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 Monohull Sailboat Right for Your Trip?

A crewed sailboat charter suits travelers who want time under sail aboard a traditional single-hull yacht. Your captain handles the sailing and passage planning, while the agreed crew provides onboard hospitality. This page focuses on choosing a monohull; for a comparison of sailing catamarans, power catamarans, and motor yachts, visit our crewed yacht charter overview.

Start with the sailing experience you want. Would you enjoy a yacht that heels under sail, a cockpit close to the water, and a week shaped around wind conditions? Or does your group prioritize level living spaces, widely separated cabins, and room to spread out? Discuss those preferences before choosing between a monohull and a sailing catamaran.

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

Compare the Guest Cabins and Deck Layout

Ask for the actual guest layout, including which berths are reserved for crew. Check bed dimensions, bathroom arrangements, storage, cockpit seating, companionway steps, handholds, and access to the swimming platform. A yacht’s overall length alone will not tell you whether the layout works for your group.

Discuss How Much Sailing You Want

Tell your broker whether you want relaxed passages, longer days under sail, or opportunities to participate with the captain’s permission. Ask how the yacht sails in typical conditions and how much motoring the proposed route may require. The captain adjusts the plan to the weather and the group’s comfort.

Match the Yacht’s Draft to Your Route

Share the anchorages and island stops you hope to visit, then ask the captain which are practical for that yacht. Draft, available moorings, sea conditions, and shore access can affect where a monohull anchors. Use our BVI itinerary ideas to start the conversation, leaving room for alternatives.

Confirm Crew Services and the Complete Quote

Request written details of the captain and any chef or host, guest capacity, meal plan, drinks, fuel, mooring charges, and other expenses. Ask which items are included and which are paid separately. Compare date-specific proposals before selecting a yacht, then complete the guest preference information and discuss the sailing plan with the crew.

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?

Your written quote sets the inclusions. Confirm the crew, meals, beverages, fuel, mooring fees, and any other expenses for the specific sailboat; crewed charters do not all use the same pricing terms.

Do I need a license to charter a sailboat?

On a fully crewed charter, the professional captain operates the yacht. Guests do not book as the skipper. If you want a bareboat charter instead, ask the operator what experience and qualifications it requires.

How long is a typical sailboat charter?

Seven nights is a useful starting point for planning. Shorter or longer bookings depend on the yacht, season, itinerary, and available dates.

How many guests are allowed onboard?

Check the yacht’s permitted guest capacity and actual guest-cabin layout. Crew berths, different bed sizes, and shared bathrooms can affect how well a sailboat accommodates your group.

Are there hidden costs?

Ask for a clear list of exclusions before booking. Depending on the quote, meals, drinks, fuel, moorings, local charges, and other services may be included or charged separately.

Do I need to tip the crew?

Crew gratuity is discretionary. Discuss customary guidance with your broker before departure and decide the amount at the end of the charter based on your experience.

Can I bring children onboard?

Discuss children’s ages, sleeping arrangements, deck access, and life jackets before selecting a sailboat. Confirm that the yacht and crew can accommodate your family’s needs.

Can I learn sailing during the trip?

Ask in advance whether the captain welcomes guest participation. Informal participation is subject to the captain’s judgment and is not a sailing course or qualification unless specifically arranged.

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.