Windstar Cruise

21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]

21 Days - Star Collector: A Lesser Antilles Odyssey [Philipsburg, St. Maarten to Bridgeto]
Starting from $6,199*

Philipsburg, St. Maarten to Bridgetown

Ship: Wind Surf / Wind Spirit

Departure Date : Jan 04 2026 | Feb 21 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 Falmouth Harbour, Antigua
Arrive 08:00 AM Depart 06:00 PM
It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches to midnight to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
Falmouth Harbour, Antigua
Day Road Bay, Anguilla
Arrive 08:00 AM Depart 06:00 PM
Anguilla’s name is based on the word for eel in several Romance languages, and its 17-mile length and three-mile width are appropriate to the analogy. The northernmost of the Leeward Islands chain, it is a British overseas territory. With its resources largely limited to an abundance of breathtaking beaches and coral reefs, the island’s main industries are tourism and the lucrative cultivation of offshore banking and insurance tax havens. Road Bay and its village of Sandy Ground comprise the main harbor for ships on the island, although the entire coastline is scalloped with lovely coves and anchorages that make it a magnet for yachtsmen. The official currency is the Eastern Caribbean dollar, although U.S. dollars are widely accepted. They might be well-spent on a luncheon of impeccably fresh seafood from the surrounding seas. There are no less than seven shipwrecks strewn along the island’s barrier reefs, which have made it the wreck-diving capital of the region.
Road Bay, Anguilla
Day Soper's Hole, Tortola, B.V.I. / Jost Van Dyke, Great Harbour, B.V.I.
Arrive 08:00 AM Depart 06:00 PM, Arrive 07:00PM
Arrive at the boardwalk of Pusser’s Landing and mingle with other yachtsmen in the utterly charming marina at Soper’s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port’s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through “The Narrows.”

Jost Van Dyke, Great Harbour, B.V.I.

For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
Soper's Hole, Tortola, B.V.I. / Jost Van Dyke, Great Harbour, B.V.I.
Day Jost Van Dyke, Great Harbour, B.V.I.
Depart 10:00 PM
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
Jost Van Dyke, Great Harbour, B.V.I.
Day Virgin Gorda, Prickly Pear Beach, B.V.I
Arrive 08:00 AM Depart 05:00 PM
A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
Virgin Gorda, Prickly Pear Beach, B.V.I
Day Gustavia, Saint Barthelemy
Arrive 08:00 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 06:00 AM Depart 07:00 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 Basseterre, St. Kitts
Arrive 07:00 AM Depart 10:00 PM
St. Kitts and Nevis are a pair of islands that form a single Eastern Caribbean nation. Ripe with historical sites, the larger St. Kitts passed hands among the Spanish, French and English, with the latter establishing the strongest foothold. The architecture and layout of its capital city, Basseterre, are all typically British. And the island's sprawling, colonial-era plantations are a reminder of the tumultuous history of the tobacco, rum, sugar and slave trades that were here for generations. Beyond its rich past, St. Kitts offers golden-sand beaches for relaxing, a lush jungle interior that welcomes heart-pumping adventure, laid-back bars with fantastic sunset views and restaurants serving up über-local fare.
Basseterre, St. Kitts
Day Little Bay, Montserrat, BWI
Arrive 08:00 AM Depart 06:00 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 Gustavia, Saint Barthelemy
Arrive 08:00 AM Depart 11:00 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 Deshaies, Guadeloupe
Arrive 12:30 PM Dep 10:00PM
On the west coast of the island of Basse-Terre, two kilometres north of the village of Deshaies, lies the huge and famous Grand Anse beach. Nestled in a green setting, this magnificent golden, sandy beach is the longest in Guadeloupe! It has more than a kilometre of fine sand, to the delight of sunbathers, and a multitude of coconut palms and sea grape bushes whose shade is most appreciated when it's time for a nap, a picnic lunch or a taste of handmade coconut sorbet, while admiring the waves of the Caribbean Sea lapping against the shore... It is a nice place to swim.
Deshaies, Guadeloupe
Day Roseau, Dominica
Arrive 08:00 AM Dep 5:00PM
"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 Pigeon Island, St. Lucia
Arrive 07:00 AM Dep 4:00PM
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
Pigeon Island, St. Lucia
Day Bridgetown, Barbados
Arrive 05:00 AM Dep 6:00PM
"Barbadians, or Bajans in local parlance, consider their island nation the most British of the Caribbean: Queen Elizabeth II is still head of state, and English products are stocked in many of its stores and restaurants. Barbados is known as the birthplace of international pop star Rihanna, but it has also produced some of the biggest Caribbean calypso and soca music stars. The summer Crop Over festival is a huge carnival event. With live music and crafts for sale, the popular Friday fish fry at Oistins Bay is a fun place to mingle with the locals. Centered around a waterway called the Careenage and its handsome Chamberlain Bridge, the historic center of Bridgetown, the country's capital, was granted UNESCO World Heritage status in 2011 for its wealth of British colonial architecture dating from the 17th, 18th and 19th centuries. Among the famous figures who visited Bridgetown when it was at its peak was none other than George Washington, who spent two months in 1751 in a house that still stands today, on his only trip abroad."
Bridgetown, Barbados
Day Anse Mitan, Martinique
Arrive 09:00 AM Dep 11:00PM
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 Castries, St. Lucia / Pigeon Island, St. Lucia
Arrive 08:00 AM Dep 4:00PM, Arrive 6:00PM
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.

Pigeon Island, St. Lucia

The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
Castries, St. Lucia / Pigeon Island, St. Lucia
Day Pigeon Island, St. Lucia
Depart 6:00 PM
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
Pigeon Island, St. Lucia
Day Bequia, St. Vincent & the Grenadines
Arrive 08:00 AM Depart 10:00 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 Mayreau, St. Vincent Grenadines
Arrive 08:00 AM Depart 06:00 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 07:00 AM Dep 2:00PM
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 Bridgetown, Barbados
Arrive 06:00 AM
"Barbadians, or Bajans in local parlance, consider their island nation the most British of the Caribbean: Queen Elizabeth II is still head of state, and English products are stocked in many of its stores and restaurants. Barbados is known as the birthplace of international pop star Rihanna, but it has also produced some of the biggest Caribbean calypso and soca music stars. The summer Crop Over festival is a huge carnival event. With live music and crafts for sale, the popular Friday fish fry at Oistins Bay is a fun place to mingle with the locals. Centered around a waterway called the Careenage and its handsome Chamberlain Bridge, the historic center of Bridgetown, the country's capital, was granted UNESCO World Heritage status in 2011 for its wealth of British colonial architecture dating from the 17th, 18th and 19th centuries. Among the famous figures who visited Bridgetown when it was at its peak was none other than George Washington, who spent two months in 1751 in a house that still stands today, on his only trip abroad."
Bridgetown, Barbados
 
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