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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
?All-inclusive from
$2,962
?Cruise Only From
$2,339
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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.
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $2,339 per guest
? All-inclusive price from $2,962 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $2,429 per guest
? All-inclusive price from $3,052 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $2,519 per guest
? All-inclusive price from $3,142 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $2,609 per guest
? All-inclusive price from $3,232 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $2,699 per guest
? All-inclusive price from $3,322 per guest
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $2,879 per guest
? All-inclusive price from $3,502 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,239 per guest
? All-inclusive price from $3,862 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $3,329 per guest
? All-inclusive price from $3,952 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,509 per guest
? All-inclusive price from $4,132 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $3,599 per guest
? All-inclusive price from $4,222 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed easily converted to twins.
? Cruise only from $4,599 per guest
? All-inclusive price from $5,222 per guest
Classic Suite
Classic Suite
Relax in 400 to 530 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $5,599 per guest
? All-inclusive price from $6,222 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $6,399 per guest
? All-inclusive price from $7,022 per guest
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
7-for-7
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
$2,962
$2,339
THIS
SAILING