Star Collector: A Lesser Antilles Odyssey

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Port to Port Philipsburg to Bridgetown

Departure date / Duration 21st February 2026, 22 nights

Yacht Name Wind Spirit

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Itinerary

Embrace extraordinary experiences exclusive to small ship cruising during this three-week exploration of the Caribbean’s Lesser Antilles island chain. Swim with dolphins during an extended overnight stay in Jost Van Dyke in the British Virgin Islands. Savor African, European, and Indian ingredients and influences in popular Caribbean dishes as you sample spicy regional cuisine in the Fairview Great House on St. Kitts. Tour the Montserrat Volcano Observatory and learn how plant and animal life recover after volcanic eruptions, then see firsthand at the Montserrat National Trust Amerindian Gardens near Little Bay. Float above colorful coral reefs in clear-bottom kayaks as you glide through the pristine blue waters of Les Saintes on Guadeloupe. Hang onto halyards and winch handles as you master sailing a 40-foot racing yacht on scenic Rodney’s Bay near Pigeon Island on St. Lucia. Wander the 18th century grounds of the childhood home of Empress Josephine, Napoleon’s future wife, as you uncover historic French colonial life on Martinique.

Day to Day Itinerary

Date	Country	Port
Day 1	Sint Maarten (Dutch part)	Philipsburg
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Day 3	Anguilla	Road Bay
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
Day 4	British Virgin Islands	Sopers Hole, Tortola
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 romantic sunset Sail Away.
Day 5	British Virgin Islands	Sopers Hole, Tortola
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 romantic sunset Sail Away.
Day 6	British Virgin Islands	Great Harbour, Jost Van Dyke
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.
Day 7	Saint Barthélemy	Gustavia
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
Day 8	Sint Maarten (Dutch part)	Philipsburg
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
Day 9	Saint Kitts and Nevis	Basseterre, Saint Kitts
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
Day 10	Saint Barthélemy	Gustavia
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
Day 12	Guadeloupe	Terre-de-Haut
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.
Day 13	Dominica	Roseau
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site.
Day 14	Saint Vincent and the Grenadines	Mayreau Island
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 15	Barbados	Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.
Day 17	Saint Kitts and Nevis	Basseterre, Saint Kitts
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
Day 19	Guadeloupe	Terre-de-Haut
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.
Day 20	Dominica	Roseau
Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you're up for an optional hike, don't miss Boiling Lake and the Valley of Desolation at Dominica's Morne Trois Pitons National Park, a UNESCO World Heritage Site.
Day 21	Saint Vincent and the Grenadines	Mayreau Island
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 22	Martinique	Trois-Ilets
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 23	Barbados	Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.