Boston Sights, Warm Caribbean Nights
 
Boston to San Juan
Wed Oct 23, 2024 - Sun Nov 3, 2024,
 11 days
 on Star Pride
?All-inclusive from
$3,778
?Cruise Only From
$2,799
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Boston to San Juan
Venture from cosmopolitan Boston to warm Bermuda beaches and the picturesque Caribbean shorelines during this 11-day cruise. Kayak amid gliding sea turtles and radiant tropical fish, explore pastel-hued Bermuda shops, and dine on traditional codfish dishes, spiny lobster and seared tuna steaks during an overnight stay in Hamilton. Tour the forts and historic sites St. George’s, a designated UNESCO World Heritage Site, or relax on one of their beautiful ucroweded beaches during your overnight port stay. Shop for one-of-a-kind jewelry or distinctly classic island casual wear at St. Bart boutiques in Gustavia.
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: Basseterre
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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Day 11: Virgin Gorda / Prickly Pear
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. Althought 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
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Day 12: 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
Hamilton
Overnight in Hamilton with plenty of time for snorkeling amid the abundance of marine life.
Spa
Spend relaxing days at sea with time for making new friends, visiting the spa and attending onboard informational lectures.
St. Barts
Shop the duty-free boutiques of St. Barts.
St. Georges
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
Watersports
PlatformWatersports Platform: 
Wed Oct 23
Boston
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Thu Oct 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Oct 25
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sat Oct 26
Hamilton
Arrive:  8:45 AM
Depart:  
Watersports Platform: 
Sun Oct 27
Hamilton
Arrive:  
Depart:  7:00 AM
Watersports Platform: 
Sun Oct 27
St. George's
Arrive:  10:00 AM
Depart:  
Watersports Platform: 
Mon Oct 28
St. George's
Arrive:  
Depart:  7:00 AM
Watersports Platform: 
Tue Oct 29
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Oct 30
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Oct 31
Gustavia
Arrive:  8:00 AM
Depart:  11:00 PM
Watersports Platform: 
Fri Nov 1
Basseterre
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Nov 2
Virgin Gorda / Prickly Pear
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Nov 3
San Juan
Arrive:  7:00 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 $2,799 per guest
? All-inclusive price from $3,778 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 $2,899 per guest
? All-inclusive price from $3,878 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 $2,999 per guest
? All-inclusive price from $3,978 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 $3,099 per guest
? All-inclusive price from $4,078 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 $3,199 per guest
? All-inclusive price from $4,178 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 $3,399 per guest
? All-inclusive price from $4,378 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 $3,799 per guest
? All-inclusive price from $4,778 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 $3,899 per guest
? All-inclusive price from $4,878 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 $4,099 per guest
? All-inclusive price from $5,078 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 $4,199 per guest
? All-inclusive price from $5,178 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 $6,599 per guest
? All-inclusive price from $7,578 per guest
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
? Call for Availability
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.
? Call for Availability
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.
? Call for Availability
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
DISCOVER WINDSTAR’S DEGREES OF DIFFERENCE
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
Wed, Oct 23 - Sun, Nov 3, 2024
STAR PRIDE
$3,778
$2,799
THIS
SAILING