary 5-day BVI Sailing Itinerary 6-Day BVI Sailing Itinerary 7-night BVI Sailing Itinerary 8-Day BVI Sailing Itinerary 10-Nights BVI Sailing Itinerary 10-Day BVI Sailing Itinerary 14-Day BVI Sailing Itinerary 2-Week BVI Sailing Itinerary

Booking Your Crewed Sailboat Charter

Booking in advance ensures the best selection of sailboats and destinations. Many top-tier yachts fill up months ahead, especially during peak travel seasons.

How to Charter a Sailboat with BVISAIL

Step‑by‑Step Process

  1. Define your sailboat charter goals

    A. Share your details with BVISAIL:
    Preferred charter dates
    Destination, including BVI, USVI, Bahamas, or wider Caribbean
    Special occasions, such as a honeymoon, anniversary, or corporate retreat
    Interests and activities, such as diving, island-hopping, and cultural tours
    B. Who will be traveling with you?
    Family
    Friends
    Business associates
    C. What’s your sailboat charter budget range?
    $150,000+ per week plus expenses
    $100,000+
    $75,000+
    $50,000+
    $35,000+
    D. What type of sailing yacht do you prefer?
    Sailing Catamaran
    Sailboat
    E. What’s your group’s charter history?
    Tip: Book at least 9–12 months in advance to secure the best sailboats and destinations. This is one of the reasons why chartering with a U.S.-based brokerage helps you plan with confidence.

  2. Schedule an appointment with BVISAIL

    Discuss preferences with a BVISAIL charter expert. Then, we’ll review destination options, yacht types, and finally recommend travel insurance.

  3. Receive your yacht charter proposal

    Tailored proposal with sample itineraries, rates, and testimonials.

  4. Select your yacht

    To begin, review the proposal. Then, select your yacht. Afterward, talk through upgrades or excursions.

  5. Finalize contracts and confirmations

    Review agreements, hold dates, and make payments securely.

  6. Prepare for your trip

    Start by completing preference forms. After that, schedule a captain’s call. In the end, review your itinerary.

  7. Pre-departure call

    7–10 days before departure, review final details with your group.

  8. Embarkation

    Finally, board the yacht, meet the crew, and begin your charter.

  9. During your trip

    The crew provides daily briefings and support.

  10. Disembarkation

    Final settlements, farewell to crew.

  11. Post-trip

    Afterward, a feedback survey and follow‑up call help plan future charters.

Why Book With BVISAIL’s Charter Brokers?

Because trusted expertise turns a good yacht trip into an unforgettable one.

More than 20 years of combined yacht and travel experience Independent comparisons across multiple fleets Firsthand yacht and crew knowledge No additional broker fee Planning support before, during, and after the charter

Frequently Asked Questions

What is included in the charter fee?

The sailboat, crew, food, drinks, and basic equipment.

Do I need a license to charter a sailboat?

Yes, for bareboat charters. No, for crewed charters.

How long is a typical sailboat charter?

Usually one week, but shorter trips are possible.

How many guests are allowed onboard?

Most sailboats are limited to up to 8 guests.

Are there hidden costs?

Yes, expect port fees, fuel, food, and sometimes VAT.

Do I need to tip the crew?

Yes, 15–20% of the charter fee is customary.

Can I bring children onboard?

Yes, most sailboats welcome families.

Can I learn sailing during the trip?

Yes, crews often teach guests.

Explore Yacht Charter Quizzes

Find your perfect yacht style, travel vibe, and charter experience.

Yacht Match Quiz Catamaran Charter Quiz Sailing Yacht Quiz Power Yacht Charter Quiz Couples Yacht Quiz

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