Turquoise waters, steady trade winds and tranquil cays
Sailing in the Caribbean. On a Caribbean sailing vacation you can swap fix-it weekends for charting your own course. On our award-winning yachts you’ll experience your nautical dreams in a unique and thrilling way. Set sail aboard your private charter yacht from one of eight premier bases, each with their distinct history, delicious cuisine and culture waiting to be discovered. The British Virgin Islands, the Bahamas, St. Martin, Antigua, Grenada, Martinique, St. Lucia, and Belize await.
Whether you want calm, protected waters and short island hops or exhilarating blue water passages, the Caribbean is one of the most exciting sailing vacations you can experience.
More than 5,000 islands, reefs and cays make the Caribbean a picture-perfect paradise for sailors at any experience level. You’ll enjoy easy line-of-sight navigation, deep water passages and lively island-hopping from one charming harbor to the next aboard your own monohull or catamaran Caribbean charter.
All aspects of trip from booking, to asking questions, to checking in and checking out went very smoothly. We’ll be back before long.
The whole process is smooth from the start to the finish. All staff are very friendly and helpful. Loved the Catamaran and all the facilities on board.
I have chartered with Sunsail many times, in many destinations. The boats are very clean and in good shape and the base crews are friendly and helpful.
From start to finish, the Sunsail owner and staff were welcoming, extremely competent, informative and professional. We can’t wait to go back. The boat was in excellent condition and the check-out and sailing guides made our family vacation the best it could be
We had an overall good experience with our charter. The staff were friendly and helpful, the boat was in mostly great shape and the vacation was wonderful!
Sunsail has always provided an excellent charter experience for us. We appreciate the product this company provides, and the effort to create a reliable, high-quality sailing vacation.
Boat was in excellent condition. Staff were very friendly, knowledgeable, and professional.
Fantastic customer experience. The staff are polite and patient. They take time to explain the boat and answer questions.
They even sat down to review our sailing itinerary and made suggestions based on local weather and sailing experience to ensure we started our week off right!
Save 10% on your adventure in Bahamas! Book by 1 March 2026. Terms and conditions apply.
Book your charter early and explore breathtaking destinations around the globe –save 10%! Book by March 1st, 2026.
Frequently asked questions
The Caribbean is a treasure trove of wonders, with secluded islands and hidden coves to explore around every corner. With so many incredible places to visit, you could sail around the Caribbean for eternity, and still find something new every day.
But where is the best place to sail in the Caribbean?
For New to Sailing
With line-of-sight navigation and smooth sailing conditions, beginner sailors will love the enchanting British Virgin Islands.
For Couples
The romantic beach settings of St Lucia are the ideal honeymoon destinations for loved-up couples.
For Adventure
For the underwater adventurers among you, Belize is known as one of the best places in the world for scuba diving.
For Culture
Are you looking for a Caribbean island steeped in history and culture? Book a sensational sailing charter in Martinique.
For Foodies
For food and drink lovers, Grenada’s famous spices and rum are second to none. If you want to immerse yourself in the laid-back island lifestyle.
For Beaches
St Martin’s gorgeous beaches are perfect for soaking up the sun. Speaking of incredible beaches, Antigua is home to 365 of them, each one unique and equally breathtaking.
Feel your cares melt away as you embark on a magical Caribbean charter, following a carefully curated itinerary.
Whether you book a relaxing British Virgin Islands yacht charter, a sensational vacation in Antigua, or a majestic sailing charter in the Bahamas, your itinerary will take you to the best beaches, islands, and secluded anchorages the Caribbean has to offer.
Take a look at some of the best things to do in the Caribbean; it may even help you decide which of our beautiful destinations to choose:
Antigua
Moor up and enjoy an on-shore adventure as you hike around one of the many trails of Antigua’s stunning hills. With its combination of luscious green spaces and golden sands, you’ll never be short of incredible views.
Bahamas
One of the best things to do in the Caribbean is to experience the wonders of snorkeling and scuba diving. If you’re visiting the Bahamas, diving around the blue holes to the northwest of Little Harbour is an unforgettable experience.
Grenada
Soak up the sun on the heavenly beaches of Grenada. Will you sunbathe on the golden sands of Grand Anse Beach, swim in the crystal-clear waters surrounding Morne Rouge, or seek shade under a palm tree at Magazine Beach?
British Virgin Islands
Island hop around the BVI and immerse yourself in the cultures of Tortola, Virgin Gorda, and Jost Van Dyke. Each island offers a unique experience where you can create magical memories as you explore hidden coves, stunning beaches, local towns, and beautiful restaurants.
St. Lucia
One of the most romantic destinations in the entire world, fall in love with the natural beauty of St. Lucia, with its enchanting waterfalls, thermal pools, and turtle sanctuary.
St. Martin
Are you looking for the best things to do in the Caribbean as a couple? Chase the romantic sunsets in St. Martin, some of the most beautiful in the world.
Belize
The perfect destination for water lovers, enjoy world-class fishing in Belize before snorkeling around the world’s second-biggest barrier reef. How much marine life can you spot?
Martinique
Enjoy the delicious cuisine of Martinique, a unique French-Caribbean blend. If you want to try a traditional dish, we love Colombo de Martinique. It’s an aromatic, flavoursome stew made with lamb, coconut milk, and ginger.
One of the most common questions we get asked is, When is the best time to visit the Caribbean? You want beautiful weather, incredible sailing conditions, and not too many tourists, and we want that for you, too.
The best time to visit the Caribbean is between December and April. This time of year is also known as ‘sailing season’, which means you’ll find plenty of thrilling regattas and races to enter in Antigua, the British Virgin Islands, and other sailing spots in the Caribbean.
Avoid the hurricane season between June and November if you want to steer clear of wetter and windier conditions.
The Caribbean is the ultimate winter sun destination, making it the perfect escape in the New Year. Say hello to a cloudless paradise, complete with picture-perfect beaches, warm evenings, and breathtakingly blue waters.
Many of our Caribbean destinations, such as the British Virgin Islands, enjoy year-round sailing conditions, which make them ideal sailing destinations, no matter when you decide to book a yacht charter.
During the wet season (May-November), you may experience higher humidity and rainfall, whereas the dry season is cooler and drier. The beautiful islands of the Caribbean still enjoy sizzling temperatures of between 75-90 degrees Fahrenheit all year round.
The tidal range in the Caribbean is very small, which makes it a wonderful sailing destination for first-time sailors!
The sailing conditions in the Caribbean will differ slightly depending on where you’re sailing. Take a look at the ‘sailing conditions’ tab in each of our Caribbean destinations to find out more.
As you prepare to take the helm and set sail around the crystal clear waters of the Caribbean Sea, you might be wondering how much a private yacht charter in the Caribbean will cost.
The cost of a charter in the Caribbean depends on a number of factors, including:
Design your dream Caribbean sailing vacation today by choosing the destination you want to set sail around and building a quote.
Docking and mooring fees in the Caribbean will differ depending on your destination, and will also depend on how long you plan on docking or mooring up for.
Docking fees are calculated based on the size of your yacht. On average, you can expect to pay between XCD 8.00-11.00 (USD 2.96-4.07) per foot.
If you want to catch a mooring ball for the night and explore one of the Caribbean’s breathtaking islands, you will pay around $15 to $40 depending on the island and location.
If you have any questions about docking and mooring fees in the Caribbean, our friendly base crew will be available at each of our destinations to offer guidance.
When you book a sailing charter with Sunsail, you can choose one of our world-class destinations to set sail around. This offers you the perfect opportunity to discover the magic of specific Caribbean islands in detail and at your own pace.
Your Caribbean sailing vacation can be as long as you wish. We pride ourselves on delivering bespoke yacht charters, designed to your exact requirements. If you want to enjoy a slow-paced, tranquil vacation with sunbathing and cocktails aplenty, you may decide that one week is long enough. However, if you want to fill your itinerary with scuba diving, snorkeling, cultural attractions, thrilling activities, exploring hidden islands, and relaxing on golden sands, you may want a two-week vacation instead.
Many of our Caribbean sample itineraries are one week long, with plenty of time to explore beautiful islands, off-the-beaten-track beaches, charming local towns, and more.
Take a look at our Caribbean sample itineraries:
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