Windward Ways & Tobago Cays
 
Oranjestad to Bridgetown
Sun Mar 15, 2026 - Sun Mar 22, 2026,
 7 days
 on Star Pride
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Starting from $2,599 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
Watersports
Platform
Shore
Excursions
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Sun Mar 15
Oranjestad
Arrive:
Depart:6:00 PM
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.
Mon Mar 16
Kralendijk
Arrive:8:00 AM
Depart:9:00 PM
Watersports Platform: 
6 Available
+_
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
6 Shore Excursions Available
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Kralendijk, Bonaire Glass Bottom Boat Boating | Wildlife | Essentials Collection
Duration1.5 Hours
Activity LevelEasy
$59
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Kralendijk, Kayak, Beach & SnorkelBoating | Essentials Collection | Snorkeling | Wildlife
Duration2.5 Hours
Activity LevelModerate-Strenuous
$69
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Kralendijk, Bonaire Highlights Wildlife | Refreshments | Sightseeing | Essentials Collection
Duration2.75 Hours
Activity LevelEasy
$79
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Kralendijk, Samur Sail, Beach & SnorkelBeach | Boating | Essentials Collection | Refreshments | Snorkeling
Duration3 Hours
Activity LevelModerate-Strenuous
$79
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Kralendijk, Snorkel Safari by Sustainable CatamaranBoating | Essentials Collection | Refreshments | Snorkeling | Wildlife
Duration3 Hours
Activity LevelModerate-Strenuous
$79
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Kralendijk, Kralendijk by Eco Powered Tuk-TukEssentials Collection | Sightseeing | Wildlife
Duration Hour
Activity LevelEasy
$39
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Tue Mar 17
AT SEA
Arrive:
Depart:
Watersports Platform: 
Wed Mar 18
Pigeon Island
Arrive:8:00 AM
Depart:2:30 PM
Watersports Platform: 
8 Available
+_
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.
8 Shore Excursions Available
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Pigeon Island, Aerial Tram Park Wildlife | Refreshments | Walking | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$155
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Pigeon Island, Catamaran Cruise to the PitonsBeach | Boating | Essentials Collection | Sightseeing | Refreshments | UNESCO
Duration5 Hours
Activity LevelEasy
$149
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Pigeon Island, St. Lucian Walking Food TourCulture | Essentials Collection | Sightseeing | Refreshments | Walking
Duration3.5 Hours
Activity LevelEasy-Moderate
$179
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Pigeon Island, Panoramic St. LuciaSightseeing | Refreshments
Duration3 Hours
Activity LevelEasy
$55
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Pigeon Island, Discover Sailing Boating | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$129
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Pigeon Island, Rainforest Canopy Zip Line Adventure Wildlife | Refreshments | Sightseeing | Essentials Collection
Duration4.5 Hours
Activity LevelStrenuous
$119
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Pigeon Island, Concierge Collection: Half Day Private Car & Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$399
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Pigeon Island, Concierge Collection: Half Day Private Van & Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$499
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Wed Mar 18
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.
Thu Mar 19
Bequia
Arrive:8:00 AM
Depart:10:00 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
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Bequia, Bequia Fort & Lower Beach Getaway *Beach | Essentials Collection | Refreshments
Duration3 Hours
Activity LevelEasy-Moderate
$95
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Bequia, Bequia Heritage and Scenic TouEssentials Collection | Sightseeing | 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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Fri Mar 20
Mayreau
Arrive:8:00 AM
Depart:5:00 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
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Mayreau, Grenadines Island Escape Snorkeling | Outdoors | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$89
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Sat Mar 21
Man-O-War Bay
Arrive:7:00 AM
Depart:4:00 PM
Watersports Platform: 
4 Available
+_
Listen for the sound of a conch announcing the return of the fishing boats. Bobbing next to us are flotillas of pelicans – hinting at the excellent snorkeling waiting for you here and in neighboring Pirate’s Bay.
4 Shore Excursions Available
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Man-O-War, Angel Reef by Glass Bottom Boat Wildlife | Snorkeling | Boating | Essentials Collection
Duration2.5 Hours
Activity LevelModerate
$89
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Man-O-War, Tobago Cocoa Discovery *Essentials Collection | Sightseeing | Refreshments
Duration4 Hours
Activity LevelModerate
$109
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Man-O-War, Tobago Rainforest Nature TrailEssentials Collection | Hiking | Outdoors | Wildlife
Duration5 Hours
Activity LevelStrenuous
$109
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Man-O-War, Argyle Waterfalls Hiking | Watersports | Essentials Collection
Duration4 Hours
Activity LevelModerate
$79
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Sun Mar 22
Bridgetown
Arrive:6:00 AM
Depart:
Watersports Platform: 
2 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.
2 Shore Excursions Available
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Bridgetown: Barbados Island Tour with Airport Transfer Dining | Sightseeing | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
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Bridgetown: Barbados Island Tour with Transfer to Windstar Hotel Sightseeing | Dining | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$129
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