Caribbean Sailing Vacations - Windward Islands

Balmy Trade Winds and Secluded Anchorages

The Windward Islands are for many the favored destination for their Caribbean sailing vacations. The calm trade winds, tropical rainforests, and quiet anchorages make these islands the ideal winter getaway. Set sail on a Martinique catamaran day tour and enjoy an adventure with a French flair, or go sailing St Vincent and the Grenadines and have fun hopping from island to island. A Grenada yacht charter is a great nautical experience both for beginners and experienced skippers. Read more below!

Rodney Bay Marina

Grenada Yacht Club

Saint Vincent

Le Marin

St. Vincent

Martinique Catamaran Day Tour - Diving

Martinique-Catamaran-Day-Tour
Martinique - an alluring mix of French culture with iconic beaches and tropical natural wonders - is a must on your list of Caribbean sailing vacations. Go for a Martinique catamaran day tour from Le Marin, the yachting capital of the island, to explore some of the most amazing diving sites around. Snorkel the scenic Anses d'Arlet to see the green sea turtles, and continue south to the legendary Diamond Rock. The impressive volcanic rock offers a unique experience - you can dive under it!

    Suggested Boats

  • Set sail in Martinique onboard Dufour 44
    $2,658

    Set sail in Martinique onboard Dufour 44
    Le Marin

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  • Set sail in Martinique onboard Dufour  460 Grand Large Liberty
    $3,360

    Set sail in Martinique onboard Dufour 460 Grand Large Liberty
    Le Marin

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  • Set sail in Martinique onboard  this elegant sailing boat
    $8,700

    Set sail in Martinique onboard this elegant sailing boat
    Le Marin

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Sailing St Vincent and the Grenadines

sailing-st-vincent-the-grenadines
Sailing St Vincent and the Grenadines is a thrilling experience for beginners and experienced sailors alike. Let the trade winds guide you along the lush coast dotted with secluded coves and lagoons with turquoise seas and powder white sand beaches. Drop anchor and relax, or go for a swim. Whether you go for a day trip or a week-long charter, sailing St Vincent and the Grenadines is your chance to make your Caribbean sailing vacations unforgettable aboard one of Sailo’s beautiful yachts!

    Suggested Boats

  • Experience Saint Vincent on board this stunning Dufour 405
    $2,268

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

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  • Indulge in the luxury in the Caribbean onboard Ts 42
    $4,050

    Indulge in the luxury in the Caribbean onboard Ts 42
    Le Marin

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  • Explore the Caribbean onboard Lagoon 450 Owner Version Luxe
    $7,296

    Explore the Caribbean onboard Lagoon 450 Owner Version Luxe
    Blue Lagoon

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St Lucia to Martinique Day Trip

St-Lucia-to-Martinique-Day-Trip
Your week-long yacht charter from St Lucia is perfect for a day sail to the cosmopolitan neighboring island of Martinique. Hop aboard your Sailo boat and set sail in the morning, heading to the historic Diamond Rock. Stop for lunch and snorkeling in one of the secluded, lovely bays. Continue your St Lucia to Martinique day trip onwards to the vibrant town of Fort de France, or drop anchor for a peaceful overnight in Anses d'Arlet bay.

    Suggested Boats

  • Experience St. Lucia on board this amazing More Boats More 55
    7,000 €

    Experience St. Lucia on board this amazing More Boats More 55
    St. Lucia

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  • Fun in the sun is all you will experience in St. Lucia
    2,250 €

    Fun in the sun is all you will experience in St. Lucia
    St. Lucia

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  • Enjoy St. Lucia in style on our Nautitech Rochefort
    7,320 €

    Enjoy St. Lucia in style on our Nautitech Rochefort
    St. Lucia

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Itinerary Stop - Grenada Yacht Charter

grenada-yacht-charter
Choosing a sailing itinerary in the Windward Islands can be daunting since the entire region is a tropical nautical paradise waiting to be discovered. If you plan to go sailing St Vincent and the Grenadines, don’t miss your chance to visit Grenada. A yacht charter from Sailo is your ticket to explore the verdant “spice island of the Caribbean”, bordered by stunning unspoiled white and black beaches. Hop off your Grenada yacht charter and enjoy sightseeing, shopping, or exploring historic sites.

    Suggested Boats

  • Explore the picturesque views of Grenada onboard Leopard 384
    $499

    Explore the picturesque views of Grenada onboard Leopard 384
    True Blue

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  • Explore Grenada onboard newest and most luxurious catamataran
    $4,656

    Explore Grenada onboard newest and most luxurious catamataran
    St. George’S

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  • Charter in Grenada and the Grenadines
    $1,099

    Charter in Grenada and the Grenadines
    St Georges

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