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Star Collector: Caribbean Explorations
Jan 23, 2027 — Feb 6, 2027
Starting from
Complimentary All-In Package
Free Laundry for Collectors:
Reduced Deposit
PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN
14 Nights on Wind Surf
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Barbuda, Soper’s Hole in Tortola, Gustavia in St. Barthémy, St. Lucia’s Pigeon Island and much more.






Popular Highlights
Anchor alongside the pristine beaches of Pigeon Island’s 40-acre National Park and explore at your leisure.
Discover St. Lucia’s UNESCO site when you see the twin Pitons, rising majestically from the turquoise sea.
Embrace the island life on St. Kitts’ one-of-a-kind Shipwreck Beach.
Soak in the naturally-formed granite bathing pools of "The Baths" at Virgin Gorda.
Enjoy Windstar’s exclusive Signature Beach Party at Prickly Pear Beach.
Overnight in Jost Van Dyke for more in-depth exploration.
Pack light with complimentary daily laundry service.

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.
Available Excursions
Philipsburg, St. Maarten
Time
10:00 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$189
Philipsburg, St. Maarten
Time
8:30 AMDuration
4.5 HoursActivity Level
Easy-ModerateAdd during booking
$99
Philipsburg, St. Maarten
Time
10:00 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$189
Philipsburg, St. Maarten
Time
7:30 AMDuration
4.5 HoursActivity Level
EasyAdd during booking
$99
Philipsburg, St. Maarten
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$639

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney's Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.
Available Excursions
Charlestown
Time
8:30 AMDuration
2.5 HoursActivity Level
StrenuousAdd during booking
$159
Charlestown
Time
8:30 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$479
Charlestown
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$85
Charlestown
Time
8:30 AMDuration
5 HoursActivity Level
Moderate-StrenuousAdd during booking
$99
Charlestown
Time
10:00 AMDuration
3.5 HoursActivity Level
Easy-ModerateAdd during booking
$69
Charlestown
Time
8:30 AMDuration
2.5 HoursActivity Level
StrenuousAdd during booking
$309

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.
Available Excursions
Roseau
Time
12:15 PMDuration
3 HoursActivity Level
StrenuousAdd during booking
$89
Roseau
From cacao pod to chocolate and rum distillery — a rich, hands-on taste of Dominica's plantation heritage in one afternoon.
Time
8:30 AMDuration
4.5 HoursActivity Level
EasyAdd during booking
$229
Roseau
Time
10:00 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Roseau
Time
8:30 AMDuration
4 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Roseau
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$99
Roseau
Time
8:30 AMDuration
4.5 HoursActivity Level
StrenuousAdd during booking
$159
Roseau
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$89
Roseau
Time
10:00 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$139
Roseau
Time
8:30 AMDuration
5.5 HoursActivity Level
StrenuousAdd during booking
$225
Roseau
Time
8:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$79
Roseau
Time
10:30 AMDuration
4.5 HoursActivity Level
Easy-ModerateAdd during booking
$109
Roseau
Time
9:00 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$159

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

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.
Available Excursions
Les Saintes
Time
12:30 PMDuration
2 HoursActivity Level
StrenuousAdd during booking
$149
Les Saintes
Time
12:30 PMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$179
Les Saintes
Time
12:30 PMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$269
Les Saintes
Time
12:30 PMDuration
1 HoursActivity Level
EasyAdd during booking
$129

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.
Available Excursions
Basseterre
Time
1:00 PMDuration
3.25 HoursActivity Level
Moderate-StrenuousAdd during booking
$119
Basseterre
Time
9:00 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$99
Basseterre
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$129
Basseterre
Time
10:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$69
Basseterre
Time
9:00 AMDuration
3.25 HoursActivity Level
Easy-ModerateAdd during booking
$89
Basseterre
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$139
Basseterre
Time
9:00 AMDuration
3.5 HoursActivity Level
EasyAdd during booking
$99

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.
Available Excursions
Gustavia
Dive into St. Barth’s Protected Marine Reserve and discover vibrant reefs, colorful marine life, and crystal-clear waters.
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$359
Gustavia
Enjoy an exclusive island panorama tour — explore local highlights at your pace with a private driver and guide!
Time
8:30 AMDuration
1 HoursActivity Level
EasyAdd during booking
$149
Gustavia
Savor Gustavia’s French-Caribbean flavors with crêpes, Le Select, gourmet bites & Champagne as you explore the town.
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$369
Gustavia
Jet ski from Gustavia to Shell, Gouverneur & Salines beaches, then swim in the crystal-clear waters near Coco Island.
Time
8:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$529
Gustavia
Leisurely sail St. Barth’s coast to crystal-clear waters of Colombier Beach, relax in crystal waters & spot colorful marine life.
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$319
Gustavia
Toast the sunset aboard a sailing catamaran, cruise Gustavia Harbor & admire mega yachts with Champagne and scenic views.
Time
5:00 PMDuration
1.5 HoursActivity Level
Easy-ModerateAdd during booking
$209
Gustavia
Dive St. Barth’s Protected Marine Reserve and discover vibrant coral reefs, tropical fish, and incredible marine life.
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$499
Gustavia
Explore the island at your own pace with a self-drive adventure through lush countryside and scenic hidden gems.
Time
8:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$359
Gustavia
Relax at Le Barthélemy Resort — unwind on a stunning St. Barts beach, swim, savor lunch, and enjoy luxury by the sea.
Time
8:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$579

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.
Available Excursions
Philipsburg, St. Maarten
Time
8:30 AMDuration
4.5 HoursActivity Level
Easy-ModerateAdd during booking
$99
Philipsburg, St. Maarten
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$639
Philipsburg, St. Maarten
Time
7:30 AMDuration
4.5 HoursActivity Level
EasyAdd during booking
$99
Philipsburg, St. Maarten
Time
9:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$169
Philipsburg, St. Maarten
Time
10:00 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$189
Philipsburg, St. Maarten
Time
7:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$189

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.
Available Excursions
Road Bay
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$219
Road Bay
Time
8:30 AMDuration
4 HoursActivity Level
EasyAdd during booking
$139
Road Bay
Time
9:00 AMDuration
2.5 HoursActivity Level
StrenuousAdd during booking
$599
Road Bay
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$339

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.
Available Excursions
Soper's Hole
Time
8:30 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$109
Soper's Hole
Time
8:30 AMDuration
3 HoursActivity Level
Moderate-StrenuousAdd during booking
$149
Soper's Hole
Time
8:30 AMDuration
4 HoursActivity Level
ModerateAdd during booking
$199
Soper's Hole
Time
8:30 AMDuration
4.5 HoursActivity Level
EasyAdd during booking
$119

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.

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.
Available Excursions
Jost Van Dyke, Great Harbour
Time
8:30 AMDuration
4.5 HoursActivity Level
Moderate-StrenuousAdd during booking
$259

The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns
Available Excursions
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:00 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$99
Virgin Gorda / Prickly Pear, British Virgin Islands
Time
8:30 AMDuration
2.75 HoursActivity Level
Moderate-StrenuousAdd during booking
$299

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.
Available Excursions
Gustavia
Toast the sunset aboard a sailing catamaran, cruise Gustavia Harbor & admire mega yachts with Champagne and scenic views.
Time
5:00 PMDuration
1.5 HoursActivity Level
Easy-ModerateAdd during booking
$209
Gustavia
Leisurely sail St. Barth’s coast to crystal-clear waters of Colombier Beach, relax in crystal waters & spot colorful marine life.
Time
8:30 AMDuration
3 HoursActivity Level
ModerateAdd during booking
$319
Gustavia
Dive into St. Barth’s Protected Marine Reserve and discover vibrant reefs, colorful marine life, and crystal-clear waters.
Time
8:30 AMDuration
3 HoursActivity Level
StrenuousAdd during booking
$359
Gustavia
Explore the island at your own pace with a self-drive adventure through lush countryside and scenic hidden gems.
Time
8:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$359
Gustavia
Dive St. Barth’s Protected Marine Reserve and discover vibrant coral reefs, tropical fish, and incredible marine life.
Time
8:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$499
Gustavia
Relax at Le Barthélemy Resort — unwind on a stunning St. Barts beach, swim, savor lunch, and enjoy luxury by the sea.
Time
8:30 AMDuration
6 HoursActivity Level
Easy-ModerateAdd during booking
$579
Gustavia
Enjoy an exclusive island panorama tour — explore local highlights at your pace with a private driver and guide!
Time
8:30 AMDuration
1 HoursActivity Level
EasyAdd during booking
$149
Gustavia
Jet ski from Gustavia to Shell, Gouverneur & Salines beaches, then swim in the crystal-clear waters near Coco Island.
Time
8:30 AMDuration
2 HoursActivity Level
StrenuousAdd during booking
$529
Gustavia
Savor Gustavia’s French-Caribbean flavors with crêpes, Le Select, gourmet bites & Champagne as you explore the town.
Time
8:30 AMDuration
2.5 HoursActivity Level
ModerateAdd during booking
$369

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 into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
Available Excursions
Falmouth Harbour
Time
12:15 PMDuration
3 HoursActivity Level
ModerateAdd during booking
$129
Falmouth Harbour
Time
9:30 AMDuration
4 HoursActivity Level
StrenuousAdd during booking
$149
Falmouth Harbour
Time
8:45 AMDuration
2 HoursActivity Level
Easy-ModerateAdd during booking
$149
Falmouth Harbour
Time
10:00 AMDuration
4 HoursActivity Level
EasyAdd during booking
$99
Falmouth Harbour
Time
9:00 AMDuration
3 HoursActivity Level
Easy-ModerateAdd during booking
$89

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.
Staterooms