Gems of the Leeward Islands

From $4,099 per person

11 days

Ship: Star Seeker

Gems of the Leeward Islands
Windstar Cruises

With 10 days instead of the usual 7,&nbsp; on this cruise you have time to take in the full measure of this most iconic parts of the Caribbean. Everywhere you look is another cover shot image. Dazzling white sand turns the shallows mesmerizing shades of peacock and mermaid, weathered fortresses point cannons at long-vanished schooners, natural pools warm gently under the mid-day sun. On your private ship, you&rsquo;re equally at home in exclusive harbors and anchored off barefoot beaches, so you can see it all. Snorkel or dive on vibrant coral reefs. Follow your siren inland to rainforest adventures or duty-free boutiques. Thank your lucky&nbsp;<em>Star Pride&nbsp;</em>for bringing you here.<br />
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Journey Summary

  • Day 1 - Mar. 27, 2026, Fri. - San Juan
  • Day 2 - Mar. 28, 2026, Sat. - CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
  • Day 3 - Mar. 29, 2026, Sun. - St. John's
  • Day 4 - Mar. 30, 2026, Mon. - Les Saintes
  • Day 5 - Mar. 31, 2026, Tue. - Pigeon Island
  • Day 6 - Apr. 1, 2026, Wed. - St. George's
  • Day 7 - Apr. 2, 2026, Thu. -
  • Day 8 - Apr. 3, 2026, Fri. - Gustavia
  • Day 9 - Apr. 4, 2026, Sat. - Jost Van Dyke, Great Harbour
  • Day 10 - Apr. 5, 2026, Sun. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 11 - Apr. 6, 2026, Mon. - San Juan

Itinerary Highlights

Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.

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Detailed Itinerary

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

Day 1 - March 27, 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 - March 28, 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&#39;s a popular destination for tourists seeking relaxation, hiking, and water sports. As the island&#39;s main port and hub, Cruz Bay offers a charming blend of local shops, restaurants, and historical sites.

Day 3 - March 29, 2026

St. John's

St. John&rsquo;s is a city of Old World charm and elegance which lingers in the varied architecture of Georgian, Victorian, Vernacular, Romantic and International flavors.&nbsp; The picturesque seafront where tiny, colorful boats are moored, the cheerful wooden buildings carefully refurbished to retain their original features, the vibrant Market Street offering vegetables, fruit and fish and the duty-free Heritage Quay shopping area provide a delightful atmosphere to captivate you.&nbsp; Sites to see include St. John&rsquo;s Cathedral with its white Baroque towers, the Botanical Garden, St. John&rsquo;s Antigua Lighthouse, and Fort James.

Day 4 - March 30, 2026

Les Saintes

This is the Caribbean as you&rsquo;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 5 - March 31, 2026

Pigeon Island

The UNESCO site Pitons&rsquo; 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 6 - April 01, 2026

St. George's

Inhale the intoxicating aroma of the &ldquo;Isle of Spice&rdquo; 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 7 - April 02, 2026

Day 8 - April 03, 2026

Gustavia

Affectionately known as St. Barts, the Caribbean&rsquo;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&rsquo;s signature ti punch as kite surfers fly by.

Day 9 - April 04, 2026

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it&rsquo;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 &nbsp;Drake Waterway. After all that, you&rsquo;ll be ready for an evening drink on the beach &mdash; where you can admire your Windstar ship aglow in the harbor.

Day 10 - April 05, 2026

Virgin Gorda / Prickly Pear, British Virgin Islands

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<li><strong>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 &ldquo;The Baths,&rdquo; which form huge underground pools and caverns.</strong></li>
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<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>

Day 11 - April 06, 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.

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Mar 27, 2026

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