Best Sailboat Charters in the Caribbean | Book Now!
Tell us about your destination, group size, and what kind of experience you’re looking for. Then, we’ll match you with the best sailboat charters in the Caribbean. Whether you want a romantic monohull or a roomy catamaran, we’ll help you find the ideal charter.
Choosing the right size sailboat depends on how many people are in your group. It also depends on how much space and comfort you want, as well as your sailing experience.
For most Caribbean trips, boats between 40 and 50 feet offer a good mix of comfort and space. Additionally, they’re perfect for couples or small families. However, larger groups or those wanting more luxury might prefer sailboats between 55 and 80 feet. These usually have more cabins, a bigger kitchen, and extra deck space.
If you’re sailing with kids or are new to sailing, catamarans (usually 45 feet and up) are a great option. They’re also more stable and offer extra room to move around.
Popular catamaran models for Caribbean charters include Lagoon, Leopard, Fountaine Pajot, and Bali, known for comfort and performance. For a luxury, eco-friendly option, consider an electric Sunreef catamaran with solar power and silent cruising.
1. One Planet – Sailing in the Caribbean During Winter
Builder: Sunreef Yachts
Cabins: 3 Queens, 1 King
Guests: Up to 8
Crew: 4
Why Choose It: A 100% electric yacht for quiet, eco-friendly sailing. It also has a modern design, spacious areas, and a flybridge with sun loungers, great for families or groups. Moreover, enjoy organic, Michelin-quality meals made with local ingredients.
Highlights: Awarded Multihull of the Year, this yacht features spacious indoor-outdoor lounging areas and a large galley. Also, enjoy fun on the water with a 10ft floating dock, underwater scooters, a wake surfboard, and more.
Notable Features: Named Best in Class (51’–60′) at the 2023 USVI Charter Yacht Show. Additionally, this luxurious sailing catamaran offers a customizable menu and a bar stocked to your preferences. It also features onboard entertainment with a guitar, ukulele, and keyboard.
Available in: BVI, St. Vincent
Best Monohulls in the Caribbean
Beneteau is a popular sailboat charter model in the Caribbean. It’s known for being comfortable, reliable, and easy to sail. These boats are also great for both experienced sailors and beginners, making them a top choice for exploring the islands.
1. Kai – Sailing in the BVI, USVI, SVI, and Across the Caribbean
Builder: Wellington
Cabins: 2 Queens, 1 Twin
Guests: Up to 6
Crew: 2
Highlights:Kai was built in 1983 and fully updated in 2024. As a result, it runs on solar power and has other eco-friendly features. Onboard, you’ll also meet Sam, a friendly dog who loves playing with kids.
Sailing Destinations: Available across most Caribbean bases
Why Choose It: Serena’s smooth sailing and sleek design make it ideal for exploring the calm, clear waters of the BVI and USVI. So, enjoy snorkeling, relaxing on deck, or watching the sunset with a drink in hand.
Highlights:Antillean is a captain-only sailboat that was refitted in 2024. It’s both pet- and kid-friendly, offering full amenities and scuba diving gear for guests to enjoy.
Bareboat Charters: You get the sailboat and basic equipment for sailing and safety. You take care of everything else such as food, fuel, docking fees, and cleaning.
Captain-Only Charters: A captain comes with the boat to do the sailing. You still pay for food, fuel, and other costs separately.
Crewed Charters usually cover:
The boat and full crew (captain, chef, and sometimes a steward)
All meals, snacks, and drinks (sometimes alcohol too)
Water sports such as snorkeling and paddleboarding
Linens, towels, and basic cleaning
Fuel, mooring, and port fees (depending on the package)
How Much Does it Cost to Charter a Sailboat in the Caribbean?
A Captain-Only Sailboat Charter starts at $12,000 per week. It’s a good choice if you want a captain to sail the boat but prefer to plan your meals and schedule. Moreover, the charter does not include food, fuel, or docking fees.
A Crewed Charter offers a more all-inclusive experience. Prices range from $15,000 to over $40,000 per week, depending on the yacht. It includes a full crew, usually a captain and chef. The sailing yacht covers all meals, drinks, and most onboard activities, so you can relax and enjoy your trip.
Note that rates are higher in peak season (Dec–Apr) and lower in summer and fall. Also, discounts may be available for last-minute deals.
Where is the Best Place to Charter in the Caribbean?
The Caribbean has many island groups, and each one offers a unique sailing experience. Here are some of the most popular places for sailboat charters in the Caribbean:
British Virgin Islands (BVI): Calm waters, steady trade winds, and nearby islands make this a top choice for beginners and families.
U.S. Virgin Islands (USVI): Easily accessible from the U.S., with modern marinas and no passport needed for U.S. citizens.
St. Vincent & The Grenadines: Great for those seeking adventure, with quiet anchorages and beautiful, white sand beaches.
St. Martin / Sint Maarten: A great base for visiting nearby islands like Anguilla and St. Barts.
Grenada and the Southern Grenadines: Quieter and less crowded, known for their natural beauty and rich culture.
The best destination depends on what you’re looking for, whether it’s peaceful beaches or great snorkeling spots. You might also prefer lively beach bars or a more remote, adventurous experience.
Sample Itineraries for Caribbean Sailboat Charters
This 7-day BVI sailing itinerary is perfect for beginners, with calm waters and short sail times between islands. Highlights include snorkeling at The Indians and exploring The Baths. You’ll also enjoy lobster in Anegada and beach bars in Jost Van Dyke.
Day 1: Depart from Tortola and spend the night at Norman Island.
Day 2: Snorkel at The Indians, then sail to Peter Island.
Day 3: Discover Salt Island and relax at Cooper Island.
Day 4: Then, visit The Baths on Virgin Gorda and anchor overnight in North Sound.
Day 5: Sail to Anegada and enjoy fresh local lobster.
Day 6: Next, head to Jost Van Dyke for beach bars and paddleboarding.
This 7-day Southern Grenadines itinerary is ideal for those seeking scenic beauty and fewer crowds. Sail from Grenada to remote islands like Union, Mayreau, and the Tobago Cays. Then, make stops at Mustique and Bequia for a truly off-the-beaten-path adventure.
Day 1: Sail from Grenada to Carriacou.
Day 2–3: Cruise through Union Island, Mayreau, and the Tobago Cays.
Day 4: Visit Canouan and the upscale island of Mustique.
Day 5–6: Explore the laid-back charm of Bequia and anchor by quiet beaches.
BVISAIL can also create a personalized itinerary based on your interests, group size, and travel dates. So, let our team design a custom itinerary just for your Caribbean sailboat charter.
Catamaran Hydrotherapy in the BVI
FAQ About Caribbean Sailboat Charters
Are gratuities included?
No. For crewed charters, a gratuity of 10–20% of the total cost is customary, depending on the services.
What should I pack?
Pack light, breathable clothing, swimsuits, reef-safe sunscreen, and non-slip shoes. Bring personal items such as medications, sunglasses, a hat, and a dry bag for water activities. Most importantly, use soft-sided luggage for easy storage on board.
Do I need travel insurance?
We highly recommend purchasing travel insurance for yacht charters. So, look for policies that cover trip interruptions and yacht-specific coverage.
Ready to Sail? Request Your Free Charter Quote
Let us help you plan the Caribbean sailing vacation of a lifetime. Whether you want a romantic escape or an adventurous family vacation, BVISAIL got you covered.
When requesting a quote, it’s helpful to include:
Number of guests and cabins needed
Preferred departure location
Charter type (bareboat, crewed, or captain-only)
Travel dates
Any special interests (e.g., snorkeling, secluded anchorages, beach bars)
Getting a personalized quote will give you the full cost, availability, and best sailboat charter for your Caribbean trip. Surely, one of our charter specialists will get back to you within 24 hours with available options and pricing.
