Bermuda Bliss

 
Boston to San Juan
Fri Oct 22, 2027 - Mon Nov 1, 2027,
 10 days
 on Star Pride
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Boston to San Juan
Embark on a voyage from the East Coast to San Juan with an overnight in St. George’s, Bermuda. Indulge in the luxury of multiple sea days, where you’ll have uninterrupted relaxation. Explore the UNESCO World Heritage Site of St. George’s, Bermuda.  Take in the charming streets lined with colonial buildings, visit the iconic St. Peter's Church, one of the oldest Anglican churches in the Western Hemisphere, and discover the fascinating history at the Bermuda National Trust Museum. For nature enthusiasts, St. George's offers stunning coastal views, and Tobacco Bay provides an opportunity for snorkeling in crystal-clear waters teeming with marine life. Arrive in the historic and vibrant city of San Juan, Puerto Rico. Traverse the cobblestone streets of Old San Juan, visit ancient forts, and immerse yourself in the rich local culture. From colonial charm to lively markets, San Juan welcomes you with a blend of history and Caribbean flair.
voyage map
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Day 1: Boston
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.
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Day 4: Hamilton
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.
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Day 5: Hamilton
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.
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Day 5: St. George's
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.
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Day 6: St. George's
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.
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Day 9: Gustavia
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
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Day 10: Virgin Gorda / Prickly Pear, British Virgin Islands
  • The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
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Day 11: San Juan
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.
Popular Highlights
Bridge
Dropping by the Bridge for an impromptu navigation lesson.
Ocean Vistas
Sweeping ocean vistas from your stateroom or suite.
El Morro
Have your camera ready for the incredible views from El Morro, San Juan’s UNESCO site
Stars
More stars overhead than you’ve ever imagined.
self-care
Spend time on self-care, whether it’s reading a book or relaxing in the complimentary thermal suite.
 
St. George
Overnight in UNESCO site St. George’s with its famous pink-sand beaches and 18th century Town Hall
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Fri Oct 22
Boston
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Sat Oct 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Oct 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Oct 25
Hamilton
Arrive:  8:45 AM
Depart:  
Watersports Platform: 
Tue Oct 26
Hamilton
Arrive:  
Depart:  7:00 AM
Watersports Platform: 
Tue Oct 26
St. George's
Arrive:  10:00 AM
Depart:  
Watersports Platform: 
Wed Oct 27
St. George's
Arrive:  
Depart:  12:00 PM
Watersports Platform: 
Thu Oct 28
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Oct 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Oct 30
Gustavia
Arrive:  10:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sun Oct 31
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Nov 1
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Marina
*Select voyages
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Fri, Oct 22 - Mon, Nov 1, 2027
STAR PRIDE
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