Caribbean Sailing Vacations in the Windward Islands

Discover your Caribbean paradise island by boat rental

With the chance to explore a variety of distinct cultures, a Caribbean sailing vacation in the Windward Islands is the perfect way to discover this diverse region. A Sailo boat rental gives you the freedom to find your dream island.

Stretching from the shores of South America across the Caribbean, the Windward Islands are an island chain known for their diversity. Each of these unique islands has it’s very own character, with influences including French, British and Dutch all leaving their mark on the identities of these individual island nations. 

Today, you’ll find proud and welcoming islanders ready to show you some warm Caribbean hospitality, from Barbados to Martinique. A Caribbean sailing vacation on board of your own private yacht charter gives you the freedom to explore each, or any, of the fantastic Windward Islands nations at your own pace. 


The perfect sailing vacation 

Well known for their favorable sailing conditions year round, the Windward Islands are a true maritime playground. On the water, you’ll find spectacular coral reefs to explore by snorkel or scuba, as well as plenty of beautiful anchorages to moor and explore.

On dry land, the Windward Islands feature landscapes from white sandy beaches, to dense tropical forest and simmering volcanoes. There are also plenty of old colonial towns, luxury resorts, hidden bays and excellent cuisine. In short, a sailing vacation in the Windward Islands has something for everyone, from sun worshippers to adventure seekers.


Where to set sail on your boat rental?

The Windward Islands are the collective name for a group of independent island nations, but you can simply set sail from one, and island hop to your heart's content. If you’re arriving into Barbados, St Lucia or Martinique, you’ll find plenty of choice of boat rentals on Sailo.

Whatever your level of sailing experience, you’ll find something to suit your style and your budget with a Sailo yacht charter. If you’re an experienced sailor, choose from a selection of bareboats including catamarans, sailing yachts and motor yachts. 

Or, if you would prefer to put your feet up on deck, you’ll find plenty of captained boat rentals for an unforgettable Caribbean sailing vacation. Take a look at the unbeatable choice of Caribbean boat rentals on Sailo.

Rodney Bay Marina

Grenada Yacht Club

Saint Vincent

Le Marin

St. Vincent



Beautiful Barbados is one of the most popular sailing destinations in the Caribbean. Bridgetown, the island’s vibrant capital, is a traditional port for cruise ships, with a rich cultural heritage and lots of great nightlife and food. It’s also said that Barbados is where rum was invented, so you’ll should expect to sample plenty of the local tipple in the form of a rum punch. Set sail on board your choice of Sailo yacht charter from Barbados for a world class Caribbean sailing vacation.



Unlike many of the Windward Islands, Grenada sailing is still relatively untouched by excessive tourism. If Barbados has all the creature comforts, Grenada is more content to laze in a hammock with a fruit smoothie and watch the world go by. The islands are home to chocolate and sugar cane plantations, with fantastic local produce available to sample across Grenada. Enjoy this tranquil Caribbean haven from the deck of your private Grenada yacht charter on Sailo, and explore truly secluded islands like Carriacou and Petite Martinique at your leisure.

    Suggested Boats

  • Indulge in the luxury onboard Bali 4.3 in Martinique
    $4,656 (per week)

    Indulge in the luxury onboard Bali 4.3 in Martinique
    Le Marine

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  • Explore St. Martin onboard newest and most luxurious catamaran
    $4,656 (per week)

    Explore St. Martin onboard newest and most luxurious catamaran
    St. Martin

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  • Rent Bavaria 42 in Grenada
    $313 (per day)

    Rent Bavaria 42 in Grenada
    True Blue

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If you’re looking for a Caribbean sailing vacation with a French accent, Martinique yacht charter is calling you. This island is actually a department of France, meaning that you'll see the French flag flying high across the island and you’ll need to pay for your supplies with Euros. The coastline is just made for hopping with a private boat rental, with small towns and anchorages dotted around the island. Being part of France, you’ll find that very few people here speak English, so say, ‘Bonjour’ to a whole different Caribbean sailing experience.

    Suggested Boats

  • Indulge in luxury and comfort aboard
    $7,800 (per week)

    Indulge in luxury and comfort aboard

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Officially the Windward Islands begin at Dominica, with this English speaking nation sandwiched by two Francophone islands. The island is covered in tropical rainforest and is home to a number of hot springs found in the hilly interior, including the Boiling Lake - just don’t go swimming in it! There is plenty to see around the coastline of Dominica, and the rugged interior means it’s often best reached with a yacht charter. If you’re starting your trip here, or stopping by as part of a Caribbean sailing vacation, you’re sure to be awestruck by Dominica’s beauty.

Saint Lucia


As one of the most popular hubs for Caribbean — St Lucia sailing vacations is one of the best places to organise your Sailo boat cruise. The island features a diverse landscape, from jungle and jagged mountains jutting from the sea, to luxury beach resorts and white sandy beaches. There is plenty to do both on sea and land, with reefs for diving, and jungles for ziplining and hiking. Although there is a lot to explore with your yacht charter, the island also makes a great spot to explore other islands including Martinique and the Grenadines.

St Vincent & the Grenadines


With 32 islands to explore, St Vincent and the Grenadines yacht charter make a Caribbean sailing vacation all of their own. In fact, you’ll likely find it hard to prise yourself away from the pristine white sand beaches, the jungle hiking trails and the secluded ocean side hotel resorts. St Vincent is the main island, with most of the yacht charters starting from the capital Kingstown. Sailing Grenadines from here, it’s easy to explore this amazing boating place, or head further afield to one of the neighbouring island nations.

    Suggested Boats

  • Indulge in the luxury onboard this splendid Catamaran
    $4,356 (per week)

    Indulge in the luxury onboard this splendid Catamaran
    Blue Lagoon

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  • Experience Saint Vincent on board this stunning Dufour 405
    $387 (per day)

    Experience Saint Vincent on board this stunning Dufour 405
    St. Vincent

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  • Explore St Vincent and the Grenadines on Lucia 40
    $4,356 (per week)

    Explore St Vincent and the Grenadines on Lucia 40
    Blue Lagoon

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