Star Collector: Captivating Caribbean

 
Bridgetown to Oranjestad
Fri Nov 27, 2026 - Sat Dec 12, 2026,
 15 days
 on Star Legend
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Starting from $4,099 USD
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ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

Date
Port
Arrive
Depart
Marina
Shore
Excursions
Expand
Fri Nov 27
Bridgetown
Arrive:
Depart:6:00 PM
Watersports Platform: 
3 Available
+_
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.
3 Shore Excursions Available
+
_
Bridgetown: Barbados Island Tour with Airport Transfer Dining | Sightseeing | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
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Bridgetown, Bajan Rum and Beer Tour with Transfer to Airport
Duration3.5 Hours
Activity Level
$219
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Bridgetown, Bajan Rum and Beer Tour with Transfer to Windstar Hotel
Duration3.5 Hours
Activity Level
$219
VIEW DETAILS
Sat Nov 28
Anse Mitan
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
+_
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.
Sun Nov 29
Pigeon Island
Arrive:8:00 AM
Depart:
Watersports Platform: 
+_
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.
Mon Nov 30
Pigeon Island
Arrive:
Depart:6:00 AM
Watersports Platform: 
+_
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.
Mon Nov 30
Castries
Arrive:8:00 AM
Depart:3:00 PM
Watersports Platform: 
+_
The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city’s historic buildings were destroyed in major fires between 1785 and 1948 but you’ll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.
Mon Nov 30
The Pitons
Arrive:5:30 PM
Depart:6:30 PM
Watersports Platform: 
+_
Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.
Tue Dec 1
Mayreau
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
1 Available
+_
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.
1 Shore Excursion Available
+
_
Mayreau, Grenadines Island Escape Snorkeling | Outdoors | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$89
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Wed Dec 2
St. George's
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
10 Available
+_
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.
10 Shore Excursions Available
+
_
St. Georges, Fort Frederick Rainforest & WaterfallSightseeing | Refreshments
Duration3.5 Hours
Activity LevelModerate
$99
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St. Georges, Certified One-Tank DiveBoating | Essentials Collection | Outdoors | Refreshments | Wildlife
Duration3.5 Hours
Activity LevelStrenuous
$215
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St. Georges, Certified Two-Tank DiveBoating | Essentials Collection | Outdoors | Refreshments | Wildlife
Duration4.25 Hours
Activity LevelStrenuous
$319
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St. Georges, Clear Bottom Kayaking Watersports | Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate
$89
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St. Georges, Discover Scuba Outdoors | Watersports | Essentials Collection
Duration4.5 Hours
Activity LevelStrenuous
$279
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St. Georges, The Best of GrenadaDining | Essentials Collection | Outdoors | Sightseeing | Wildlife
Duration7.5 Hours
Activity LevelEasy
$169
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St. Georges, Powerboat & Snorkeling at the Statues Park *Boating | Essentials Collection | Sightseeing | Snorkeling
Duration2 Hours
Activity LevelModerate-Strenuous
$119
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St. Georges, Sailing Cruise to the Statue ParkBoating | Essentials Collection | Refreshments | Snorkeling
Duration3.5 Hours
Activity LevelModerate-Strenuous
$99
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St Georges, Spice of Our LivesCulture | Essentials Collection | Sightseeing | Refreshments
Duration4 Hours
Activity LevelEasy-Moderate
$69
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St. Georges, Izzie's Great House DiscoveryCulture | Dining | Essentials Collection
Duration3 Hours
Activity LevelEasy-Moderate
$119
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Thu Dec 3
Bequia
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
6 Available
+_
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.
6 Shore Excursions Available
+
_
Bequia, Bequia Fort & Lower Beach Getaway *Beach | Essentials Collection | Refreshments
Duration3 Hours
Activity LevelEasy-Moderate
$99
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Bequia HighlightsCulture | Essentials Collection | Outdoors | Sightseeing | Wildlife
Duration2.5 Hours
Activity LevelEasy-Moderate
$89
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Bequia, Concierge Collection: Rum Tasting at Firefly Plantation
Duration3 Hours
Activity LevelModerate
$165
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Bequia, Mustique Magic with Lunch Dining | Sightseeing | Boating | Essentials Collection
Duration6 Hours
Activity LevelModerate
$269
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Bequia Snorkel Adventure Snorkeling | Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$119
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Bequia, Taste of BequiaConcierge Collection | Culture | Dining | Essentials Collection | Refreshments
Duration3.5 Hours
Activity LevelEasy-Moderate
$149
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Fri Dec 4
Bridgetown
Arrive:5:00 AM
Depart:6:00 PM
Watersports Platform: 
3 Available
+_
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.
3 Shore Excursions Available
+
_
Bridgetown: Barbados Island Tour with Airport Transfer Dining | Sightseeing | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
VIEW DETAILS
Bridgetown, Bajan Rum and Beer Tour with Transfer to Airport
Duration3.5 Hours
Activity Level
$219
VIEW DETAILS
Bridgetown, Bajan Rum and Beer Tour with Transfer to Windstar Hotel
Duration3.5 Hours
Activity Level
$219
VIEW DETAILS
Sat Dec 5
Rodney Bay
Arrive:3:00 PM
Depart:8:00 AM
Watersports Platform: 
+_
Rodney Bay, Saint Lucia
Sat Dec 5
The Pitons
Arrive:5:30 PM
Depart:6:30 PM
Watersports Platform: 
+_
Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.
Sun Dec 6
Scarborough, Tobago
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
+_
Scarborough, Tobago
Mon Dec 7
Bequia
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
+_
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.
Tue Dec 8
Mayreau
Arrive:8:00 AM
Depart:6:00 PM
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.
Wed Dec 9
AT SEA
Arrive:
Depart:
Watersports Platform: 
Thu Dec 10
Kralendijk
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
+_
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
Fri Dec 11
Willemstad
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
+_
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.
Sat Dec 12
Oranjestad
Arrive:6:00 AM
Depart:
Watersports Platform: 
+_
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.