17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]
![17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]](/images/packages/extraimages/7138_2026-sc_round_trip_philipsburg_1_14_2026.jpg "17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]")
Itinerary
Day Philipsburg, Sint MaartenDepart 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."
"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, BWIArrive 08:00 AM Depart 05:00 PM
Today we visit Pompeii of the Caribbeanan island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isnt intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
Today we visit Pompeii of the Caribbeanan island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isnt intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
Day Roseau, DominicaArrive 08:00 AM Depart 06:00 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. "
"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. "
Day Castries, Saint LuciaArrive 08:00 AM Depart 08:00 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 seathough 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 Pitonsnamed a UNESCO World Heritage Site in 2004or 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.
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 seathough 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 Pitonsnamed a UNESCO World Heritage Site in 2004or 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.
Day Mayreau, St. Vincent GrenadinesArrive 07:00 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.
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.
Day St. George's, GrenadaArrive 08:00 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.
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.
Day Bequia, St. Vincent & the GrenadinesArrive 08:00 AM Depart 05:00 PM
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequias whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the islands famed model boat builders at work on their miniature masterpieces.
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequias whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the islands famed model boat builders at work on their miniature masterpieces.
Day Anse Mitan, MartiniqueArrive 08:00 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.
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.
Day Les Saintes, GuadeloupeArrive 08:00 AM Depart 05:00 PM
This is the Caribbean as youve 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.
This is the Caribbean as youve 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.
Day Gustavia, Saint BarthelemyArrive 08:00 AM Depart 10:00 PM, Arrive 7:00PM
"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 Swedenthe 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. "
"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 Swedenthe 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. "
Day Philipsburg, Sint MaartenArrive 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."
"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 Soper's Hole, Tortola, B.V.I. / Jost Van Dyke, Great Harbour, B.V.I.Arrive 08:00 AM Depart 06:00 PM, Arrive 7:00PM
Arrive at the boardwalk of Pussers Landing and mingle with other yachtsmen in the utterly charming marina at Sopers Hole. Find a deserted stretch of beach to kick back and ponder this tiny ports 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, its 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, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Arrive at the boardwalk of Pussers Landing and mingle with other yachtsmen in the utterly charming marina at Sopers Hole. Find a deserted stretch of beach to kick back and ponder this tiny ports 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, its 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, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Day Jost Van Dyke, Great Harbour, B.V.I.Depart 10:00 PM
For an island comprised of a mere eight square miles, its 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, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
For an island comprised of a mere eight square miles, its 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, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Day Virgin Gorda, Prickly Pear Beach, B.V.IArrive 07:00 AM Dep 5:00PM
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 youre free to explore.
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 youre free to explore.
Day Gustavia, Saint BarthelemyArrive 08:00 AM Dep 10:00PM
"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 Swedenthe 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. "
"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 Swedenthe 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. "
Day Road Bay, AnguillaArrive 08:00 AM Depart 06:00 PM
Anguillas 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 islands 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 islands barrier reefs, which have made it the wreck-diving capital of the region.
Anguillas 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 islands 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 islands barrier reefs, which have made it the wreck-diving capital of the region.
Day Falmouth Harbour, AntiguaArrives 08:00 AM Departs 5:00 PM
Its 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.
Its 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.
Day Philipsburg, Sint MaartenArrive 06:00 AM
"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."
"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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