Island Windjammer Cruises

 

Greek Isles 6 Night Sailings

Homeport:  Athens, Greece
Kea  |  Aegina  |  Kythnos  |  Ydra  |  Spetses  |  Poros

Hike in the footsteps of the gods, encountering ruins of ancient temples. Classical statues and watchtowers built from salmon-pink stone await your wonderment. Inhale the heady scent of citrus and pine, clearing your mind.

Discover a rare pistachio field on the island of Kea. In Aegina, visit a church built on the ruins of the temple of Zeus. Slip into a church in Kythnos and marvel at the hand-carved altars and ornate bishops' thrones. Stroll along the seafront promenade in Poros, sipping a freshly squeezed lemonade.

Unwind on a sun lounger on a beach lapped by the dazzlingly clear Mediterranean. Ouzo and olive oil will be flowing in the nearby tavernas, and smiles will greet you everywhere you go.

2025  June | July | August – LYRA

Caribbean 6 Night Sailings

Homeport:  Rodney Bay, St. Lucia
ST. LUCIA  -  Anse Chastanet  |  Pigeon Island
MARTINIQUE  -  Grande Anse D’Arlets  |  Pt Anse D’Arlets  |  St Pierre

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!

2025  December – VELA

Homeport:  Philipsburg, St. Maarten
St Maarten  |  St Barth's  |  Anguilla

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.

2025  January | February | March – VELA
2026  January | February | March – VELA

Homeport:  Portsmouth, Dominica
Îles de Saintes  |  Guadeloupe  |  Marie Galante

Beauty comes naturally to lush Dominica. Visit the Kalinago territory, go for a rugged hike, and refresh yourself under a cascading waterfall. We'll sail to Guadeloupe and the tiny islets of Iles des Saintes where you can choose your beach by the color of the sand... from brilliant white, to pink, gold, and volcanic black. Savor the delicious coconut sorbet, paddle through mangroves, snorkel magnificent reefs, and swim in protected lagoons.

2026  March | April – VELA

Homeport:  St. George’s Grenada
Carriacou  |  Mayreau  |  Tobago Cays

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!

2025  June | July | November | December – DIAMANT
2025  November – VELA
2026  May | June | November – VELA
2026  November – DIAMANT

Homeport:  Road Town, Tortola
British Virgin Islands

Live the lyrics of your favorite trop rock song, while sipping high-octane rum at legendary beach bars.

Be the first to leave your footprints in a heavenly palm-fringed hideaway. Snorkel the kaleidoscopic offshore reefs. Let loose your inner pirate! Search for buried treasure in a swim-up cave, or in the crevice of a giant boulder.

Kayak under the stars, surf the north coast, and paddleboard in the calm waters of Sir Francis Drake’s Passage.

Once you’ve had your fill of life aquatic, explore the wilder. more rugged side of the British Virgins with a hike on a mountain trail and a peek into a bat cave. Yikes!

There’s no denying the British influence as you stroll the cobblestone streets and pop into art galleries, shops, and museums. Share a pint of grog with your shipmates at a raucous pub. Offer up a toast to sublime sailing, full moon parties, and living a pirate’s life!

2025  March | April | May – VELA

Homeport:  Providenciales (Provo), Turks and Caicos
Turks and Caicos

Take a few swift fin kicks from the brilliantly white sand beach, and you'll be waving hello to friendly moray eels, graceful manta rays, and energetic schools of tropical fish. The Turks and Caicos islands are home to one of the largest barrier reefs in the world! Flocks of pink flamingos stand watch from the shore, awaiting the annual winter migration of humpback whales. Savor a rummy-delicious Caribbean cake, and "wine" in time to the beat of Ripsaw music. Come for the charm, the luxe, and the sailing divine!

2025  February | March | April | May – DIAMANT
2026  February | March – DIAMANT

Homeport:  Young Island, St. Vincent
Bequia  |  Canouan  |  Mustique  |  Tobago Cays

If you listen closely, you'll hear a mermaid's laughter rising from the turquoise deep, while pods of migrating whales murmur and sing their approval. Monkeys chatter. Sparks light up the sky from volcanoes which color the beaches a dark charcoal, speckled with diamond dust.

The West Indies are wild, wonderful, and undiscovered. Immerse yourself in their beauty and hide in plain sight....Sail Vela to sun-dappled islands and find yourself!

2025  June – VELA
2026  Aprl | May – VELA

Itineraries are not guaranteed and are subject to change.

Island Windjammers

ALWAYS ON ISLAND TIME