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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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New York City to San Juan
Embark on a 7-day ocean crossing from Manhattan to San Juan with an overnight in St. George’s, Bermuda. Commence your cruise adventure amid the iconic skyline of Manhattan, absorbing the grandeur of the Statue of Liberty and the Brooklyn Bridge. Indulge in the bliss of multiple sea days, where you’ll have uninterrupted relaxation. As you traverse the cobblestone streets of St. George, Bermuda, a UNESCO World Heritage Site, the vibrant hues of pastel-colored buildings evoke a sense of timeless charm. Immerse yourself in the rich tapestry of culture and history, from the imposing silhouette of St. Peter's Church to the architectural marvel of the Town Hall. Gaze upon the crystal-clear waters surrounding Bermuda, and you'll discover a serenity that rejuvenates the soul during an overnight before a few more tranquil days at sea. Arrive in the historic and vibrant city of San Juan, Puerto Rico, a city welcoming  you with a blend of history and Caribbean flair.
voyage map
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Day 1: New York City
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.
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Day 4: 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 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 8: 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.
days at sea
Spend relaxing days at sea with time for making new friends, lounging on deck, and attending onboard enrichment programs.
El Morro
Have your camera ready for the incredible views from El Morro, San Juan’s UNESCO site
Manhattan
Conveniently depart from iconic Manhattan and don’t miss our Signature Sail Away event.
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
Suite Happy Hour
Stretch out in your spacious suite and stay in for a private happy hour.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sun Oct 19
New York City
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
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: 
Thu Oct 23
St. George's
Arrive:  
Depart:  12:00 PM
Watersports Platform: 
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: 
Star Pride
Carrying only 312 guests, Star Pride still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure! Learn more about the newly renovated ship and the $250 Million Star Plus Initiative.
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Accommodations & Pricing
This all-suite ship completed renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love.
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
Watersports Platform
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 beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Oct 19 - Sun, Oct 26, 2025
STAR PRIDE
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