Caribbean Sailing Vacations

Caribbean Sailing Vacations was born from encounters with clear, turquoise waters, the warmth of the sun, sunbathing on white sand beaches and the feel of a cool ocean breeze.

We invite you to join us on one of our private, crewed yachts – the ideal companion for your sailing adventure.  While each boat and crew has its own personality, our private fleet shares a modern, classy style, providing you with warm hospitality and a safe, comfortable environment to sail.

Caribbean Sailing Vacations is committed to our guests, owners and crews.  We meticulously care about our guests experience reflecting our quest for excellence – ensuring the highest standard of customer service.

Yacht Types

Caribbean Sailing Destinations

BVIThe British Virgin Islands, situated to the east of Puerto Rico and the US Virgin Islands and north-west of Anguilla. Offering an abundance of famously picturesque white sandy beaches, crystal clear waters and tropical weather conditions. The Islands themselves are made up of four main islands; Tortola, Virgin Gorda, Anegada and Jost Van Dyke including over fifty other smaller islands and around sixteen uninhabited gems! The British Virgin Islands boasts steady trade winds, calm currents, protected bays and line of sight navigation which makes the BVI the sailing capital of the world!

Throughout the BVI you’ll find sheltered harbours, stunning beaches, fresh seafood and a variety of awesome diving and snorkelling spots (to name only a few). There is never a dull moment around the islands and each island has its very own unique character. The list is endless as to why the British Virgin Islands are known as the number one sailing destination! The British Virgin Islands makes for an exceptional sailing charter destination. Contact Caribbean Sailing Vacations today for further information.


Antigua is located in the West Indies and makes up part of the Leeward Islands where you can experience the world famous trade winds, providing unlimited, ideal sailing conditions for sailors of all levels of experience. Follow the island’s winding coastline and you’ll be sure to find an array of hidden coves and small bays which are great for exploring and when you venture underwater, you’ll find an impressive protective coral reef hosting a variety of marine life for you to discover whilst snorkelling or scuba diving.
Antigua is vibrant and packed full of history, offering not only great sailing holiday conditions out on the water but an opportunity to walk in the same footsteps as Christopher Colombus whilst on land amongst several other sites not to miss such as historical forts and ancient monuments. Embrace the delights of Antigua on your sailing charter and contact Caribbean Sailing Vacations today for further information.

St Martin

St Martin, the second most popular sailing charter destination in the Caribbean following the British Virgin Islands. St Martin forms part of the Leeward islands and offers a very unique, dual culture, Caribbean Island experience with an array of European delights to enjoy. The island comprises two separate countries, the north, being the French side, Saint Martin and it’s southern Dutch side, Sint Maarten.

The island is home to world famous, renowned beaches and hidden coves. Chartering in St Martin allows you to explore a selection of some of the most unspoilt reefs in the world whilst snorkeling or diving. World class Caribbean / European fusion cuisine, vibrant nightlife, captivating colonial history, relaxed beach bars and stunning beaches make a fantastic concoction for a St Martin yacht charter. Grasp the fusion of St Martin on your sailing charter and contact Caribbean Sailing Vacations today for further information.


Guadeloupe is a French overseas region that is part of the Leeward Islands, forming an island group within the southern Caribbean sea. Guadeloupe was discovered by Christopher Columbus the explorer in 1493 and has a charming island resemblance to the shape of a butterfly. It’s two largest islands are separated by the Salee River. Hilly Grande-Terre Island is home to Pointe-a-Pitre, the islands biggest city and Basse-Terre Island is less developed and dominated by a stunning national park.

The French influence is unmistakable and the mouth-watering smell of fresh pastries alongside the powerful smell of Caribbean spices makes for an intriguing collaboration. The island is covered in tropical forests boasting banana, pineapple and sugarcane plantations. Not to forget several beautiful waterfalls and refreshing natural pools to enjoy. Nearby Marie Galante boasts fantastic snorkelling and the Gosier islet and it’s impressive reef – make sure you include both visits during your Guadeloupe sailing charter.
Make Guadeloupe your sailing destination and contact Caribbean Sailing Vacations for more information.

Martinique forms part of the Windward Islands, located directly north of St Lucia in the Lesser Antilles of the West Indies in the eastern Caribbean sea. Like Guadeloupe, Martinique is a French overseas region the capital, Forte-de-France, is the pinnacle of sophistication combining art galleries, shops, museums and theatres all for your enjoyment. On top of the islands tropical climate and desirable cruising conditions, Martinique offers an array of flawless beaches and you’ll be spoilt for choice with the white sand in the south and black volcanic sand in the north. Martinique offers quaint fishing villages, natural hot springs, luscious green rainforest and scenic mountain tops to explore on land, as well as glorious reefs and marine life to discover underwater.
You also have the option to island hop between Petite Anse d’Arlet and St Pierre or head to Bequia, St Lucia’s Rodney Bay and the Soufriere’s waterfalls, volcanoes and hot springs whilst you experience a Martinique sailing charter. Relish in the rewards of a Martinique yacht charter and contact Caribbean Sailing Vacations today to find out more information.

St Vincent and The GrenadinesSt Vincent and The Grenadines consists of the main island, St Vincent, as well as the northern two thirds of the Grenadines to the south of St Vincent. Forming part of the Windward Islands with 32 islands and cays to explore, a fraction of which are inhabited, it is the very definition of tropical paradise.
The stunning Tobago Cays are located in the Grenadines and should be at the very top of your must see list! Home to classic Caribbean white beaches, coconut palm trees, deliciously warm weather, clear visibility waters with reefs to delve into and the perfect trade winds for the ultimate sailing experience, no wonder it’s a true hotspot for a sailing charter holiday. Regardless of where you sail, you’ll flourish in a Caribbean dream vacation as each island has its own distinctive enticement and characteristic. Experience your once in a lifetime sailing trip to St Vincent and The Grenadines. Contact Caribbean Sailing Vacations today for more information.

GrenadaGrenada is located at the southern end of the Grenadines and is also known as the ‘Spice Isle’ of the Caribbean. The hilly mainland is home to numerous nutmeg, cinamon, clove, ginger and allspice plantations, the famous kaleidoscope of colourful houses, exotic flowers and rare fruits. Grenada is the ideal gateway to the perfect and unspoiled sailing location of the Grenadines.

Catch the wind in your sails and heighten your senses whilst sailing in the Grenadines with a spectacular combination of blue water cruising and consistent trade winds, you can explore Grenada’s 45 postcard-perfect beaches including the 1.9 mile-long Grand Anse beach in St George Paris, which frequently appears in the top 10 lists of the world’s greatest beaches. Be sure to take advantage of the irresistible snorkeling and scuba diving spots and easy island hops to neighbouring Carriacou, Petite Martinique and St Vincents, you’ll have an abundance of adventure right at your fingertips! Savor every moment of your sailing charter in Grenada and contact Caribbean Sailing Vacations now to start planning.

St LuciaSt Lucia is an eastern Caribbean island situated in the West Indies on the boundary of the Atlantic Ocean. The island’s coast is home to magical volcanic beaches, dazzling reef diving and snorkelling sites and charming fishing villages. On land, trails through the luscious rainforest lead to breathtaking waterfalls such as the 15m high Toraille, St Lucia truly is an island paradise for water lovers.

St Lucia is the jewel of the Windwards islands, regardless of which side of the island you are enjoying, St Lucia offers superb sailing conditions with year-round sun and varied seasonal winds. You can sail to St Vincent and the Grenadines in the open water passages whilst taking it easy with line-of-sight navigation. Spend your mornings lounging on the luxurious powder-white sands and snorkelling the warm, shallow waters. Enjoy all of the delights of St Lucia on your sailing charter and contact Caribbean Sailing Vacations for more information today.

St Martin
St Martin

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Caribbean  Sailing Vacations