Thinking about your first sailing vacation? A private sailboat charter in the Caribbean is one of the best ways to explore tropical islands. It’s also a great option even if you’ve never sailed before.
You’ll have your own boat, your own crew, and your own schedule. These boats, known as monohulls, use sails to glide smoothly through the water. They’re perfect for people who want a real sailing experience, but don’t worry — you don’t need any sailing skills. The crew takes care of everything while you relax and enjoy the view.
When booking a private sailboat, you can choose from three types of charters, such as:
| Crewed Charter | Comes with a captain and crew who handle everything so you can fully relax. |
| Skippered Charter | Includes a licensed skipper to sail the boat while you enjoy the trip with your group. |
| Bareboat Charter | You sail the boat yourself — but you’ll need a valid sailing license. |
If you’ve never chartered a sailboat before, the British Virgin Islands are the perfect place to start. With calm waters, steady winds, and short distances between islands, it’s one of the easiest and most beautiful places to sail.
Meet the fleet: ANTILLEAN, SERENA, BODHISATTVA, KAI, SEA PEARL, and EROS. Each one is ready to make your first sailing trip smooth, relaxing, and full of memories.
Antigua is perfect for beginners. With steady winds and calm waters, it’s easy to sail and explore. You’ll find quiet beaches, historic harbors, and friendly coastal towns. With 365 beaches — one for every day of the year — it’s a peaceful and scenic way to start your sailing adventure.
Looking for the right sailing charters? Check out THE DOVE, OPTIMIST, and HYPERION — three standout choices in the Antigua fleet. Each one offers comfort, style, and a smooth sailing experience that’s perfect for beginners.
St. Maarten is a great choice for your first sailing trip. You’ll cruise between French and Dutch islands, enjoy delicious food, and visit nearby spots like Anguilla and St. Barts. In addition, enjoy smooth sailing, stunning views, and a relaxed, European-inspired vibe.
Check out CAP II, FANCY, AURELIUS, and WHISPER, perfect for a comfortable and memorable first-time charter.
If you have romantic notions about sailing, wooden boats, exploring islands, and waking up to amazing meals… this is the way to do it.
The food and drinks were top-notch. Don’t bother eating ashore!
The combination of a beautiful boat, an amazing crew and great meals make for a wonderful vacation.
Not sure what a sailing vacation looks like day to day?
These sample itineraries highlight what’s possible, from BVI island-hopping to hidden Antigua coves. You’ll also get a taste of French-Caribbean charm in St. Maarten. Whether you’re after relaxation, adventure, or a bit of both, there’s a route that’s just right for you.
Private sailboat charters in the Caribbean typically start around $12,000 per week. In the British Virgin Islands (BVI), most yacht charters are all-inclusive. The rate covers meals, drinks, and water toys.
For St. Maarten and Antigua, charters are usually plus expenses, which means you’ll need to handle provisioning. Therefore, you’ll be buying your own food, drinks, and other supplies before you set sail.
Not at all! Most guests choose crewed charters, which include a professional captain and crew.
Typically: the boat, crew, meals, fuel, and water toys. However, a crew gratuity of 15–20% is customary.
6–12 months ahead is ideal, especially for peak season (December–April).
Absolutely. Your captain will work with you to tailor the route based on your interests and weather conditions.
Yes! Many boats offer family packages with safety gear, kid-friendly meals, and activities.
Sailboats vary in size, but most accommodate 4 to 6 guests. Some larger yachts can host up to 10 guests.
The Caribbean sailing season runs from November to July, with peak months between December and April.
Pack light! Bring swimwear, casual clothes, sunscreen, sunglasses, and soft-soled shoes. Most yachts provide towels and basic toiletries.
Some yachts offer shorter trips, but most charters are 7 nights minimum.
BVISAIL makes it simple to plan your dream sailing trip in the Caribbean, whether it’s your first time or you’ve sailed before. We specialize in crewed sailboat charters in the British Virgin Islands, St. Maarten, Antigua, and more.
Here’s how it works:
Contact us at 1-321-777-1707 or complete this form to discuss your vacation plans.
