Island Windjammer Cruises

Sail the Windward Islands with Island Windjammers

The Grenadines are part of the Windward Islands, known around the world as a yachtsmen's paradise. The Grenadines are an exclusive sailing ground made up of over 600 islands, divided between the two nations of Grenada and St. Vincent & the Grenadines. Our captains have designed an itinerary that offers the most desired ports of call in the region.

6 Night Windward Islands Cruises

Home port:
St. George’s, Grenada or Marigot Bay, St Lucia

Visit a selection of:
Bequia, Carriacou, Mayreau, Tobago Cays, Union Island

12 Night Explorer Windward Islands Cruises

Home port:
St. George’s, Grenada or Marigot Bay, St Lucia

Visit a selection of:
Bequia, Canouan, Carriacou (Tyrell Bay), Carriacou (Hillsborough), Grenada, Mayreau, Mustique, Petit St. Vincent, Sandy Island, St. Lucia, St Vincent, Tobago Cays, Union Island, Young Island
Island Windjammers Cruises: Caribbean Sailing Cruise Destinations

Embark: 12:30pm- 2pm / Disembark: No later than 10AM

Bequia

Bequia may be known for its boat building and seafaring heritage, but it’s the seafood pizza at Mac’s that shipmates can’t seem to forget. Be sure to visit the Old Hegg Turtle Sanctuary, but save some time for shopping at tiny boutiques filled with local art, scrimshaw and model boats. A sail, kayak or dive excursion from the white beaches of Bequia completes your visit.

Carriacou

Take a step back in time to the real Caribbean. Known for their boat building and seafaring skills, Carriacou locals can trace their ancestry to Africa and Scotland. Explore the old cemetery, and find centuries-old markers. Feast on fresh-caught lobster in season, or grab a snorkel and take a short swim to the coral reefs, which teem with colorful marine life.

Mayreau

Take a hike through the village to the other side of Mayreau for a refreshing swim in gleaming Saltwhistle Bay, arguably the most beautiful bay in the Caribbean. Be sure to stop at the crest of the hill by the church for a majestic view of Tobago Cays, Canouan and Union Island. The highlight of any visit to Mayreau is the Cultural Walk, a progressive tour of local watering holes that offers an “intoxicating” taste of the local nightlife.

Tobago Cays

Why settle for one perfect uninhabited islet when you can have many? Tobago Cays are what tropical dreams are made of: stretches of unspoiled beaches, water as clear as glass, and “t-shirt trees” that beg you to bring unique home colorful souvenirs. You'll be counting the days until you can return!

Union Island

Volcanic Union Island, the southernmost island of St Vincent and the Grenadines, is sometimes called the Tahiti of the West Indies. Laze away the day on Chatham Bay, said to be the most beautiful beach in the Grenadines. Find your smile on tiny Happy Island, built from conch shells. Happy Island’s bar is a popular spot for cold ones and “limin’” – island speak for hanging out.

Bequia

Bequia may be known for its boat building and seafaring heritage, but it’s the seafood pizza at Mac’s that shipmates can’t seem to forget. Be sure to visit the Old Hegg Turtle Sanctuary, but save some time for shopping at tiny boutiques filled with local art, scrimshaw and model boats. A sail, kayak or dive excursion from the white beaches of Bequia completes your visit.

Canouan

The locals’ smiles and laughter are what you’ll remember most about Canouan. Who wouldn’t be happy living in paradise? Pristine beaches and secluded hideaways make for a sultry day.

Carriacou

Take a step back in time to the real Caribbean. Known for their boat building and seafaring skills, Carriacou locals can trace their ancestry to Africa and Scotland. Explore the old cemetery, and find centuries-old markers. Feast on fresh-caught lobster in season, or grab a snorkel and take a short swim to the coral reefs, which teem with colorful marine life.

Grenada

Banter and bargain for fresh nutmeg with the friendly spice ladies in the colorful and vibrant spice market in the capital city of St. George’s. Shop for souvenirs and jewelry in the waterfront boutiques, and wet your whistle with a cold rum punch at a local watering hole. Days are filled with picturesque harbors, white sand beaches and lush rainforests. Come see for yourself, and let Grenada add spice to your life.

Mayreau

Take a hike through the village to the other side of Mayreau for a refreshing swim in gleaming Saltwhistle Bay, arguably the most beautiful bay in the Caribbean. Be sure to stop at the crest of the hill by the church for a majestic view of Tobago Cays, Canouan and Union Island. The highlight of any visit to Mayreau is the Cultural Walk, a progressive tour of local watering holes that offers an “intoxicating” taste of the local nightlife.

Mustique

Hang out with royals and rock stars at Basil’s Bar, but take time to discover the wonders of this lovely little hideaway.

Petit St. Vincent

A little slice of heaven on earth for those who love a beach bar, and a beautiful beach.

Sandy Island

All we really need in life are palm trees, a cooler full of ice cold beverages, and the powder white shores of Sandy Island. Care to join us?

St. Lucia

St. Lucia is romantic, a little wild and very seductive. Imagine an afternoon swim in the shadow of the majestic Pitons, or a drive to the top off a volcano, to watch it bubble and steam. Zip-line through the tree tops of the lush rainforest, mountain bike, sail, golf and dive. Eco-adventurers will have a thrill a minute; everyone else will just be thrilled!

St. Vincent

Play in beautiful Wallilabou Bay where Pirates of the Caribbean was filmed. See ancient Amerindian rock carvings at the Layou Petroglyph Park. Stroll the cobblestone streets of Kingstown and get to know the locals in the bustling marketplace. Take in the beauty of the fertile Mesopatamia Valley, where crops, fruit, vegetables and spices are grown.

Tobago Cays

Why settle for one perfect uninhabited islet when you can have many? Tobago Cays are what tropical dreams are made of: stretches of unspoiled beaches, water as clear as glass, and “t-shirt trees” that beg you to bring unique home colorful souvenirs. You'll be counting the days until you can return!

Union Island

Volcanic Union Island, the southernmost island of St Vincent and the Grenadines, is sometimes called the Tahiti of the West Indies. Laze away the day on Chatham Bay, said to be the most beautiful beach in the Grenadines. Find your smile on tiny Happy Island, built from conch shells. Happy Island’s bar is a popular spot for cold ones and “limin’” – island speak for hanging out.

Young Island

Happiness is basking in the sun on pearly white powder beaches, or taking a hike on one of the many trails that criss-cross the island. Slip into brilliant blue water for a swim, and call it a perfect day.

Island Windjammers

ALWAYS ON ISLAND TIME

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