Island Windjammers

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!

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.

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.

Homeport: Frigate Bay, St. Kitts
2023 February | March – VELA
2024 April | May | June – 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.

Homeport: Philipsburg, St. Maarten
2023 January | February – VELA
2024 February | March | April – 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
2023 Year-Round – DIAMANT
2023 October, November – VELA
2024 October – VELA
2024 June | July | August | November | December – DIAMANT

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!

Homeport: Road Town, Tortola
2023 April | May – VELA

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!

Homeport: Providenciales (Provo), Turks and Caicos
2024 February | March | April | May – DIAMANT

Extended sailings are perfect for those who prefer a schedule ruled by the sun, moon and tides. The ports of call are not pre-planned. Each day will bring a new destination – a perfect little island present, wrapped in palm trees, white sands, and turquoise waters.

Save a lot on high season 12-night Explorer cruises, save even more on 12-night Captain’s Specials.