Bermuda Bliss
 
New York City to San Juan
Sun Oct 19, 2025 - Sun Oct 26, 2025,
 7 days
 on Star Pride
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Starting from $2,399 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 Oct 19
New York City
Arrive:
Depart:6:00 PM
Watersports Platform: 
The largest city in the United States, New York City sits at the mouth of the Hudson River and is made up of five boroughs – Brooklyn, Queens, Manhattan, The Bronx and Staten Island. It is the premier gateway for immigrants, with almost 800 languages spoken there. Full of attractions, its iconic sites include the Empire State Building, Times Square, Central Park, The Museum of Modern Art, the Statue of Liberty and The Metropolitan Museum of Art to name just a few.
Mon Oct 20
AT SEA
Arrive:
Depart:
Watersports Platform: 
Tue Oct 21
AT SEA
Arrive:
Depart:
Watersports Platform: 
Wed Oct 22
St. George's
Arrive:8:00 AM
Depart:
Watersports Platform: 
5 Available
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In 2000 St. George’s was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George’s will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter’s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore’s Jungle, Cooper’s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.
5 Shore Excursions Available
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St. Georges, Crystal Caves Discovery TourEssentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelModerate
$109
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St. Georges, Colonial St. Georges Sightseeing Trip *Essentials Collection | Sightseeing | UNESCO
Duration2.5 Hours
Activity LevelEasy
$109
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St. Georges, Harrington Sound ECO Cruise *Boating | Essentials Collection | Sightseeing | Wildlife
Duration3.5 Hours
Activity LevelModerate
$199
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St. Georges, Coopers Island Ebike Adventure Tour *Beach | Biking | Essentials Collection | Sightseeing
Duration2 Hours
Activity LevelModerate-Strenuous
$149
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St. Georges, St Georges Heritage Walking Tour *Essentials Collection | Sightseeing | UNESCO | Walking
Duration1.5 Hours
Activity LevelModerate
$59
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Thu Oct 23
St. George's
Arrive:
Depart:12:00 PM
Watersports Platform: 
In 2000 St. George’s was named a UNESCO World Heritage Site, founded in 1609 by an English ship that got blown off course, Strolling the streets of St George’s will feel like a step back in time. The well-preserved buildings and fortress have made it a haven of British colonial architecture including St. Peter’s Church. Natural sites to see here in addition include Tobacco Bay Beach, Tom Moore’s Jungle, Cooper’s Island Nature Reserve, Ferry Reach National Park, and the Crystal Caves of Bermuda.
Fri Oct 24
AT SEA
Arrive:
Depart:
Watersports Platform: 
Sat Oct 25
AT SEA
Arrive:
Depart:
Watersports Platform: 
Sun Oct 26
San Juan
Arrive:8:00 AM
Depart:
Watersports Platform: 
6 Available
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The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
6 Shore Excursions Available
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San Juan: Barilito Rum Tour & Tasting with Transfer to Windstar HotelEssentials Collection | Sightseeing | Refreshments
Duration2.5 Hours
Activity LevelEasy-Moderate
$259
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San Juan: Barilito Rum Tour & Tasting with Transfer to AirportCulture | Essentials Collection | Sightseeing
Duration2.5 Hours
Activity LevelEasy-Moderate
$259
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San Juan, Concierge Collection: Half Day Private SUV with Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$829
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San Juan, Concierge Collection: Half Day Private Van with Guide Sightseeing | Concierge Collection
Duration4 Hours
Activity LevelEasy
$729
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San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Windstar Hotel Sightseeing | Essentials Collection
Duration3 Hours
Activity LevelModerate-Strenuous
$159
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San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport Sightseeing | Essentials Collection
Duration3.75 Hours
Activity LevelModerate-Strenuous
$159
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