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Crewed Sailing Holidays in the Caribbean

Private or cabin cruises in the Caribbean, with crew, all-inclusive service, and endless adventure.

Perfect for couples, families, or small groups: spacious, modern catamarans offer the ideal Caribbean holiday for travellers seeking comfort, space, and effortless luxury.

Enjoy gentle ocean breezes as you glide across calm turquoise lagoons and discover quiet anchorages and secluded beaches that are impossible to reach by land. Whether snorkelling among colourful coral reefs, strolling along pristine sandy shores, or sipping a glass of wine while watching the sunset from the deck, a catamaran holiday offers the perfect blend of relaxation and adventure.

With spacious cabins, modern amenities, and a professional crew taking care of every detail, you can fully unwind while exploring charming island villages, spotting playful dolphins, or simply soaking in the serene Caribbean scenery. Every day brings new opportunities to create lasting memories in comfort, style, and adventure.

Getting there

British travellers can reach the Caribbean via direct flights from London to key hubs such as Barbados, Antigua, Saint Lucia, or Saint Vincent, with short transfers to major marinas.

Available Crewed Catamaran Sailing Holidays in the Caribbean

Crystal-Clear Waters, White Sand Beaches, Comfort, and Relaxation

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The top destinations for your sailing vacation in the Caribbean

The Grenadines & Martinique

The Grenadines & Martinique

A string of small, enchanting islands, the Grenadines are famous for crystal-clear waters, vibrant coral reefs, and pristine beaches.

From Bequia’s charming harbors to the untouched Tobago Cays, the islands offer sheltered bays perfect for anchoring. Snorkel among colorful marine life or relax on deck while enjoying breathtaking scenery.

Visitors from London can reach the Grenadines via Saint Vincent (SVD) or Martinique (FDF), followed by short transfers or inter-island flights. Adventure, relaxation, or both await in the Grenadines. 

Find Your Cruise in The Grenadines & Martinique.

Antigua & Barbuda

Antigua & Barbuda

Famous for 365 beaches — one for every day of the year — Antigua & Barbuda is a sailing paradise. Turquoise waters, lush landscapes, and historic forts make it ideal for adventure and relaxation.

Anchor in secluded bays, explore St. John’s, or visit Barbuda’s pink sand beaches and pristine reefs. Visitors from London can fly directly to V.C. Bird International Airport (ANU) and reach major marinas in minutes.

Known for Antigua Sailing Week, the islands offer steady winds, calm anchorages, and welcoming locals

Find Your Antigua & Barbuda Cruise.

BVI – British Virgin Islands

BVI – British Virgin Islands

The BVIs feature rugged coastlines, protected bays, and lush hills ideal for hiking.

Highlights include The Baths on Virgin Gorda, White Bay Beach and Bubbly Pool on Jost Van Dyke, and the RMS Rhone wreck off Salt Island for diving or snorkeling.

Visitors from London usually fly to St. Thomas (STT), then take a short ferry or charter transfer to the BVIs. With perfect sailing conditions and varied anchorages, the BVIs are a top choice for British travelers seeking adventure. 

Find Your BVI Cruise.
 

Bahamas

Bahamas

Just a few miles from Miami, the Bahamas is an archipelago of around 700 islands. Some, like the capital Nassau, are bustling and densely populated, while others, such as many of the Exumas or Abaco Islands, remain wild and uninhabited.

The islands enjoy steady winds year-round, making them a paradise for sailing or catamaran trips. Explore hidden bays, visit Thunderball Cave in the Exumas, admire Dean's Blue Hole on Long Island, or dive the coral reefs around Conception Island.

For those seeking views from above, climb the hills of Waderick Wells Cay and enjoy breathtaking panoramas of the archipelago

Find Your Bahamas Cruise.

Practical info

Territory

The Caribbean is a stunning region of islands in the Caribbean Sea, stretching from the Bahamas and the southern United States down to the northern coast of South America. For British travellers seeking sailing holidays, the most popular destinations include Barbados, Antigua & Barbuda, Saint Lucia, the Grenadines, and the British Virgin Islands, each offering its own unique charm—from pristine beaches and turquoise waters to vibrant local culture and welcoming communities.

Population

The combined population of these islands is over 4 million, with each destination offering a mix of lively towns and peaceful, secluded spots perfect for anchoring.

Documents and currency

For a sailing holiday in the Caribbean, British citizens require a passport valid for at least six months. No visa is generally needed for short tourist stays in Barbados, Antigua & Barbuda, Saint Lucia, the Grenadines, or the BVI.
Currency: Barbados, Antigua, Saint Lucia, the Grenadines, and the BVI primarily use Eastern Caribbean dollars or US dollars, with major services often accepting credit cards.

Language

English is spoken throughout these islands, making communication straightforward for UK travellers. In French-speaking territories such as Martinique, basic phrases in French can enhance your experience.

Getting There 

Travellers can reach these sailing hubs via direct flights from London to key airports such as Grantley Adams International (BGI, Barbados), V.C. Bird International (ANU, Antigua), Hewanorra International (UVF, Saint Lucia), and Saint Vincent (SVD). Short transfers bring you to the main marinas and charter bases, allowing for a smooth start to your sailing holiday.

Getting around 

Most airports are conveniently located near the main ports of embarkation. Once aboard your catamaran, the skipper takes care of navigation, guiding you to the most beautiful islands, bays, and hidden beaches—no additional transport is needed.

Cellular network

You can stay connected using your UK mobile provider’s international roaming, but a more cost-effective option is to purchase a local or virtual SIM card with a set amount of data and minutes. This ensures easy access to maps, weather updates, and communication while at sea.

FAQ

Guides & tips

The Caribbean archipelago by sailboat

Where to travel

The Caribbean archipelago by sailboat

Grenadines, Martinique, Guadeloupe and St. Martin by sailboat 

Where to travel

Grenadines, Martinique, Guadeloupe and St. Martin by sailboat 

British Virgin Islands by catamaran

Where to travel

British Virgin Islands by catamaran

When to go on a catamaran cruise in the Caribbean

When to travel

When to go on a catamaran cruise in the Caribbean

Antigua and Barbuda by sailboat

Where to travel

Antigua and Barbuda by sailboat

Bahamas by sailboat and catamaran

Where to travel

Bahamas by sailboat and catamaran

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