In this guide, we’ll show you the best Caribbean sailing charters, from sleek monohulls to spacious catamarans, and what makes each one special. With BVISAIL, we will match you with the perfect yacht and crew, and create a custom itinerary just for you.
| Feature | Monohull | Catamaran |
|---|---|---|
| Stability | Leans with wind, more motion | Very stable, less rocking |
| Space | Smaller cabins and deck | More room to relax and move around |
| Comfort | Can roll at anchor | Stays flat and steady |
| Privacy | Cabins close together | Cabins spread out for more privacy |
| Access | Deeper draft, less shallow access | Shallow draft, anchor closer to shore |
| Cost | Usually more affordable | Typically more expensive |
| Best For | Couples, sailing purists | Families, groups, luxury seekers |
The Caribbean’s most breathtaking sailing experiences are waiting, and the best yachts book fast. So, let’s find your dream sailing yacht in the Caribbean and get you out on the water.
So, you’re ready to sail the Caribbean, but should you go with a sailboat or a catamaran? Available as fully crewed or captain-only charters. So pick your vibe, and we’ll help you book your best choice!
This 66-foot Oyster Marine sailing yacht is ideal for both cruising and racing. She offers water sports such as electric Fliteboarding, wingfoiling, kite surfing, and even deep-sea fishing. Now sailing through the Leeward and Windward Islands, she’s perfect for guests who want a mix of relaxation and excitement.
Recent upgrades to her sails, helm, and onboard amenities ensure top performance and comfort. Also, spacious deck seating for up to 6 guests, perfect for dolphin-watching right from the yacht.
Charter Rate: $25,000 + expenses
With space for up to 6 guests, Abide has spacious cabins, two salons, and three dining areas. A crew of six, including a private chef, is on board to take care of everything. Fresh off a major upgrade in 2024, she’s perfect for peaceful escapes to stunning destinations like the Leewards and Windwards.
Inclusive Charter Rate: $90,000 per week
Sailing Yacht Kai had a major upgrade, making every trip more luxurious than ever. From a fresh paint job to new galley features, plus updated solar and generator systems, Kai is ready to impress.
This elegant monohull sleeps up to 6 guests in 3 en-suite cabins, all featuring classic, cozy interiors. Whether you’re looking for comfort or style, Kai delivers both.
She’s based in the U.S. Virgin Islands, but can easily sail to the British Virgin Islands for your charter.
Seasonal Charter Rates (Inclusive, Caribbean Terms):
| Season | 2 Guests | 3 Guests | 4 Guests | 5 Guests | 6 Guests |
|---|---|---|---|---|---|
| Winter 2024/2025 | $16,000 | $17,000 | $18,000 | $19,000 | $20,000 |
| Summer 2025 | $16,000 | $17,000 | $18,000 | $19,000 | $20,000 |
| Winter 2025/2026 | $18,000 | $19,000 | $20,000 | $21,000 | $22,000 |
| Summer 2026 | $18,000 | $19,000 | $20,000 | $21,000 | $22,000 |
A Sunreef 80 luxury catamaran in the BVI and the USVI, launched in summer 2024. With a striking navy blue hull and elegant, light-filled interiors, this yacht offers a refined escape. It accommodates up to 10 adults, or 5 couples and 2 children, across five en-suite cabins.
Mischievous promises comfort and entertainment, with spacious decks and sun loungers. The flybridge features adjustable day beds for lounging. Moreover, a custom beach club enhances the swim platform for easy water access and relaxation. Three ice makers also ensure a steady flow of chilled cocktails, perfect for relaxing under the Caribbean sun.
Seasonal Charter Rates (Inclusive, Caribbean Terms):
| Season | 2 Guests | 3 Guests | 4 Guests | 5 Guests | 6 Guests | 7 Guests | 8 Guests | 9 Guests | 10 Guests | 11 Guests | 12 Guests |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Summer 2025 | $93,000 | $93,000 | $93,000 | $94,000 | $95,000 | $96,000 | $97,000 | $98,000 | $99,000 | $103,000 | $104,000 |
| Winter 2025/26 | $93,000 | $93,000 | $93,000 | $94,000 | $95,000 | $96,000 | $97,000 | $98,000 | $99,000 | $103,000 | $104,000 |
| Summer 2026 | $93,000 | $93,000 | $93,000 | $94,000 | $95,000 | $96,000 | $97,000 | $98,000 | $99,000 | $103,000 | $104,000 |
This Lagoon 65 is a brand-new charter boat, where you can eat, drink, sail, and dive. You can charter the yacht from West End, Tortola, then sail to the British and US Virgin Islands. Visit Virgin Gorda and enjoy snorkeling in some of the most famous spots, such as The Baths.
Seasonal Charter Rates (Inclusive, Caribbean Terms):
| Season | 2 Guests | 3 Guests | 4 Guests | 5 Guests | 6 Guests | 7 Guests | 8 Guests | 9 Guests | 10 Guests |
|---|---|---|---|---|---|---|---|---|---|
| Winter 2025/26 | $61,000 | $62,000 | $63,000 | $64,000 | $65,000 | $66,000 | $67,000 | $68,000 | $69,000 |
| Summer 2026 | $61,000 | $62,000 | $63,000 | $64,000 | $65,000 | $66,000 | $67,000 | $68,000 | $69,000 |
Award-winning 64ft Privilege Series 6 catamaran, chartering in St. Martin, St. Barths, Antigua, and the Grenadines. Sleeps 6 guests in luxury cabins with ensuite baths and A/C. Additionally, enjoy gourmet dining, a flybridge sun lounge, and smooth sailing.
Seasonal Charter Rates (Inclusive, Caribbean Terms):
| Season | 2 Guests | 3 Guests | 4 Guests | 5 Guests | 6 Guests |
|---|---|---|---|---|---|
| Summer 2025 | $40,000 | $41,500 | $43,000 | $44,000 | $45,000 |
| Winter 2025/2026 | $40,000 | $41,500 | $43,000 | $44,000 | $45,000 |
| Summer 2026 | $40,000 | $41,500 | $43,000 | $44,000 | $45,000 |
Best trip ever! Food was amazing. Crew was truly the best I’ve had. So much fun I can’t wait to come back!
From the moment we stepped on deck, we were greeted with warm smiles, champagne and impeccable service. The yacht itself is absolutely gorgeous—spacious, luxurious, and immaculately maintained, offering the perfect blend of comfort and elegance on the water.
If you are looking to sit back and relax and enjoy all that The BVI has to offer then look no further than Charter Kai. My husband and I booked our trip a year out for our 10 year anniversary. Let me just say it was a once in a lifetime experience.
The Caribbean is perfect for sailing, with warm weather, calm seas, and countless islands to explore. Whether you’re a seasoned sailor or new to chartering, it’s a top destination for a relaxing and scenic adventure.
Here’s why chartering in the Caribbean is a top choice:
Explore crewed vs captain-only yacht.
Each Caribbean island offers something special. So, here are the top picks for your memorable sailing vacation:
Prices vary based on yacht size, season, and inclusions. Therefore, expect $15,000–$50,000+ per week.
The best months to sail in the Caribbean are December through April, when the weather is dry, sunny, and winds are steady.
Top Caribbean sailing spots include the British Virgin Islands, St. Vincent & the Grenadines, and St. Martin. These areas offer calm waters, steady winds, and beautiful scenery, perfect for sailing.
A sailboat between 40 to 80 feet is ideal for the Caribbean. It offers enough space for comfort, good performance in trade winds, and easy access to anchorages. Catamarans are especially popular for their stability and roomy layout.
Sailing the Caribbean can take weeks, but many travelers choose a 7-night charter for a relaxing and scenic getaway. These trips usually follow a set itinerary, visiting top spots like the British Virgin Islands or the Grenadines. In addition, there’s plenty of time for sailing, swimming, and exploring along the way.
Not for crewed charters. The crew handles everything.
The best Caribbean sailing charters fill up fast, especially during peak season. So, book your 7-night sailing adventure now and explore stunning islands and create unforgettable memories. Don’t miss your chance!
Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.
