Island Windjammer Cruises

Leeward Islands

“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.

Choose the Leewards if you’re looking for cultural diversity along with a nice balance of small islands and larger ports with just the right amount of hustle and bustle.

This is a great itinerary for first timers to the Caribbean.

6 NIGHT SOUTHERN LEEWARD CRUISE
Home port: Frigate Bay, St. Kitts
Visit a selection of:
Antigua | Guadeloupe | Montserrat | Nevis | St. Kitts
6 NIGHT NORTHERN LEEWARD CRUISE
Home port: Philipsburg, St. Maarten
Visit a selection of:
Anguilla | Nevis | St. Barths | St. Kitts
St. Maarten

12 NIGHT LEEWARD + FRENCH WEST INDIES CRUISE
Home port: Philipsburg, St. Maarten and Marigot Bay,
St. Lucia
Visit a selection of:
Anguilla | Antigua | Dominica | Guadeloupe
Iles des Saintes | Martinique | Montserrat | Nevis
St. Barths | St. Kitts | St. Lucia
12 NIGHT LEEWARD ISLAND CRUISE
Home port: Frigate Bay, St. Kitts
Visit a selection of:
Anguilla | Antigua | Guadeloupe
Iles des Saintes | Martinique | Montserrat
Nevis | St. Barths | St. Kitts
 
12 NIGHT BRITISH VIRGIN + LEEWARD ISLAND CRUISE
Home port: Road Town, Tortola + Philipsburg,
St. Maarten
Visit a selection of:
Anguilla | Cooper Island | Jost Van Dyke | Nevis | Norman Island | Salt Island | St. Barths | St. Kitts | St. Maarten
Tortola | Virgin Gorda
 
Island Windjammers Cruises: Caribbean Sailing Cruise Destinations

Embark 2 PM | Disembark 10 AM

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.

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.

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. 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 side 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 that you discovered in a chic boutique. Sail the America’s Cup, and celebrate your victory with a bottle of champagne at an "au naturel" 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.

Cooper Island

The Cooper Island Beach Club is the focal point of this charming little island. Take a dip from the white sand beach, and be wowed by the fantastic snorkeling at Little Carvel Rock.  Later, have a bite at the open-air restaurant, and pick up something pretty at the boutique. A sunset nip or two of rum from the well-stocked shop is the perfect end to a memorable day.

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.

Jost Van Dyke

Named for a Dutch pirate, Jost Van Dyke has likely inspired a number of your favorite trop rock songs. Think beach bars, bikinis and hammocks. Sip a Painkiller at the Soggy Dollar Bar and celebrate life at world famous Foxy’s.

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!

Norman Island

Let loose your inner pirate, and dive for treasure in The Caves of Norman Island. Surrounded by lovely bays and offshore reefs, divers get their fill of superb snorkeling.

Salt Island

Named for the salt ponds that were once an important resource, Salt Island is best known for the wreck of the Rhone. Scenes from the movie “The Deep” were filmed here. Whether you scuba or snorkel, you’ll be amazed at how perfectly-preserved this shipwreck is, and will marvel at the aquatic life it attracts.

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. 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 side 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 that you discovered in a chic boutique. Sail the America’s Cup, and celebrate your victory with a bottle of champagne at an "au naturel" beach. Sint Maarten / St. Martin, in any language, is your kind of paradise!

Tortola

Sink your toes into the golden beaches of the island Columbus named “land of the turtle dove.” There are beaches for snorkeling, surfing, kayaking and paddle boarding. Once you’ve had your fill of life aquatic, take time to explore Road Town’s art galleries and museums. Be sure to stop in at Pussers for your daily ration of grog! Nature lovers may prefer the wilder side of Tortola; rugged mountain trails, bat caves and sloping green hills are waiting to be discovered.

Virgin Gorda

Swim, snorkel, and play hide and seek among the giant granite boulders of The Baths. Take a walk around Spanish Town, explore The Copper Mine on the southeastern tip of the island, and take in the vistas.

Island Windjammers

ALWAYS ON ISLAND TIME