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.

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. 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. 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!

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!

Island Windjammers

ALWAYS ON ISLAND TIME

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