Windward Ways & Tobago Cays

 
Bridgetown to Oranjestad
Fri Dec 4, 2026 - Sat Dec 12, 2026,
 8 days
 on Star Legend
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Starting from $2,999 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
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Fri Dec 4
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
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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: 
5 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.
5 Shore Excursions Available
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_
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, 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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Tue Dec 8
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 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.