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Caribbean Yacht Charter & Sailing Holiday

On a Caribbean sailing holiday, you’ll experience your nautical dreams in a unique and thrilling way. Set sail aboard your private charter yacht from one of seven island bases, each with its own distinct history, delicious cuisine, and culture waiting to be discovered. 

Whether you want calm, protected waters and short island hops or exhilarating blue water passages, the Caribbean is one of the most exciting sailing holidays 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 harbour to the next aboard your own monohull or catamaran Caribbean charter.



  • Sheltered sailing within a barrier reef
  • Consistent coastal trade winds to exploit
  • Incredible rainforests and Mayan ruins

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Where is the best place to sail in the Caribbean?

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 everyday.

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 BVI

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.

What are the best things to do in the Caribbean?

Feel your cares melt away as you embark on a magical Caribbean charter, following a carefully curated itinerary.

Whether you book a relaxing BVI yacht charter, a sensational holiday in Antigua, or 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:


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.


One of the best things to do in the Caribbean is experience the wonders of snorkelling and scuba diving. If you’re visiting the Bahamas, diving around the blue holes to the northwest of Little Harbour is an unforgettable experience.


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?


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.


The perfect destination for water lovers, enjoy world-class fishing in Belize before snorkelling around the world’s second-biggest barrier reef. How much marine life can you spot?


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.

When is the best time to visit the Caribbean?

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 BVI, and other sailing spots in the Caribbean.

Avoid the hurricane season between May 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 goodbye to the dark nights and stormy UK weather and hello to a cloudless paradise, complete with picture-perfect beaches, warm evenings, and breathtakingly blue waters.

What are the sailing conditions in the Caribbean like?

Many of our Caribbean destinations, such as the BVI, 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 24-32 degrees Celsius 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.

How much do Caribbean yacht charters cost?

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:

  • Which of our destinations you book
  • Whether you choose a bareboat, skippered, or flotilla sailing charter
  • Your Caribbean yacht charter cost will differ depending on the duration of your relaxing trip
  • Which of our incredible catamarans or monohulls you climb aboard
  • How many excursions you plan on doing
  • What time of year you visit the Caribbean
  • Extras

Design your dream Caribbean sailing holiday today by choosing the destination you want to set sail around and building a quote.

How much are the moorings fees in the Caribbean?

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 (GBP 3.50-4.50) per foot.

If you want to moor up and explore one of the Caribbean’s breathtaking islands, you will pay around XCD 67.00-81.00 (GBP 20.00-24.50).

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

How long does it take to sail the Caribbean?

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 holiday can be as long or as short 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 holiday 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, snorkelling, cultural attractions, thrilling activities, exploring hidden islands, and relaxing on golden sands, you may want a two-week holiday instead.

Many of our Caribbean 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 itineraries:

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