INTERNATIONAL NUMBERS HEALTH & SAFETY YACHT CLUB WISHLIST MY WINDSTAR Call Your Travel Advisor or800.258.7245
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INTERNATIONAL NUMBERS HEALTH & SAFETY YACHT CLUB WISHLIST MY WINDSTAR
Call Your Travel Advisor or800.258.7245
Bermuda Bliss
 
Boston to San Juan
Tue Oct 20, 2026 - Wed Oct 28, 2026,
 8 days
 on Star Pride
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Starting from $2,399 USD
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OVERVIEW & ITINERARY
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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.

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Date
Port
Arrive
Depart
Watersports
Platform
Shore
Excursions
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Tue Oct 20
Boston
Arrive:
Depart:5:00 PM
Watersports Platform: 
Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.
Wed Oct 21
AT SEA
Arrive:
Depart:
Watersports Platform: 
Thu Oct 22
AT SEA
Arrive:
Depart:
Watersports Platform: 
Fri Oct 23
Hamilton
Arrive:8:45 AM
Depart:
Watersports Platform: 
The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.
Sat Oct 24
Hamilton
Arrive:
Depart:7:00 AM
Watersports Platform: 
The capital of Bermuda is the energetic heart of Bermuda. A walk along Front Street on the harbor features interesting pastel-colored colonial buildings and boutiques. Sites to see here include the Cathedral of the Most Holy Trinity, built in 1869 with a tower that displays panoramic views of the city. Find the Bermuda National Gallery and the Bermuda Aquarium, Museum and Zoo.
Sat Oct 24
St. George's
Arrive:10:00 AM
Depart:
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.
Sun Oct 25
St. George's
Arrive:
Depart:7:00 AM
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.
Mon Oct 26
AT SEA
Arrive:
Depart:
Watersports Platform: 
Tue Oct 27
AT SEA
Arrive:
Depart:
Watersports Platform: 
Wed Oct 28
San Juan
Arrive:7:00 AM
Depart:
Watersports Platform: 
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.