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.

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.

Cruise rates are inclusive of all onboard meals and snacks, beverages (water, juice, soda, beer, wine, and rum punch), port charges and taxes, and complimentary use of snorkel gear for the week.

Rates are in US funds, per person based upon double occupancy, unless noted otherwise. Please see our Cruise Terms & Conditions for more information.

Sailing Dates Ship Embark/
Disembark
Cabin Pricing (Per Person)
Feb 26, 2017 - Mar 04, 2017 Diamant RT Grenada
Rates from $2,725
Mar 05, 2017 - Mar 11, 2017 Diamant RT Grenada
Rates from $2,725
Mar 05, 2017 - Mar 11, 2017 Vela RT St Lucia
Rates from $2,325
Mar 12, 2017 - Mar 18, 2017 Diamant RT Grenada
Rates from $2,725
Mar 19, 2017 - Mar 25, 2017 Diamant RT Grenada
Rates from $2,725
Mar 19, 2017 - Mar 25, 2017 Vela RT St Lucia
Rates from $2,325
Mar 26, 2017 - Apr 01, 2017 Diamant RT Grenada
Rates from $2,725
Apr 02, 2017 - Apr 08, 2017 Diamant RT Grenada
Rates from $2,725
Apr 09, 2017 - Apr 15, 2017 Diamant RT Grenada
Rates from $2,725
Apr 16, 2017 - Apr 22, 2017 Diamant RT Grenada
Rates from $2,725
Apr 23, 2017 - Apr 29, 2017 Diamant RT Grenada
Rates from $2,725
Apr 30, 2017 - May 06, 2017 Diamant RT Grenada
Rates from $2,725
Apr 30, 2017 - May 06, 2017 Vela RT St Lucia
Rates from $2,325
May 07, 2017 - May 13, 2017 Diamant RT Grenada
Rates from $2,725
May 14, 2017 - May 26, 2017 Diamant RT Grenada
Rates from $3,825
12 Night Explorer - Captain's Special
May 28, 2017 - Jun 03, 2017 Diamant RT Grenada
Rates from $2,525
May 28, 2017 - Jun 03, 2017 Vela RT St Lucia
Rates from $2,125
Jun 04, 2017 - Jun 10, 2017 Diamant RT Grenada
Rates from $2,525
Jun 11, 2017 - Jun 17, 2017 Diamant RT Grenada
Rates from $2,525
Jun 11, 2017 - Jun 17, 2017 Vela RT St Lucia
Rates from $2,125
Jun 18, 2017 - Jun 24, 2017 Diamant RT Grenada
Rates from $2,525
Jun 25, 2017 - Jul 01, 2017 Diamant RT Grenada
Rates from $2,525
Jun 25, 2017 - Jul 01, 2017 Vela RT St Lucia
Rates from $2,125
Jul 02, 2017 - Jul 08, 2017 Diamant RT Grenada
Rates from $2,525
Jul 02, 2017 - Jul 08, 2017 Sagitta RT Grenada
Rates from $1,825
Jul 09, 2017 - Jul 15, 2017 Sagitta RT Grenada
Rates from $1,825
Jul 09, 2017 - Jul 15, 2017 Diamant RT Grenada
Rates from $2,525
Jul 16, 2017 - Jul 22, 2017 Diamant RT Grenada
Rates from $2,525
Jul 16, 2017 - Jul 22, 2017 Sagitta RT Grenada
Rates from $1,825
Jul 23, 2017 - Jul 29, 2017 Sagitta RT Grenada
Rates from $1,825
Jul 23, 2017 - Jul 29, 2017 Diamant RT Grenada
Rates from $2,525
Jul 30, 2017 - Aug 05, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Jul 30, 2017 - Aug 05, 2017 Sagitta RT Grenada
Rates from $1,325
August & September Savings
Aug 06, 2017 - Aug 12, 2017 Sagitta Grenada/
St Lucia
Rates from $1,325
August & September Savings
Aug 06, 2017 - Aug 12, 2017 Diamant Grenada/
St Lucia
Rates from $2,025
August & September Savings
Aug 13, 2017 - Aug 19, 2017 Diamant St Lucia/
Grenada
Rates from $2,025
August & September Savings
Aug 20, 2017 - Aug 26, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Aug 27, 2017 - Sep 02, 2017 Vela RT Grenada
Rates from $1,625
August & September Savings
Aug 27, 2017 - Sep 02, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Sep 03, 2017 - Sep 09, 2017 Vela RT Grenada
Rates from $1,625
Pirate Week - August & September Savings
Sep 03, 2017 - Sep 09, 2017 Diamant RT Grenada
Rates from $2,025
Pirate Week - August & September Savings
Sep 10, 2017 - Sep 16, 2017 Vela RT Grenada
Rates from $1,625
August & September Savings
Sep 10, 2017 - Sep 16, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Sep 17, 2017 - Sep 23, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Sep 17, 2017 - Sep 23, 2017 Vela RT Grenada
Rates from $1,625
Taste of the Islands - August & September Savings
Sep 24, 2017 - Sep 30, 2017 Vela RT Grenada
Rates from $1,625
August & September Savings
Sep 24, 2017 - Sep 30, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Oct 01, 2017 - Oct 07, 2017 Diamant RT Grenada
Rates from $2,025
August & September Savings
Oct 01, 2017 - Oct 07, 2017 Vela RT Grenada
Rates from $1,625
August & September Savings
Oct 08, 2017 - Oct 14, 2017 Vela Grenada/
St Lucia
Rates from $2,125
Nov 05, 2017 - Nov 11, 2017 Vela RT St Lucia
Rates from $2,125
Nov 05, 2017 - Nov 11, 2017 Diamant RT Grenada
Rates from $2,525
Nov 12, 2017 - Nov 18, 2017 Diamant RT Grenada
Rates from $2,525
Nov 19, 2017 - Nov 25, 2017 Diamant RT Grenada
Rates from $2,525
Nov 19, 2017 - Nov 25, 2017 Vela RT St Lucia
Rates from $2,125
Nov 26, 2017 - Dec 02, 2017 Diamant RT Grenada
Rates from $2,525
Dec 03, 2017 - Dec 15, 2017 Diamant RT Grenada
Rates from $4,325
12 Night Explorer Cruise
Dec 03, 2017 - Dec 09, 2017 Vela RT St Lucia
Rates from $2,125
Dec 17, 2017 - Dec 23, 2017 Diamant RT Grenada
Rates from $2,525
Dec 24, 2017 - Dec 30, 2017 Diamant RT Grenada
Rates from $2,800
Dec 31, 2017 - Jan 06, 2018 Diamant RT Grenada
Rates from $2,800
Jan 07, 2018 - Jan 19, 2018 Diamant Grenada/
St Lucia
Rates from $4,475
12 Night Explorer Cruise
Jan 21, 2018 - Feb 02, 2018 Diamant St Lucia/
Grenada
Rates from $4,475
12 Night Explorer Cruise
Feb 04, 2018 - Feb 10, 2018 Diamant RT Grenada
Rates from $2,800
Feb 11, 2018 - Feb 17, 2018 Diamant RT Grenada
Rates from $2,800
Feb 18, 2018 - Feb 24, 2018 Diamant RT Grenada
Rates from $2,800
Feb 25, 2018 - Mar 03, 2018 Diamant RT Grenada
Rates from $2,800
Mar 04, 2018 - Mar 10, 2018 Diamant RT Grenada
Rates from $2,800
Mar 11, 2018 - Mar 17, 2018 Diamant RT Grenada
Rates from $2,800
Mar 18, 2018 - Mar 24, 2018 Diamant RT Grenada
Rates from $2,800
Mar 25, 2018 - Mar 31, 2018 Diamant RT Grenada
Rates from $2,800
Apr 01, 2018 - Apr 07, 2018 Diamant RT Grenada
Rates from $2,800
Apr 08, 2018 - Apr 14, 2018 Diamant RT Grenada
Rates from $2,800
Apr 15, 2018 - Apr 21, 2018 Diamant RT Grenada
Rates from $2,800
Apr 22, 2018 - Apr 28, 2018 Diamant RT Grenada
Rates from $2,800
Apr 29, 2018 - May 05, 2018 Diamant RT Grenada
Rates from $2,800
May 06, 2018 - May 12, 2018 Diamant RT Grenada
Rates from $2,800
May 13, 2018 - May 25, 2018 Diamant RT Grenada
Rates from $3,975
12 Night Explorer - Captain's Special
May 27, 2018 - Jun 02, 2018 Diamant RT Grenada
Rates from $2,600
Jun 03, 2018 - Jun 09, 2018 Diamant RT Grenada
Rates from $2,600
Jun 10, 2018 - Jun 16, 2018 Diamant RT Grenada
Rates from $2,600
Jun 17, 2018 - Jun 23, 2018 Diamant RT Grenada
Rates from $2,600
Jun 24, 2018 - Jun 30, 2018 Diamant RT Grenada
Rates from $2,600
Jul 01, 2018 - Jul 07, 2018 Diamant RT Grenada
Rates from $2,600
Jul 08, 2018 - Jul 14, 2018 Diamant RT Grenada
Rates from $2,600
Jul 15, 2018 - Jul 21, 2018 Diamant RT Grenada
Rates from $2,600
Jul 22, 2018 - Jul 28, 2018 Sagitta St Lucia/
Grenada
Rates from $1,900
Jul 29, 2018 - Aug 04, 2018 Sagitta RT Grenada
Rates from $1,400
August & September Savings
Aug 05, 2018 - Aug 11, 2018 Sagitta Grenada/
St Lucia
Rates from $1,400
August & September Savings
Aug 12, 2018 - Aug 18, 2018 Sagitta St Lucia/
Grenada
Rates from $1,400
August & September Savings
Aug 19, 2018 - Aug 25, 2018 Sagitta RT Grenada
Rates from $1,400
August & September Savings
Aug 19, 2018 - Aug 25, 2018 Vela St Lucia/
Grenada
Rates from $1,700
August & September Savings
Aug 26, 2018 - Sep 01, 2018 Vela RT Grenada
Rates from $1,700
August & September Savings
Aug 26, 2018 - Sep 01, 2018 Sagitta RT Grenada
Rates from $1,400
August & September Savings
Sep 02, 2018 - Sep 08, 2018 Sagitta RT Grenada
Rates from $1,400
August & September Savings
Sep 02, 2018 - Sep 08, 2018 Vela RT Grenada
Rates from $1,700
August & September Savings
Sep 09, 2018 - Sep 15, 2018 Vela RT Grenada
Rates from $1,700
August & September Savings
Sep 09, 2018 - Sep 15, 2018 Diamant RT Grenada
Rates from $2,100
August & September Savings
Sep 16, 2018 - Sep 22, 2018 Diamant RT Grenada
Rates from $2,100
August & September Savings
Sep 16, 2018 - Sep 22, 2018 Vela RT Grenada
Rates from $1,700
August & September Savings
Sep 23, 2018 - Sep 29, 2018 Vela RT Grenada
Rates from $1,700
Pirate Week - August & September Savings
Sep 23, 2018 - Sep 29, 2018 Diamant RT Grenada
Rates from $2,100
Pirate Week - August & September Savings
Sep 30, 2018 - Oct 06, 2018 Diamant RT Grenada
Rates from $2,600
Sep 30, 2018 - Oct 06, 2018 Vela RT Grenada
Rates from $2,200
Oct 07, 2018 - Oct 13, 2018 Vela RT Grenada
Rates from $2,200
Oct 07, 2018 - Oct 13, 2018 Diamant RT Grenada
Rates from $2,600
Oct 14, 2018 - Oct 20, 2018 Diamant RT Grenada
Rates from $2,600
Oct 14, 2018 - Oct 20, 2018 Vela RT Grenada
Rates from $2,200
Oct 21, 2018 - Oct 27, 2018 Vela RT Grenada
Rates from $2,200
Fleet Week
Oct 21, 2018 - Oct 27, 2018 Sagitta RT Grenada
Rates from $1,900
Fleet Week
Oct 21, 2018 - Oct 27, 2018 Diamant RT Grenada
Rates from $2,600
Fleet Week
Oct 28, 2018 - Nov 03, 2018 Diamant RT Grenada
Rates from $2,600
Oct 28, 2018 - Nov 03, 2018 Sagitta Grenada/
St Lucia
Rates from $1,900
Oct 28, 2018 - Nov 03, 2018 Vela Grenada/
St Lucia
Rates from $2,200
Nov 04, 2018 - Nov 10, 2018 Diamant RT Grenada
Rates from $2,600
Nov 11, 2018 - Nov 17, 2018 Diamant RT Grenada
Rates from $2,600
Nov 18, 2018 - Nov 24, 2018 Diamant RT Grenada
Rates from $2,600
Nov 25, 2018 - Dec 01, 2018 Diamant RT Grenada
Rates from $2,600
Dec 02, 2018 - Dec 14, 2018 Diamant RT Grenada
Rates from $4,475
12 Night Explorer Cruise
Dec 16, 2018 - Dec 22, 2018 Diamant RT Grenada
Rates from $2,600
Dec 23, 2018 - Dec 29, 2018 Diamant RT Grenada
Rates from $2,850
Island Windjammers

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