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San Juan & the Virgin Islands
Nov 29, 2026 — Dec 6, 2026
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Beyond Inclusive Package
SAN JUAN → SAN JUAN
7 Nights on Star Pride
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 like St. Thomas in favor of less-visited destinations like Montserrat. Bypass the major cruise terminals in favor of marinas and anchorages exclusive to small yachts on this Caribbean cruise. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.





Popular Highlights
In San Juan, admire the incredible views from El Morro’s 16th-century ramparts, a UNESCO World Heritage Site.
Go for a hike in Puerto Rico’s El Yunque National Rainforest.
Shop Gustavia's duty-free boutiques or grab a glass of the island’s signature ti' punch at a beachside bar.
Mingle with the glitterati in St. Barts.
Take a stroll in the St. John’s National Park, which covers over half of the islands.
Let the Bubbly Pool on Jost Van Dyke wash your cares away.
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Insider Tips

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.
San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Windstar Hotel
San Juan: Old San Juan Natl Historic Parks Walking Tour with Transfer to Airport
San Juan, Bacardi Rum Tour & Tasting- With Transfer to Windstar Hotel
San Juan, Concierge Collection: Half Day Private SUV with Guide
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
St. John, Champagne Catamaran Sail
St. John, Champagne Catamaran Sail
St. John, Lind Point Trail Eco Hike
St. John, Trunk Bay Snorkeling Experience
St. John, Island tour Featuring Annaberg Ruins

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.
Gustavia, Concierge Collection: Jet Ski
Gustavia, Concierge Collection: Savor St Barts
St. Barts, Concierge Collection: Sunset Cruise
St. Barts: Intimate Island Tour
St Barts, Concierge Collection: St. Barthelemy Beach Day
Gustavia, Concierge Collection: Scuba Dive 2 Tank
St. Barts: Sailing Catamaran Adventure
Gustavia, Concierge Collection: Scuba Dive 1 Tank
St. Barts: Independent Explorer by Car

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.
Basseterre: Caribbean Scenic Railway
Basseterre, Concierge Collection: Caribbean Cooking, History & Folklore in St. Kitts
Basseterre: Sky Safari Zipline Adventure
Basseterre, Nevis Panoramic and Beach Tour
Basseterre: Snorkel Safari
Basseterre, Brimstone Hill Fortress & Fairview Great House
Basseterre: St Kitts Quad ATV Adventure
Basseterre, Island History & Rum Tasting

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.
Philipsburg, Savor St. Maarten Foodie Tour
St. Maarten, Concierge Collection: Half Day Private Island Tour in SUV or Deluxe Mini Van
St. Maarten: Under Two Flags Island Tour
St. Maarten: Americas Cup Sailboat Racing

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.
Jost Van Dyke, Catamaran Cruise & Swim to Norman Island

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
Virgin Gorda: Highlights & Bath Tour
Virgin Gorda: Snorkel Adventure
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