Star Collector: Captivating Caribbean
 
Bridgetown to Oranjestad
Sun Jan 18, 2026 - Sun Feb 1, 2026,
 14 days
 on Wind Surf
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Starting from $4,599 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
Expand
Sun Jan 18
Bridgetown
Arrive:
Depart:6:00 PM
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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Mon Jan 19
Anse Mitan
Arrive:9:00 AM
Depart:11:00 PM
Watersports Platform: 
4 Available
+_
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.
4 Shore Excursions Available
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Anse Mitan, VIP Experience at La Mauny Plantation and Rum TastingConcierge Collection | Culture | Refreshments
Duration3.5 Hours
Activity LevelEasy-Moderate
$259
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Anse Mitan, Kayaking Mangrove DiscoveryBoating | Essentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelModerate-Strenuous
$139
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Anse Mitan, Southern Panoramic MartiniqueCulture | Sightseeing | Refreshments
Duration3.75 Hours
Activity LevelModerate
$149
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Anse Mitan, Creole VillageCulture | Essentials Collection | Sightseeing | Walking
Duration2.75 Hours
Activity LevelModerate-Strenuous
$99
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Tue Jan 20
Castries
Arrive:8:00 AM
Depart:4:00 PM
Watersports Platform: 
8 Available
+_
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.
8 Shore Excursions Available
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Castries, Concierge Collection: Half Day Private Sedan with Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$399
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Castries, Concierge Collection: Half Day Private Van with Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$499
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Castries, Concierge Collection: Lets Make Chocolate Refreshments | Culture | Concierge Collection
Duration2.5 Hours
Activity LevelEasy-Moderate
$129
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Castries, Heritage Highlights Culture | Sightseeing | Essentials Collection
Duration3.5 Hours
Activity LevelModerate
$69
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Castries, Panoramic St. LuciaEssentials Collection | Sightseeing | Refreshments
Duration3 Hours
Activity LevelModerate
$69
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Castries, Catamaran Cruise to the Pitons Outdoors | Refreshments | Sightseeing | Boating | UNESCO | Essentials Collection
Duration4 Hours
Activity LevelEasy
$149
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Castries, St. Lucian Walking Food TourCulture | Essentials Collection | Sightseeing | Refreshments | Walking
Duration3.5 Hours
Activity LevelEasy-Moderate
$189
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Castries, Rainforest Canopy Zip Line Adventure Outdoors | Wildlife | Essentials Collection
Duration4 Hours
Activity LevelStrenuous
$119
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Tue Jan 20
Pigeon Island
Arrive:6:00 PM
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.
Wed Jan 21
Pigeon Island
Arrive:
Depart:6:00 PM
Watersports Platform: 
12 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.
12 Shore Excursions Available
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Pigeon Island, Concierge Collection: Full Day Private Car & Guide Sightseeing | Concierge Collection
Duration8 Hours
Activity LevelEasy
$699
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Pigeon Island, Concierge Collection: Full Day Private Van & Guide Sightseeing | Concierge Collection
Duration8 Hours
Activity LevelEasy
$899
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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, Mt. Pimard Nature Trail & HikeEssentials Collection | Hiking | Sightseeing
Duration2.5 Hours
Activity LevelModerate
$109
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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, Off Road Segway Adventure Outdoors | Refreshments | Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$149
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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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Thu Jan 22
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 Highlights Outdoors | Wildlife | Culture | Sightseeing | Essentials Collection
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 BequiaCulture | Dining | Essentials Collection | Refreshments
Duration3.5 Hours
Activity LevelEasy-Moderate
$149
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Fri Jan 23
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
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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 Jan 24
St. George's
Arrive:7:00 AM
Depart:2:00 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
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St. Georges, Certified One-Tank Dive Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration3.5 Hours
Activity LevelStrenuous
$209
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St. Georges, Certified Two-Tank Dive Outdoors | Wildlife | Refreshments | Boating | Essentials Collection
Duration4.25 Hours
Activity LevelStrenuous
$309
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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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Concierge Collection: Farm to Table Homestead Cooking Tour (Easy-Moderate)Concierge Collection | Culture | Dining
Duration3.5 Hours
Activity LevelEasy-Moderate
$139
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St. Georges, Discover Scuba Outdoors | Watersports | Essentials Collection
Duration4.5 Hours
Activity LevelStrenuous
$279
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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, Adventure River Tubing Watersports | Wildlife | refreshment | Essentials Collection
Duration3 Hours
Activity LevelModerate
$69
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St. Georges, Sailing Cruise to the Statue ParkBoating | Essentials Collection | Refreshments | Snorkeling
Duration3.5 Hours
Activity LevelModerate-Strenuous
$89
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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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Sun Jan 25
Bridgetown
Arrive:6:00 AM
Depart:6:00 PM
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
+
_
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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Mon Jan 26
Man-O-War Bay
Arrive:8:00 AM
Depart:5:00 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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Tue Jan 27
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 Jan 28
Soufriere
Arrive:8:00 AM
Depart:4:00 PM
Watersports Platform: 
5 Available
+_
Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.
5 Shore Excursions Available
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Soufriere, Chocolate Heritage tour at Fond Doux Estate Sightseeing | Walking | Refreshments | Essentials Collection
Duration2.5 Hours
Activity LevelEasy-Moderate
$99
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Soufriere, Green Haven Organic Farm to Table LunchCulture | Dining | Essentials Collection | Sightseeing
Duration3 Hours
Activity LevelEasy-Moderate
$129
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Soufriere, Botanical Gardens, Toraille Waterfall & Beach Sightseeing | Beach | Essentials Collection
Duration4 Hours
Activity LevelEasy-Moderate
$69
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Soufriere, Snorkel at Marine Park Snorkeling | Boating | Wildlife | Essentials Collection
Duration2.5 Hours
Activity LevelModerate-Strenuous
$109
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Soufriere, Concierge Collection: Taste of St. Lucia Dining | Culture | Concierge Collection
Duration2.5 Hours
Activity LevelEasy-Moderate
$179
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Thu Jan 29
AT SEA
Arrive:
Depart:
Watersports Platform: 
Fri Jan 30
Kralendijk
Arrive:1:00 PM
Depart:10:00 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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Sat Jan 31
Willemstad
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
6 Available
+_
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.
6 Shore Excursions Available
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Willemstad, Caves and City TourCulture | Essentials Collection | Sightseeing | UNESCO | Walking
Duration2.75 Hours
Activity LevelStrenuous
$89
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Willemstad, Panoramic TourCulture | Essentials Collection | Sightseeing | Refreshments
Duration4 Hours
Activity LevelEasy
$49
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Willemstad, Day at Corendon Mangrove Beach Resort With LunchBeach | Essentials Collection | Outdoors | Refreshments
Duration5 Hours
Activity LevelEasy-Moderate
$159
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Willemstad, Walking TourEssentials Collection | Sightseeing | Walking
Duration1.5 Hours
Activity LevelModerate-Strenuous
$39
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Willemstad, Off Road Adventures in the Wild WestCulture | Essentials Collection | Sightseeing
Duration4 Hours
Activity LevelEasy-Moderate
$89
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Willemstad, Naural Wonders with SnackBeach | Culture | Essentials Collection | Sightseeing | Refreshments | Walking
Duration5 Hours
Activity LevelModerate-Strenuous
$149
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Sun Feb 1
Oranjestad
Arrive:6:00 AM
Depart:
Watersports Platform: 
1 Available
+_
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.
1 Shore Excursion Available
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Oranjestad, Aruba Island Exploration Tour with Airport Transfer Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelEasy
$135
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