San Juan & the Virgin Islands
 
San Juan to San Juan
Fri Feb 6, 2026 - Fri Feb 13, 2026,
 7 days
 on Star Seeker
?All-inclusive from
$2,999
?Cruise Only From
$2,999
VIEW ALL SAILING
DATES & FARES
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
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
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
Day 2: CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
VIEW THE JOURNEY
Day 3: 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.
VIEW THE JOURNEY
Day 4: 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.
VIEW THE JOURNEY
Day 5: Philipsburg, 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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
Day 7: Virgin Gorda / Prickly Pear, British Virgin Islands
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
VIEW THE JOURNEY
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: 
Fri Feb 6
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sat Feb 7
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 8
Basseterre
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Feb 9
Gustavia
Arrive:  7:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Feb 10
Philipsburg, St. Maarten
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Feb 11
Jost Van Dyke, Great Harbour
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Feb 12
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Feb 13
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 Seeker
A New All-suite Star on the Horizon
LEARN MORE →
Accommodations & Pricing
Oceanview Suite
Oceanview Suite
Experience the perfect blend of style and functionality in this thoughtfully designed 203-square-foot suite. The well-planned layout creates an ideal retreat with plenty of natural light, a view of the sea, a walk-in mosaic glass shower and an inviting queen bed (convertible into two twins if desired), perfect for unwinding after a day of fun and exploration.
? Cruise only from $2,999 per guest
? All-inclusive price from $2,999 per guest
Infinity Suite
Infinity Suite
This 280-square-foot suite features a wide floor-to-ceiling infinity window that allows for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. Your suite features an inviting queen bed (convertible into two twin beds if desired), a walk-in mosaic glass shower and a comfortable living area where you can lounge and enjoy the view.
? Cruise only from $3,299 per guest
? All-inclusive price from $3,299 per guest
Vista Infinity Suite
Vista Infinity Suite
Located on deck 7, this 280-square-foot suite features a wide floor-to-ceiling infinity window that allows for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. Your suite features an inviting queen bed (convertible into two twin beds if desired), a walk-in mosaic glass shower and a comfortable living area where you can lounge and enjoy the view.
? Cruise only from $3,499 per guest
? All-inclusive price from $3,499 per guest
Veranda Suite
Veranda Suite
Stylish comfort and ocean views welcome you to this 225-square-foot suite. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $3,899 per guest
? All-inclusive price from $3,899 per guest
Premier Veranda Suite
Premier Veranda Suite
 Located at the middle of the ship, these 225-square-foot suites welcome you with stylish comfort and beautiful ocean views. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $4,249 per guest
? All-inclusive price from $4,249 per guest
Triple Premier Veranda Suite
Triple Premier Veranda Suite
Located on deck 6, this 246-square-foot suite welcomes you with stylish comfort and stunning ocean views. Featuring an inviting queen bed (convertible into two twin beds if desired) and a pull-out sofa in the living area, the suite allows for triple occupancy. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $4,299 per guest
? All-inclusive price from $4,299 per guest
Triple Infinity Suite
Triple Infinity Suite
This roomy 301-square-foot suite features a wide floor-to-ceiling infinity window in the bedroom, allowing for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. This suite also features an inviting queen bed (convertible into two twin beds if desired) and a pull-out sofa in the separate living area, allowing for triple occupancy. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $4,299 per guest
? All-inclusive price from $4,299 per guest
Vista Veranda Suite
Vista Veranda Suite
Located on deck 7, this 268-square-foot suite welcomes you with stylish comfort and stunning ocean views. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $4,499 per guest
? All-inclusive price from $4,499 per guest
Deluxe Suite
Deluxe Suite
This 288-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed (convertible into two twin beds if desired) and its own sliding glass door with balcony access, while the bathroom includes a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $5,599 per guest
? All-inclusive price from $5,599 per guest
Classic Suite
Classic Suite
Step into a stylish and bright open living area with a spacious adjacent bedroom. This 353-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed that can be converted into two twins if desired, while the bathroom includes a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $6,499 per guest
? All-inclusive price from $6,499 per guest
Star Suite
Star Suite
Step into a stylish and bright open living area with a spacious adjacent bedroom. This 380-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed (convertible into two twin beds if desired) and its own sliding glass door with balcony access, while the bathroom includes a bathtub and walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $6,899 per guest
? All-inclusive price from $6,899 per guest
Horizon Owner’s Suite
Horizon Owner’s Suite
This luxurious 548-square-foot suite combines floor-to-ceiling windows and a wrap-around balcony for an unparalleled cruising experience. Perfect for evening cocktails or a private dinner, the wrap-around balcony adds 248 square feet of space and offers unobstructed views of the sea. The suite boasts a separate entryway — as well as separate dining and living areas — and a guest powder room. The bedroom includes an inviting king bed (convertible into two XL twin beds if desired), and the bathroom features a luxurious double walk-in mosaic glass shower with rain head and body jets. For family bookings, the adjacent suite can be combined to provide extra bedrooms and space for entertaining.
? 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
7-for-7
Early Booking Offer 2026
Last Minute Cruise Deals
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, Nov 3 - Sat, Nov 9, 2024
STAR PRIDE
$2,782
$2,248
Sat, Nov 16 - Sat, Nov 23, 2024
STAR PRIDE
$3,096
$2,473
Sat, Nov 30 - Sat, Dec 7, 2024
STAR PRIDE
$3,141
$2,518
Sun, Oct 26 - Sun, Nov 2, 2025
STAR PRIDE
$3,222
$2,599
Sun, Nov 2 - Sun, Nov 9, 2025
STAR PRIDE
$3,422
$2,799
Sun, Nov 9 - Sun, Nov 16, 2025
STAR PRIDE
$3,222
$2,599
Sun, Nov 16 - Sun, Nov 23, 2025
STAR PRIDE
$3,222
$2,599
Sun, Nov 23 - Sun, Nov 30, 2025
STAR PRIDE
$3,222
$2,599
Sun, Nov 30 - Sun, Dec 7, 2025
STAR PRIDE
$3,222
$2,599
Fri, Jan 23 - Fri, Jan 30, 2026
STAR SEEKER
$3,199
$3,199
Fri, Feb 6 - Fri, Feb 13, 2026
STAR SEEKER
$2,999
$2,999
THIS
SAILING
Fri, Feb 20 - Fri, Feb 27, 2026
STAR SEEKER
$3,099
$3,099
Fri, Mar 6 - Fri, Mar 13, 2026
STAR SEEKER
$2,999
$2,999