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Nautilus Yachting > Yacht Charter > Caribbean Yacht Charter

Caribbean Sailing Holidays

Anchor off your own white sandy beach. Dive into warm turquoise seas to snorkel among the rainbow colours of a coral reef. Relax with a rum punch sundowner on the deck of your yacht while you watch another glorious sunset....

Click on the cruising areas below for more details on sailing in the Caribbean. 

Antigua

Antigua

With 365 palm-fringed beaches and numerous anchorages, Antigua offers excellent sailing round the island. As part of the Leeward Islands, Antigua boasts a spectacular choice of picturesque coves and bays, with fine sand, blue seas and some of the best watersports in the Caribbean.

Bahamas

Bahamas

Cruise the "out islands" of the Abacos, just 1 hour flying time from Miami, an archipelago of pale sandy islands, tranquil bays, sheltered harbours and sleepy historic villages. The beaches are spectacular, mile after mile of white sand and plenty of reefs for fantastic snorkelling and scuba diving.

Belize

Belize

Belize is located on the Caribbean coast of Central America, South of Mexico. Home to the second longest barrier reef in the world, Belize offers superb calm water sailing, diving and snorkelling, Mayan ruins and more - truly an unspoilt holiday getaway.

British Virgin Islands

British Virgin Islands

Come and see for yourself why the BVI is the most popular cruising area in the Caribbean. Perfect sailing conditions and sheltered passages round the islands make this area a delight for all levels of sailors wanting to relax in a Caribbean paradise. Great choice for a first Caribbean charter.

Grenadines

Grenadines

Explore these Robinson Crusoe islands with soft white sand, turquoise seas and spectacular coral reefs. The Grenadines are undeveloped and unspoilt. Nightlife is conspicuous by its absence, peace and solitude are unsurpassed, and the dress code - like the lifestyle - ranges from informal to barefoot casual.

Guadeloupe

Guadeloupe

Cruise around this butterfly-shaped island with a French Creole flavour or sail to neighbouring Antigua. On Guadeloupe the beaches are secluded and the smell of fresh croissants and pastries mixes everywhere with the spicy aromas of West Indian cooking in restaurants and charming bistros.

Martinique

Martinique

Martinique is more relaxed than the Caribbean islands to the north and more sophisticated than the islands to the south. The French influence ensures excellent restaurants. Spend a whole week exploring Martinique or head north to undiscovered Dominica or south to St Lucia.

St Martin

St Martin

This surprisingly little island embodies a dual personality - half French, half Dutch. St. Martin/St. Maarten and the surrounding islands of Anguilla and St Barths offer some of the most spectacular sailing in the Caribbean. Experience beautiful anchorages, stunning sunsets and outstanding restaurants.

Useful Information

The Caribbean is a haven for sailors and those looking for a memorable yacht charter sailing holiday. With so many destinations to choose from, there is something for everyone in the Caribbean. Whether you are an experienced sailor looking for an exciting new adventure or a novice sailor venturing to the Caribbean for the first time, there is a perfect Caribbean sailing destination for you.

The British Virgin Islands

Our most popular sailing area in the Caribbean is the beautiful British Virgin Islands. An idyllic sailing area with over 60 islands and islets to discover. Our clients love the relaxed, friendly atmosphere, calm sailing conditions and the array of excellent snorkel and dive sites. Enjoy paddle boarding and scenic hikes on Tortola, visit the infamous Baths on Virgin Gorda, soak up the relaxed Caribbean vibes at the Soggy Dollar Bar on Jost Van Dyke and snorkel amongst colourful fish on Anegada before enjoying the most delicious lobster dinner.

Antigua

Discover the 365 beaches of Antigua! An island full of naval history and for good reason. Protected by an almost unbroken wall of coral reef, Antigua’s coastline is dotted with safe harbours and anchorages in which to hide away. Stunning beaches can be found at every turn and the world-famous trade winds provide fantastic sailors for experienced and more novice sailors alike.

St Vincent and the Grenadines

One-way charters are incredibly popular in this area and give our clients the opportunity to sail from St Vincent to Grenada or vice versa, enabling you to see as much of the sailing area as possible. One of the great yacht cruising areas in the world, these beautiful, unspoilt islands each have a unique character, from the spice island of Grenada in the south to St Vincent in the north. Visit the islands of Carriacou, Union, Bequia, Mustique, Mayreau and Canouan and anchor in the fabulous Tobago Cays to experience the outstanding snorkelling and diving.

St Martin

For pure escapism, head to St Martin and the surrounding islands of Anguilla and St Barts. Laidback luxury is the order of the day here and the thriving arts and culture scene ensures there will never be a dull moment.

Martinique

Retreat to the fine sandy beaches and lush rain forests of Martinique this winter. Rivers and waterfalls are waiting to be explored and the local cuisine is excellent! French influenced cafes, boulangeries and bistros sit alongside fantastic Creole restaurants - you will not go hungry in Martinique!

Guadeloupe

Are you looking for explore a lesser known area of the Caribbean? Guadeloupe could be just what you are looking for. Discover the palm fringed beaches, colourful coastal towns and ragged cliffs of Grand Terre, then sail over to the luscious green haven of Basse Terre with its rolling mountains, hot springs, mud pools, waterfalls and active volcano!

Belize

For lovers of snorkelling and scuba diving, Belize is hard to beat. With the second longest barrier reef in the world, the underwater world here is in a class of its own. Explore the 175 cayes in this unspoilt sailing area. Belize is a perfect destination to combine your sailing holiday with time spent on land visiting Mayan ruins and dense rain forests.

The Bahamas

Why not visit the iconic turquoise waters and sparkling white sands of the Bahamas this winter? With access to over 200kms of truly idyllic sailing ground, you have plenty of choice for places to visit on your sailing holiday. The Exuma Cays Land and Sea Park is home to an abundance of wildlife species both under the water and on land. Be sure to sample the delicious conch fritters and local rum cake.

The Caribbean Islands see warm temperatures year-round averaging 28-31ºC throughout the year. 

The hottest months

The hottest months are August and September when the waters are at their warmest.

Hurricanes

It should be noted it is hurricane season between June and October.

The wettest months

The wettest and most humid months are September and October.

The best time to sail in the Caribbean is from November to June.

Temperatures stay pretty consistent year-round, averaging 28-32oC with the majority of the rain falling between July and the end of October.

Steady trade winds blow at 15-25 knots during the peak months of December to April, lightening slightly between June and November.

The cost of your yacht charter depends on several factors:

Boat Type

The type and size of the yacht you book will dictate the price. A 1 week charter on a 2 - 3 cabin monohull starts around £1400 in low season whereas a 1 week charter on a luxury catamaran with a skipper in high season could be upwards of £10,000. These are the 2 extremes of the scale for a 1 week charter and we offer plenty of choices in between.

Charter duration

1 week is a popular choice amongst our sailors and makes the perfect short Caribbean getaway. However, to make the most of your time sailing the Caribbean islands, a 10 day or 2 week yacht charter may be just the thing. We provide custom bareboat bookings which can be tailored to your timescale.

Time of Year

Lower-priced yacht charters are available in the low-season of June to the end of October with prices starting to rise in November before peaking from December to April.

Crew

Don't have any sailing experience? No problem! We offer several skippered and crewed options so you can enjoy the yachting lifestyle without the stress. From a simple skippered yacht to fully crewed options, we can arrange a charter to suit your needs.

The mooring fees in the Caribbean vary depending on your sailing destination. There are very few marinas compared to sailing in the Mediterranean so most nights you are on anchor in a bay with a classic Caribbean white sand and palm tree beach.

In areas such as the British Virgin Islands, many locations have laid buoys which cost around US$30/night and give you a safe mooring within minutes of sailing into the bay.

Although useful to have one, a sailing license, certificate or qualification is not required for a Caribbean yacht charter, however, our partners will need to see a complete sailing resume.

The sailing resume for a Caribbean yacht charter must demonstrate experience as a skipper of a similar type and size (within five feet) of the yacht as the one you are looking to charter. The experience should also be recent and the company will look for experience within the last five years. 

A 1 - 2 week charter will give you the optimum time to explore the Caribbean islands, from the palm fringed white sandy beaches to the hidden coves and underwater paradise. Our knowledgeable team can assist you with a custom charter to suit your needs.

We have various 1 and 2 week sailing itineraries for bareboat sailing holidays in the Caribbean that have been personally tried and tested by our team.

Caribbean Sailing Itineraries

The Caribbean islands experience warm temperatures year-round, averaging 28-32oC.

The majority of yachts have fans onboard to keep you cool when below deck and the majority of our clients find this to be sufficient.

Some yachts also provide air conditioning. Our experienced team can advise you on which yachts have air conditioning if this is a priority for you.

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Top 10 Destinations for Sailing Holidays in 2025

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We took a look at the destinations which are currently top of the list and have been surprised by a few of the entries! Tried and tested favourites for your yacht charters stand alongside a few newcomers, keeping things interesting and allowing a few lesser-known sailing areas to have their place in the limelight.