San Juan & the Virgin Islands

From $2,091 per person

8 days

Ships: Star Pride, Star Seeker

San Juan & the Virgin Islands

Journey Summary

  • Day 1 - San Juan
  • Day 2 - CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
  • Day 3 - Basseterre
  • Day 4 - Gustavia
  • Day 5 - Philipsburg, St. Maarten
  • Day 6 - Jost Van Dyke, Great Harbour
  • Day 7 - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 8 - San Juan

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

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.

Day 2

CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)

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.

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.

Day 4

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.

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.

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.

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. 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.

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.

Dates and Prices

(per person*)

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* Per double occupancy. Some pricing may reflect single traveler rate.

Ship

Your cruise ship

The Star Pride ship sails serenely on calm waters under a clear blue sky, showcasing its elegant design.
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About this ship

Star Pride

Star Pride is an elegant, all-suite yacht that delivers Windstar Cruises’ signature small-ship experience with sophistication and style. Designed for just 312 guests, the ship offers a refined alternative to larger cruise vessels—combining personalized service, expansive accommodations, and a relaxed onboard ambiance with the ability to explore some of the world’s most captivating and hard-to-reach destinations.

As part of Windstar’s $250 million Star Plus Initiative, Star Pride underwent a transformative renovation in 2021. The ship was lengthened by 84 feet, resulting in expanded public areas, new culinary venues, and additional suites. Upgrades also included new eco-friendly engines and enhanced environmental systems, positioning the vessel at the forefront of sustainable luxury travel. Though refreshed and modernized, Star Pride retains the intimate, yachting spirit that defines the Windstar experience.

All 156 suites on board are ocean-facing, offering spacious layouts ranging from 277 to over 800 square feet. Designed with a blend of contemporary elegance and classic comfort, each suite features plush bedding, walk-in closets, marble-accented bathrooms with dual vanities, and thoughtful amenities such as Illy espresso machines and L’Occitane bath products. Many suites include private verandas or French balconies, creating a seamless connection to the sea and surrounding landscapes.

Dining on Star Pride is elevated, globally inspired, and entirely complimentary. Amphora, the ship’s main dining room, offers ever-changing menus rooted in fresh, seasonal ingredients. Candles transforms the deck into a romantic open-air steakhouse by night, while Cuadro 44 by chef Anthony Sasso offers bold, modern Spanish cuisine in an intimate, tapas-style setting. Star Grill by Steven Raichlen serves barbecue with international flair in a casual al fresco setting, and the Yacht Club Café is a favorite for fresh pastries, coffee, and light bites throughout the day. In-suite dining is available 24 hours a day for added flexibility.

The ship’s amenities cater to both active travelers and those seeking rest and rejuvenation. A full-service spa and wellness complex offers a variety of treatments, a thermal suite, and a well-equipped fitness center. Open decks and lounges provide ample space for relaxation, while the watersports platform at the stern gives guests direct access to complimentary activities such as kayaking, paddleboarding, and snorkeling when conditions allow.

Thanks to its size and shallow draft, Star Pride is able to navigate narrow waterways and dock in smaller ports that are inaccessible to larger ships. Whether cruising the Norwegian fjords, the coastal towns of the Mediterranean, or the islands of Southeast Asia, the ship brings guests closer to the cultural and natural heart of each destination.

Deckplans

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