Windstar Cruise

10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]

10 Days - Blue Waters of the Leeward Islands [Philipsburg, St. Maarten to Philipsburg, St]
Starting from $3,599*

Philipsburg, St. Maarten to Philipsburg, St. Maarten

Ship: Wind Spirit

Departure Date : Jan 14 2026

Itinerary

Day Philipsburg, Sint Maarten
Depart 7:00 PM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
Day Little Bay, Montserrat, BWI
Arrive 8:00 AM, Depart 5:00 PM
Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
Little Bay, Montserrat, BWI
Day Roseau, Dominica
Arrive 8:00 AM, Depart 6:00 PM
"Dominica, an Anglophone island between the French islands of Guadeloupe and Martinique, may well be the most unspoiled of the larger Caribbean islands. With few hotels and no mass tourism to speak of, Dominica is called ""the nature island” for good reason. One of the most dramatic natural wonders in the West Indies sits at the bottom third of the isle. The Boiling Lake is a flooded fumarole (volcanic fissure) whose water emits sulfurous vapors as it bubbles and boils at around 92 degrees Celsius (nearly 200 degrees Fahrenheit). Surrounding the lake is the lush rain forest of Morne Trois Pitons National Park, a UNESCO World Heritage Site. This vital habitat is teeming with birds, tiny tree frogs and vibrant bromeliads. Getting around mountainous Dominica means negotiating winding, twisty roads. The offshore waters are known for some fine diving and whale-watching. With little room to grow, the small capital of Roseau never exploded in size; it still retains many of its colorful colonial-era wooden houses. Street vendors sell everything from fresh fruits and barbecued meats to medicinal herbs and elixirs. "
Roseau, Dominica
Day Castries, Saint Lucia
Arrive 8:00 AM, Depart 8:00 PM
So you think you've "done" the Caribbean? St. Lucia kindly asks you to think again. With mountain peaks, plunging valleys, lush rain forests, historic sites, tropical flora and fauna and the world's only drive-in volcano, this island of 165,000 residents is more than just pretty palm-fringed beaches along a turquoise sea—though there happen to be plenty of those, too. No wonder France and England battled for nearly 200 years to control this sun-kissed island. Wayfarers arriving these days have less nefarious plans and want only to preside over St. Lucia's legendary natural wonders and eco-adventures. Choose a heart-thumping hike up the Pitons—named a UNESCO World Heritage Site in 2004—or a treetop tram ride over the flower- and bird-filled rain forest. Humdrum may be hard to find, but there are plenty of warm welcomes from friendly locals. The island's eclectic culture and history are shared daily through the Creole patois spoken in markets and on street corners, in the French names of colorful fishing villages and in savory recipes infused with African, French and Carib heritage. And have we mentioned the sublime sunsets? Some Caribbean islands really do have it all.
Castries, Saint Lucia
Day Mayreau, St. Vincent Grenadines
Arrive 7:00 AM, Depart 6:00 PM
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
Mayreau, St. Vincent Grenadines
Day St. George's, Grenada
Arrive 8:00 AM, Depart 10:00 PM
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
St. George's, Grenada
Day Bequia, St. Vincent & the Grenadines
Arrive 8:00 AM, Depart 5:00 PM
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
Bequia, St. Vincent & the Grenadines
Day Anse Mitan, Martinique
Arrive 8:00 AM, Depart 6:00 PM
Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.
Anse Mitan, Martinique
Day Les Saintes, Guadeloupe
Arrive 8:00 AM, Depart 5:00 PM
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
Les Saintes, Guadeloupe
Day Gustavia, Saint Barthelemy
Arrive 8:00 AM, Depart 10:00 PM
"St. Barts, a French territory in the Caribbean's Leeward Islands, is the ultimate jet-set beach destination. Its 14 pristine beaches are jewels set in sparkling waters, the cuisine is infused with a French flair and the scene is cosmopolitan chic. Other islands in the region might be casual and laid-back, but here the dress code is stylish caftans, oversize sunglasses and sky-high heels. And the preferred mode of transportation is the yacht. Gustavia, the capital and main port of St. Barts (also spelled St. Barths), embodies the island's international appeal. A former fishing village, it was named for King Gustav III of Sweden—the Swedes occupied the island in the early 19th century, leaving a legacy of names and sites. The town's winding streets are lined with high-end boutiques, excellent restaurants and plenty of bars where you can toast your visit with a glass of refreshing rosé. A handful of historic sites, including forts and a lighthouse, add to the attractions. "
Gustavia, Saint Barthelemy
Day Philipsburg, Sint Maarten
Arrive 6:00AM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
 
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