San Juan & the Virgin Islands
 
San Juan to San Juan
Sun Nov 9, 2025 - Sun Nov 16, 2025,
 7 days
 on Star Pride
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Starting from $2,599 USD
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San Juan to San Juan
Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant ship is already there.
voyage map
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Day 1: 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.
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Day 3: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 4: Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
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Day 5: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 6: Les Saintes
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
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Day 7: Marigot, St. Martin
Established around 1689, Marigot is the attractive capital of French St. Martin, with its brightly colored houses, a lively open-air market, secluded beaches, and pretty waterfront promenade. Because of its tax-free status, Marigot is a popular center for duty-free shopping, where all of the world’s most prestigious brands can be found.  Originally the area was marshy, and surrounded by mangroves. In the 1970s part of the bay was filled in to extend Marigot into a larger city with a marina. Overlooking Marigot is Fort St. Louis, the largest historical monument in St. Martin with an impressive panoramic view of the bay.
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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
El Morro
Admire the incredible views from El Morro’s 16th century ramparts, a UNESCO World Heritage Site, in San Juan.
El Yunque
Go for a hike in Puerto Rico’s El Yunque National Rainforest.
Jost Van Dyke
 Let the Bubbly Pool on Jost Van Dyke wash your cares away.
Pirate Grog
Learn all about the pirates’ favorite grog.
St. Barts
 Mingle with the glitterati in St. Barts.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sun Nov 9
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Mon Nov 10
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Nov 11
St. George's
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Nov 12
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Nov 13
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Nov 14
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Nov 15
Marigot, St. Martin
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Sun Nov 16
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
“This cruise has it all. History and culture in San Juan, shopping and sightseeing in St. Maarten and St. Thomas, and relaxation on world-class beaches on Virgin Gorda and Jost Van Dyke.”
The Story
There’s a reason the rich and famous head to the British Virgin Islands when they want peace and privacy. These islands combine European sophistication with a casual laid-back attitude, plus some of the most stunning beaches in the Caribbean. Activities here prioritize recreation and relaxation over commercial amusements, and the islands are less developed than many – making this one of the world’s favorite yachting destinations and a perfect place to explore on one of Windstar’s unique small ships.
 
These craggy volcanic islands may be a bit sleepy, but with their lush rainforests, crescent beaches, and turquoise water, there are plenty of opportunities for adventure. Kayaking, sailing, wilderness hiking, and snorkeling are just a few of the ways to explore these bays and harbors, and you never know when you’ll encounter something unexpected. Even the largest of these islands has only 20,000 residents, so you can still find hidden beaches, protected coves, and secluded beach bars that are often accessible only by boat. And with Windstar’s Watersports Platform, you can enjoy this watery wonderland without ever going ashore.
 
Insider Tips:
• The Baths on Virgin Gorda are a must. Giant granite boulders form a series of plunge pools and hidden grottoes on the beach – one of the most scenic spots in the Caribbean.

• Since a volcano destroyed its capital in 1995, Montserrat has been mostly off the tourist radar. But not for lack of attractions. Rainforest still covers much of the island, and the abandoned buildings buried in ash are like visiting a modern Pompeii.

• Beach bars are synonymous with the Caribbean, but none are quite like those on Jost Van Dyke. If you visit the Soggy Dollar Bar you must try a Painkiller – a unique rum drink that also comes in a virgin version.

• St. Thomas is known as the best shopping spot in the Caribbean, and one of the top ten shopping areas in the world. Shop for duty-free bargains in Charlotte Amalie where you’ll find everything from custom leather sandals to authentic shipwreck coins.

• If you’re into photography, take your camera for a walk through Old San Juan. The colorful buildings are pure eye candy, and notice the doors. Barred, brassed, arched or painted, they hint at Puerto Rico’s diverse cultural influences.
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 $2,599 per guest
? All-inclusive price from $3,292 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 $2,699 per guest
? All-inclusive price from $3,392 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 $2,799 per guest
? All-inclusive price from $3,492 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 $2,959 per guest
? All-inclusive price from $3,652 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 $3,039 per guest
? All-inclusive price from $3,732 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 $3,199 per guest
? All-inclusive price from $3,892 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 $3,859 per guest
? All-inclusive price from $4,552 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 $4,592 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 $4,792 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 $4,892 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 $5,099 per guest
? All-inclusive price from $5,792 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 $5,999 per guest
? All-inclusive price from $6,692 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 $7,099 per guest
? All-inclusive price from $7,792 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
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Nov 30 - Sat, Dec 7, 2024
STAR PRIDE
$3,842
$3,149
Sun, Oct 26 - Sun, Nov 2, 2025
STAR PRIDE
$3,292
$2,599
Sun, Nov 2 - Sun, Nov 9, 2025
STAR PRIDE
$3,492
$2,799
Sun, Nov 9 - Sun, Nov 16, 2025
STAR PRIDE
$3,292
$2,599
THIS
SAILING
Sun, Nov 16 - Sun, Nov 23, 2025
STAR PRIDE
$3,292
$2,599
Sun, Nov 23 - Sun, Nov 30, 2025
STAR PRIDE
$3,292
$2,599
Sun, Nov 30 - Sun, Dec 7, 2025
STAR PRIDE
$3,292
$2,599
Fri, Jan 23 - Fri, Jan 30, 2026
STAR SEEKER
$3,992
$3,299
Fri, Feb 6 - Fri, Feb 13, 2026
STAR SEEKER
$3,692
$2,999
Fri, Feb 20 - Fri, Feb 27, 2026
STAR SEEKER
$3,792
$3,099
Fri, Mar 6 - Fri, Mar 13, 2026
STAR SEEKER
$4,992
$4,299