San Juan & the Virgin Islands
 
San Juan to San Juan
Sun Dec 27, 2026 - Sun Jan 3, 2027,
 7 days
 on Star Pride
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Starting from $2,699 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
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sun Dec 27
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Mon Dec 28
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Dec 29
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Dec 30
Basseterre
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Dec 31
Philipsburg, St. Maarten
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Jan 1
Jost Van Dyke, Great Harbour
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Jan 2
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Jan 3
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.
Accommodations & Pricing
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 $2,699 per guest
? All-inclusive price from $2,699 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
ALL DATES &
FARES
Early Booking Offer 2026 & 2027
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
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
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
$4,192
$3,499
Fri, Feb 6 - Fri, Feb 13, 2026
STAR SEEKER
$4,692
$3,999
Fri, Feb 20 - Fri, Feb 27, 2026
STAR SEEKER
$3,992
$3,299
Fri, Mar 6 - Fri, Mar 13, 2026
STAR SEEKER
$5,092
$4,399
Sun, Nov 15 - Sun, Nov 22, 2026
STAR PRIDE
$2,499
$2,499
Sun, Nov 29 - Sun, Dec 6, 2026
STAR PRIDE
$2,499
$2,499
Sun, Dec 13 - Sun, Dec 20, 2026
STAR PRIDE
$2,499
$2,499
Sun, Dec 27 - Sun, Jan 3, 2027
STAR PRIDE
$2,699
$2,699
THIS
SAILING
Sun, Jan 10 - Sun, Jan 17, 2027
STAR PRIDE
$2,499
$2,499