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INTERNATIONAL NUMBERS HEALTH & SAFETY YACHT CLUB WISHLIST MY WINDSTAR
Call Your Travel Advisor or800.258.7245

San Juan & the Virgin Islands

 
San Juan to San Juan
Mon Dec 20, 2027 - Mon Dec 27, 2027,
 7 days
 on Star Legend
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Starting from $3,199 USD
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OVERVIEW & ITINERARY
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ITINERARY AND SHORE EXCURSIONS

The best on land brought to you by the best at sea. Get to the heart of local cultures with Windstar shore excursions. You don't want to just dip a toe in local culture, you want to dive into the deep end, and that's exactly what Windstar shore excursions are designed to do. All of our excursion are created to provide authentic local experience - the kind travelers like you are looking for. And with more than 2,500 excursions to choose from, you can experience your destination in whatever way is most meaningful to you. Whether you're an outdoor enthusiast, a foodie, a history buff, or someone who loves to get to know the faces behind the many places we travel.

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Date
Port
Arrive
Depart
Marina
Shore
Excursions
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Mon Dec 20
San Juan
Arrive:
Depart:7:00 PM
Watersports Platform: 
+_
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.
Tue Dec 21
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:8:00 AM
Depart:6:00 PM
Watersports Platform: 
4 Available
+_
Cruz Bay is a vibrant waterfront town located on St. John, one of the U.S. Virgin Islands. Known for its stunning beaches, crystal-clear waters, and laid-back atmosphere, it's a popular destination for tourists seeking relaxation, hiking, and water sports. As the island's main port and hub, Cruz Bay offers a charming blend of local shops, restaurants, and historical sites.
4 Shore Excursions Available
+
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St. John, Champagne Catamaran SailBeach | Outdoors
Duration3.5 Hours
Activity LevelEasy-Moderate
$139
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St. John, Champagne Catamaran SailBoating | Outdoors
Duration3 Hours
Activity LevelStrenuous
$149
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St. John, Lind Point Trail Eco HikeHiking | Outdoors
Duration3 Hours
Activity LevelEasy-Moderate
$129
VIEW DETAILS
St. John, Trunk Bay Snorkeling ExperienceOutdoors | Snorkeling
Duration3 Hours
Activity LevelEasy-Moderate
$149
VIEW DETAILS
Wed Dec 22
Basseterre
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
+_
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.
Thu Dec 23
Gustavia
Arrive:7:00 AM
Depart:10:00 PM
Watersports Platform: 
+_
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.
Fri Dec 24
Philipsburg, St. Maarten
Arrive:8:00 AM
Depart:10:00 PM
Watersports Platform: 
+_
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.
Sat Dec 25
Jost Van Dyke, Great Harbour
Arrive:9:00 AM
Depart:10:00 PM
Watersports Platform: 
+_
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.
Sun Dec 26
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:8:00 AM
Depart:5:00 PM
Watersports Platform: 
+_
  • 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. Although 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.
 
Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.
Mon Dec 27
San Juan
Arrive:7:00 AM
Depart:
Watersports Platform: 
+_
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.