Masterpieces at Sea: Gems of the Leeward Islands

From $3,657 per person

12 days

Ship: Star Pride

Masterpieces at Sea: Gems of the Leeward Islands

Journey Summary

  • Day 1 - Oct. 28, 2026, Wed. - San Juan
  • Day 2 - Oct. 29, 2026, Thu. - CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
  • Day 3 - Oct. 30, 2026, Fri. - Gustavia
  • Day 4 - Oct. 31, 2026, Sat. - Basseterre
  • Day 5 - Nov. 1, 2026, Sun. - Falmouth Harbour
  • Day 6 - Nov. 2, 2026, Mon. - Les Saintes
  • Day 7 - Nov. 3, 2026, Tue. - Pigeon Island
  • Day 8 - Nov. 4, 2026, Wed. - St. George's
  • Day 9 - Nov. 5, 2026, Thu. -
  • Day 10 - Nov. 6, 2026, Fri. - Jost Van Dyke, Great Harbour
  • Day 11 - Nov. 7, 2026, Sat. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 12 - Nov. 8, 2026, Sun. - San Juan

Detailed Itinerary

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

Day 1 - October 28, 2026

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 - October 29, 2026

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 - October 30, 2026

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 - October 31, 2026

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 - November 01, 2026

Falmouth Harbour

It’s said that Antigua has 365 beaches – one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Day 6 - November 02, 2026

Les Saintes

This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Day 7 - November 03, 2026

Pigeon Island

The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.

Day 8 - November 04, 2026

St. George's

Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

Day 9 - November 05, 2026

Day 10 - November 06, 2026

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 11 - November 07, 2026

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 12 - November 08, 2026

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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