Island Windjammer Cruises

Summer | Fall

Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
Island Windjammers Cruises - Caribbean Tall Ship Sailing Cruises
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2020   Summer | Fall

Wrap yourself in a lush blanket of green as you trek through the rainforest to the sound of wild macaws and cascading waterfalls.

Take an afternoon swim in the shadow of the majestic Pitons; try horseback riding or ziplining. You might happen upon an abandoned plantation, or a smoldering volcano that serves to remind you that the hearts of these islands beat to the rhythm of nature.

Savor Creole cuisine with the locals in a picturesque fishing village where colorful gingerbread houses dot the seashore. Eclectic island boutiques and open-air markets feature Caribbean madras, one-of-a-kind jewelry, French perfumes and locally distilled rhum.

Sail around the bend to a secret oasis and sip a “sundowner” as the day comes to an end, and the stars light up the sky to guide the way home. If you love nature, boutiques, and a touch of French culture, this is the adventure for you!

Home port: Rodney Bay, St. Lucia
Offered: November – VELA

If your perfect escape includes secluded isles ringed with white sand beaches and swaying palms, allow us to tempt you with a sail through the Windward Islands!

You’ll swim with sea turtles in the protected waters of marine preserves, and snorkel above colorful reefs that come alive with waving sea fans and electric blue damselfish.

Hike to spectacular vistas, and snap yourself next to cannons protecting the ruins of old forts. Purchase a unique piece of scrimshaw or a handcrafted model boat from a local artisan.

Experience the local nightlife with an intoxicating “cultural walk”. Lime with the locals and dance the night away on this progressive tour of island-style watering holes!

Home port: St. George’s Grenada
Offered: November – DIAMANT

2021   Summer | Fall

The British loved their sea battles, and left plenty of evidence of that behind in this corner of the Caribbean. Explore sprawling hillside fortresses for magnificent views and plentiful photo-ops.

Enjoy high tea at a historic plantation, stroll the gardens, and delight in the beautiful foliage. Choose a handmade, island-inspired batik sarong to wear to the beach bonfire. Go bird-watching and monkey spotting.

Pearl-gray beaches shimmer in the sunlight like diamonds, a reminder of the dormant but still active volcano that erupted in 1997. Don’t worry--we know where to go when and if it decides to blow!

Puffy clouds float like halos around mountain peaks, and remind us how close we are to heaven on earth. Have a decadent day sipping Killer Bees and sifting sand through your toes.

Home port: Frigate Bay, St. Kitts
Offered: End of May – VELA

Wrap yourself in a lush blanket of green as you trek through the rainforest to the sound of wild macaws and cascading waterfalls.

Take an afternoon swim in the shadow of the majestic Pitons; try horseback riding or ziplining. You might happen upon an abandoned plantation, or a smoldering volcano that serves to remind you that the hearts of these islands beat to the rhythm of nature.

Savor Creole cuisine with the locals in a picturesque fishing village where colorful gingerbread houses dot the seashore. Eclectic island boutiques and open-air markets feature Caribbean madras, one-of-a-kind jewelry, French perfumes and locally distilled rhum.

Sail around the bend to a secret oasis and sip a “sundowner” as the day comes to an end, and the stars light up the sky to guide the way home. If you love nature, boutiques, and a touch of French culture, this is the adventure for you!

Homeport: Rodney Bay, St. Lucia
Offered: June | July | October – VELA

Your adventure begins in Sint Maarten / St. Maarten: one island, two countries. The Dutch side offers a bustling downtown with casinos, chic boutiques, and the chance to sail America’s Cup! The French prefer their beaches “au naturel”, so leave your inhibitions at the invisible border.

Devour a juicy cheeseburger in paradise at Le Select, the inspiration for Jimmy Buffett’s song. Shopping is fabby at high-end boutiques (and semi-reasonable ones, too)! Get a swim in and sip a grapefruit margarita at a chichi beach club.

Today is another day in paradise! You get to paddleboard, snorkel, and hike trails that lead to majestic views. No shopping, no WIFI; just you getting to know the pristine nature preserve.

Tasty Guavaberry Coladas and other passion-inspiring frosty concoctions tempt your tastebuds. Beach bars are plentiful but don’t miss a day of basking in the sun on a postcard-perfect blinding white crescent beach.

Home port: Philipsburg, St. Maarten
Offered: November – VELA

If your perfect escape includes secluded isles ringed with white sand beaches and swaying palms, allow us to tempt you with a sail through the Windward Islands!

You’ll swim with sea turtles in the protected waters of marine preserves, and snorkel above colorful reefs that come alive with waving sea fans and electric blue damselfish.

Hike to spectacular vistas, and snap yourself next to cannons protecting the ruins of old forts. Purchase a unique piece of scrimshaw or a handcrafted model boat from a local artisan.

Experience the local nightlife with an intoxicating “cultural walk”. Lime with the locals and dance the night away on this progressive tour of island-style watering holes!

Homeport: St. George’s Grenada or Rodney Bay, St. Lucia

Offered: Year Round from Grenada – DIAMANT
Limited Summer options – VELA

2022   Summer | Fall

Wrap yourself in a lush blanket of green as you trek through the rainforest to the sound of wild macaws and cascading waterfalls.

Take an afternoon swim in the shadow of the majestic Pitons; try horseback riding or ziplining. You might happen upon an abandoned plantation, or a smoldering volcano that serves to remind you that the hearts of these islands beat to the rhythm of nature.

Savor Creole cuisine with the locals in a picturesque fishing village where colorful gingerbread houses dot the seashore. Eclectic island boutiques and open-air markets feature Caribbean madras, one-of-a-kind jewelry, French perfumes and locally distilled rhum.

Sail around the bend to a secret oasis and sip a “sundowner” as the day comes to an end, and the stars light up the sky to guide the way home. If you love nature, boutiques, and a touch of French culture, this is the adventure for you!

Homeport: Rodney Bay, St. Lucia
Offered: June | July | November – VELA

If your perfect escape includes secluded isles ringed with white sand beaches and swaying palms, allow us to tempt you with a sail through the Windward Islands!

You’ll swim with sea turtles in the protected waters of marine preserves, and snorkel above colorful reefs that come alive with waving sea fans and electric blue damselfish.

Hike to spectacular vistas, and snap yourself next to cannons protecting the ruins of old forts. Purchase a unique piece of scrimshaw or a handcrafted model boat from a local artisan.

Experience the local nightlife with an intoxicating “cultural walk”. Lime with the locals and dance the night away on this progressive tour of island-style watering holes!

Homeport: St. George’s Grenada or Rodney Bay, St. Lucia

Offered: Year Round from Grenada – DIAMANT
Limited Summer options – VELA
Island Windjammers

ALWAYS ON ISLAND TIME