Island Windjammer Cruises

Sail the Leeward Islands with Island Windjammers

“To the Indies!” shouted explorers and pirates from the decks of tall ships. Set a course for the Leeward Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting to be conquered by adventurers like you.

6 Night Leeward Islands Cruises

Home port:
Philipsburg, St. Maarten

Visit a selection of:
Anguilla, Nevis, St. Barths, St.Kitts,
St. Maarten

12 Night Explorer Leeward Islands Cruises

Home port:
Philipsburg, St. Maarten or Marigot Bay

Visit a selection of:
Anguilla, Antigua, Dominica (Portsmouth & Roseau), Guadeloupe, Iles des Saintes, Martinique, Montserrat, Nevis, St. Barths, St. Eustatius, St. Kitts, St. Lucia
Island Windjammers Cruises: Caribbean Sailing Cruise Destinations

Embark: 12:30pm- 2pm / Disembark: No later than 10AM

Anguilla

Take a romantic stroll on your own private slice of brilliant white sand. Hunt for seashells, feel the breeze, and gaze at incredible horizons. Indulge in the delightfully delicious cuisine offered at casually sophisticated island restaurants. Late nights will find you enjoying the local music scene, as the rhythm of reggae and string quartets fill the night air. It’s everything you’ve heard, and more! Anguilla will be your paradise found.

Antigua

Pinkies up! You can trace Antigua’s English roots to Admiral Horatio Nelson and the Royal Navy, who took shelter in the picturesque harbors over 200 years ago. Today, Antigua is more than high tea and crumpets. From helicopter rides to romantic horseback riding, and a different beach for every day of the year, Antigua has it all.

Dominica

You’ll love the nature when you visit Dominica. Take a short hike to majestic Trafalgar Falls, or how about a slow and easy ride down a mangrove-lined, lazy river? Visit the second largest boiling lake in the world, or watch women weave baskets at the Kalinago Culture Village. Top off your day with a romantic swim in Champagne Beach, where tiny bubbles escape from vents in the ocean floor and surround you.

Guadeloupe

Shaped like a butterfly, Guadeloupe’s wings flutter into your adventure loving heart. Beach lovers head east to Grand-Terre for miles of white sand and aqua shores. Hikers, history buffs and those looking to shop may prefer the west wing of Basse-Terre, with its winding trails, lush plant life and tempting boutiques. Snorkelers and Scuba Divers should check out tiny Pigeon Island, home to Jacque Cousteau’s underwater reserve.

Iles des Saintes

Picturesque and serene, Iles des Saintes is an island archipelago of French delights. Cruise around in a glass bottom kayak, grab a baguette and a bottle of wine and head to Pompierre Beach, or take a hike to Fort Napolean.

Martinique

Rhum, ruins and a smoldering volcano are only part of Martinique’s story. She’s as French as a croissant and as elegant as Coco Chanel. Her gorgeous beaches, fashionable shops, fabulous restaurants, and flora filled nature preserve make Martinique a sophisticated island, balanced with tropical chic.

Montserrat

When the volcano erupted in 1997, the locals had already abandoned their homes and businesses in the capital of Plymouth. Nearly two thirds of the island is located in the Exclusion Zone. Tours are offered weather permitting and when the still active volcano is dormant. To the North, Montserrat’s beaches are a lovely shade of pearl grey that shimmers in the sunlight. Sport fishing, kayaking and snorkeling are popular activities.

Nevis

Halos of white puffy clouds floating high atop Nevis Peak remind us that we’re close to heaven on earth. Gingerbread-trimmed cottages and old plantations dot the countryside. Take a hike, play golf, or spend a decadent day doing nothing but sifting sand through your toes on a perfect beach. And don’t miss the Killer Bees at Sunshine’s!

St. Barths

Millionaires, rock stars and sailors like you eat cheeseburgers in paradise at Le Select, the inspiration for Jimmy Buffet’s song. Marvelous beaches, gastronomical delights, and bistros made for people watching and sipping fine French wines…it’s an ooh la-la kind of day, St. Bart’s style!

St. Eustatius

With a few kicks of your fins, you’ll find yourself in a diver’s paradise. The waters surrounding Statia are cluttered with shipwrecks that provide an underwater sanctuary for colorful coral and rare fish. Take a hike to The Quill, an extinct volcano—then cool off with one more dip in the azure Caribbean Sea.

St. Kitts

Take in the view from Brimstone Hill, or wander off and enjoy high tea at a historic plantation. Go bird watching, monkey spotting or snorkeling. Check out Caribelle Batik, located in historic Romney Manor. Take home a beautiful island-inspired wall hanging, or clothing made by a local artisan.

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. Maarten

One island, two countries – one side French, the other Dutch. Does that make it twice as nice? We think so! Put your money on red in a world-class casino, or on black — the little black dress you discovered in a chic boutique. Sail America’s Cup, and celebrate your victory with a bottle of champagne at an au natural beach. Sint Maarten / St. Martin, in any language, is your kind of paradise!

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)
Mar 26, 2017 - Apr 01, 2017 Sagitta RT St Maarten
Rates from $2,025
Apr 02, 2017 - Apr 08, 2017 Sagitta RT St Maarten
Rates from $2,025
Nov 12, 2017 - Nov 18, 2017 Sagitta RT St Maarten
Rates from $1,825
Nov 19, 2017 - Nov 25, 2017 Sagitta RT St Maarten
Rates from $1,825
Nov 26, 2017 - Dec 02, 2017 Sagitta RT St Maarten
Rates from $1,825
Dec 03, 2017 - Dec 09, 2017 Sagitta RT St Maarten
Rates from $1,825
Dec 10, 2017 - Dec 16, 2017 Sagitta RT St Maarten
Rates from $1,825
Dec 17, 2017 - Dec 23, 2017 Sagitta RT St Maarten
Rates from $1,825
Dec 24, 2017 - Dec 30, 2017 Sagitta RT St Maarten
Rates from $2,100
Dec 31, 2017 - Jan 06, 2018 Sagitta RT St Maarten
Rates from $2,100
Feb 04, 2018 - Feb 10, 2018 Sagitta RT St Maarten
Rates from $2,100
Feb 11, 2018 - Feb 17, 2018 Sagitta RT St Maarten
Rates from $2,100
Feb 18, 2018 - Feb 24, 2018 Sagitta RT St Maarten
Rates from $2,100
Feb 25, 2018 - Mar 03, 2018 Sagitta RT St Maarten
Rates from $2,100
Mar 04, 2018 - Mar 10, 2018 Sagitta RT St Maarten
Rates from $2,100
Mar 11, 2018 - Mar 17, 2018 Sagitta RT St Maarten
Rates from $2,100
Mar 18, 2018 - Mar 24, 2018 Sagitta RT St Maarten
Rates from $2,100
Mar 25, 2018 - Mar 31, 2018 Sagitta RT St Maarten
Rates from $2,100
Nov 18, 2018 - Nov 24, 2018 Sagitta RT St Maarten
Rates from $1,900
Nov 25, 2018 - Dec 01, 2018 Sagitta RT St Maarten
Rates from $1,900
Dec 02, 2018 - Dec 08, 2018 Sagitta RT St Maarten
Rates from $1,900
Solo Sojourn - Online booking disabled. Call to reserve.
Dec 09, 2018 - Dec 15, 2018 Sagitta RT St Maarten
Rates from $1,900
Dec 16, 2018 - Dec 22, 2018 Sagitta RT St Maarten
Rates from $1,900
Dec 23, 2018 - Dec 29, 2018 Sagitta RT St Maarten
Rates from $2,150
Island Windjammers

ALWAYS ON ISLAND TIME

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