Island Windjammer Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises
Island Windjammers Cruises - Caribbean and Mediterranean Sailing Cruises

 

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!

2024  June | July | August | November | December – VELA
2025  December – VELA

Homeport:  Frigate Bay, St. Kitts
St Kitts  |  Nevis  |  Antigua

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.

2024  April | May | June – 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.

2024  February | March | April – VELA
2025  January | February | March – 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!

2024  October – VELA
2024  June | July | October | November | December – DIAMANT
2025  November | December – DIAMANT
2025  November – VELA

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!

2024  February | March | April | May – DIAMANT
2025  February | March | April | May – 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

Greek Isles 10 Night Sailings

Homeport:  Kos Town, Kos Island
Kos  |  Panteli  |  Arki  |  Patmos  |  Loipsi  |  Kalymnos  |  Levitha  |  Kefalos  |  Tilos  |  Nisyros

Your adventure begins in Kos, an island paradise located in the southeastern Aegean Sea. From here, you will island-hop to ports of call rich in history and culture.

Hike to an abandoned church. Watch tiny model boats, built by a loving grandfather for his adoring grandchildren, bob in a cove. Wild goats tempt gravity on the rocky hillsides. Swim in the clear, indigo blue sea, and dry yourself under the warm rays of the Mediterranean sun.

Explore towns and villages. Shop at the local markets, and admire the strikingly white buildings, framed by incredibly blue, cloudless skies.

Slip away to a vine-covered taverna and partake in the endless pitchers of local wine sipped by visitors and festive locals. Dine on delicious octopus, and savor the ripe tomatoes in a chunky Greek salad. Indulge in a bowl of creamy homemade yogurt, drizzled in golden honey.

Overnight in a sheltered bay next to an ancient monastery. Breathe in the salt air and calmness of the night, as you gaze at the twinkling stars above. If you listen closely, you might hear soft music wafting through the galaxies from Lyra, the harp constellation.

2024 + 2025  April| May| June| July| August| September| October – LYRA

Caribbean 12 Night Sailings

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.

DIAMANT
January 7 - 19, 2024
Windward Islands + French West Indies
Home port: St. George’s, Grenada + Rodney Bay, St. Lucia
Visit a selection of:
Bequia  |  Canouan  |  Carriacou  |  Grenada  |  Mayreau  |  Petit St. Vincent  |  Sandy Island  |  St. Lucia  |  St. Vincent  |  Tobago Cays
Union Island  |  Young Island

January 21 - February 2, 2024
Leeward + French West Indies
Home port: Rodney Bay, St. Lucia + Philipsburg, St. Maarten
Visit a selection of:
Anguilla  |  Antigua  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts
St. Lucia  |  St. Maarten

VELA
January 7 - 9, 2024
January 21 - February 2, 2024
British Virgin Islands + Leeward
Home port: Road Town, Tortola + Philipsburg, St.Maarten
Visit a selection of:
Anguilla  |  Cooper Island  |  Jost Van Dyke  |  Norman Island  |  St. Barths  |  Salt Island  |  Tortola  |  Virgin Gorda

DIAMANT
May 26 - June 7, 2024
Leeward + French West Indies
Home port: Rodney Bay, St. Lucia + Philipsburg, St. Maarten
Visit a selection of:
Anguilla  |  Antigua  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts
St. Lucia  |  St. Maarten

June 9 - 21, 2024
Windwards + French West Indies
Home port: St. George’s, Grenada + Rodney Bay, St. Lucia
Visit a selection of:
Bequia  |  Canouan  |  Carriacou  |  Grenada  |  Mayreau  |  Petit St. Vincent  |  Sandy Island  |  St. Lucia  |  St. Vincent  |  Tobago Cays
Union Island  |  Young Island

VELA
April 14 - 26, 2024
French West Indies
Home port: Philipsburg, St. Maarten + Frigate Bay, St. Kitts
Visit a selection of:
Anguilla  |  Antigua  |  Dominica  |  Montserrat  |  Nevis  |  Saba  |  St. Barths  |  St. Kitts  |  St. Maarten

June 9 – 21, 2024
French West Indies
Home port: Frigate Bay, St. Kitts + Rodney Bay, St. Lucia
Visit a selection of:
Anguilla  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts  |  St. Lucia

December 8 – 20, 2024
French West Indies
Home port: Rodney Bay, St. Lucia
Visit a selection of:
Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Kitts  |  St. Lucia

DIAMANT
December 22, 2024 to January 3, 2025
Windward Islands + French West Indies
Home port: St. George’s, Grenada + Rodney Bay, St. Lucia
Visit a selection of:
Bequia  |  Canouan  |  Carriacou  |  Grenada  |  Mayreau  |  Petit St. Vincent  |  Sandy Island  |  St. Lucia  |  St. Vincent  |  Tobago Cays
Union Island  |  Young Island

January 5 - 17, 2025
French West Indies + Leeward
Home port: Rodney Bay, St. Lucia + Philipsburg, St. Maarten
Visit a selection of:
Anguilla  |  Antigua  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts
St. Lucia  |  St. Maarten

VELA
Jan 5 - 17, 2025
French West Indies
Home port: Rodney Bay, St. Lucia + Frigate Bay, St. Kitts
Visit a selection of:
Anguilla  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts  |  St. Lucia

March 16 - 28, 2025
Leeward + British Virgin Islands
Home port: Philipsburg, St. Maarten + Road Town, Tortola
Visit a selection of:
Anguilla  |  Cooper Island  |  Jost Van Dyke  |  Norman Island  |  St. Barths  |  Salt Island  |  Tortola  |  Tortola  |  Virgin Gorda

DIAMANT
May 25 - June 6, 2025
French West Indies + Leeward
Home port: Philipsburg, St. Maarten + Rodney Bay, St. Lucia
Visit a selection of:
Anguilla  |  Antigua  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts
St. Lucia  |  St. Maarten

June 8 - June 20, 2025
French West Indies + Windward Islands
Home port: Rodney Bay, St. Lucia + St. George’s, Grenada
Visit a selection of:
Bequia  |  Canouan  |  Carriacou  |  Grenada  |  Mayreau  |  Petit St. Vincent  |  Sandy Island  |  St. Lucia  |  St. Vincent  |  Tobago Cays
Union Island  |  Young Island

December 7 - 19, 2025
Windward Islands
Home port: St. George’s, Grenada
Visit a selection of:
Bequia  |  Canouan  |  Carriacou  |  Grenada  |  Mayreau  |  Petit St. Vincent  |  Sandy Island  |  St. Vincent  |  Tobago Cays  |  Union Island  |  Young Island

VELA
May 11 - 23, 2025
British Virgin Islands + Leeward
Home port: Road Town, Tortola + Philipsburg, St.Maarten
Visit a selection of:
Anguilla  |  Cooper Island  |  Jost Van Dyke  |  Norman Island  |  St. Barths  |  Salt Island  |  Tortola  |  Virgin Gorda

May 25 - June 6, 2025
French West Indies
Home port: Frigate Bay, St. Kitts + Rodney Bay, St. Lucia
Visit a selection of:
Anguilla  |  Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Barths  |  St. Kitts  |  St. Lucia

November 16 - 28, 2025
Windwards + French West Indies
Home port: St. George’s, Grenada + Rodney Bay, St. Lucia
Visit a selection of:
Bequia  |  Canouan  |  Carriacou  |  Grenada  |  Mayreau  |  Petit St. Vincent  |  Sandy Island  |  St. Lucia  |  St. Vincent  |  Tobago Cays
Union Island  |  Young Island

November 30 - December 12, 2025
French West Indies
Home port: Rodney Bay, St. Lucia
Visit a selection of:
Dominica  |  Guadeloupe  |  Iles des Saintes  |  Martinique  |  Montserrat  |  Nevis  |  St. Kitts  |  St. Lucia

Island Windjammers

ALWAYS ON ISLAND TIME