San Juan & the Virgin Islands
 
7 DAYS
Star Pride
San Juan to San Juan
Departure Date:
Price from $2,299 USD per guest
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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 2: St. Thomas
St. Thomas has something for everyone who loves the outdoors.  Magen’s Bay, the island’s most popular beach with its heart-shaped protected bay, the incomparable view of the Caribbean found climbing the famous 99 steps of Charlotte Amalie, world-famous Mahogany Run Golf Course, the Skyride that soars 700 feet above the city, and snorkeling and sailing, Sightsee the St. Thomas Synagogue, built in 1833, Fort Christian, built in 1680, Blackbeard’s Castle, a 1679 watchtower, and the childhood home of French Impressionist Camille Pissarro, now an art gallery.
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Day 3: 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 4: Little Bay
Today we visit “Pompeii of the Caribbean”—an island that is half lush and green, half gray and covered in ash by a volcano in 1995. And if a half-buried city isn’t intriguing enough, there are black-sand beaches and a perplexing Irish heritage to explore.
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Day 5: St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
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Day 6: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
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Day 7: Virgin Gorda
A beautiful coral reef wavers just beneath you as your ship makes the break into the heart of Spanish Town, the Yacht Harbor Marina,Located to the south of Spanish Town lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.
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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.
Montserrat
Discover a town swallowed by a volcano during a rare visit to Montserrat.
Pirate Grog
Learn all about the pirates’ favorite grog.
St. Barts
 Mingle with the glitterati in St. Barts.
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“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.
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.
Cooking Demonstrations
Open Bridge
Friendly and Relaxed Atmosphere
Local and Live Performances
Signature Sail Away
Crew Talent Show
Enjoy regionally inspired treatments at World Spa by Windstar
Take In The Sun
Complimentary 24 Hour Room Service
Relax at the Pool or Hot Tub
Relax With A Morning Yoga Session
Genuine and Thoughtful Crew
Signature Onboard Barbecue
Shopping With The Chef
Watersports Platform
Accommodations & Pricing
This all-suite ship will complete 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.
$2,299 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, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
$2,399 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.
$2,499 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.
$2,599 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.
$2,699 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.
$2,899 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.
$3,299 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.
$3,399 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.
$3,599 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.
$3,699 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.
$4,299 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.
$5,099 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, two flat-screen TVs and DVD players, and a full master bath and separate powder room indulge you in spacious comfort. 
$6,099 per guest
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
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Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
Call For Availability
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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