Windstar Cruise

7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]

7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]
Starting from $2,999*

San Juan to San Juan

Ship: Star Pride | Star Seeker

Departure Date : Jan 30 2026 | Feb 13 2026 | Feb 27 2026 | Mar 13 2026

Itinerary

Day San Juan, Puerto Rico
Depart 07:00 PM
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spain’s New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the city’s founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Rico’s best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardo’s bioluminescent bay. "
San Juan, Puerto Rico
Day At Sea

Day St. George's, Grenada
Arrive 09:00 AM Depart 10:00 PM
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.
St. George's, Grenada
Day Bequia, St. Vincent & the Grenadines
Arrive 08:00 AM Depart 10:00 PM
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
Bequia, St. Vincent & the Grenadines
Day Pigeon Island, St. Lucia
Arrive 08:00 AM Depart 05:00 PM
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.
Pigeon Island, St. Lucia
Day Les Saintes, Guadeloupe
Arrive 08:00 AM Depart 05:00 PM
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.
Les Saintes, Guadeloupe
Day Philipsburg, Sint Maarten
Arrive 08:00 AM Depart 02:00 PM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
Day San Juan, Puerto Rico
Arrive 07:00 AM
"Back in the 1500s, Puerto Rico was one of the first Caribbean islands to be settled, and its capital, today's San Juan, became a vital hub of Spain’s New World colonies. The historic part of the city, known as Old San Juan, is now a UNESCO World Heritage Site; it's also a National Historic Site within the U.S. National Park Service. Strolling the narrow cobblestoned streets of Old San Juan, you'll discover a historic treasure surrounded by massive city walls. You can climb the ramparts of imposing fortresses like El Morro, at the entrance to the bay, and visit the Cathedral of San Juan Bautista, one of the oldest churches in the Americas and the final resting place of the city’s founder, Ponce de León. Modern San Juan extends well beyond the historic district and offers diversions of its own. Condado, a lively beachfront neighborhood, has high-rise resorts and trendy waterfront bars. Visitors may sample one of Puerto Rico’s best-known products at Casa Bacardí, the rum distillery across the bay. And stunning natural wonders await just outside the city, including the rain forest and waterfalls of El Yunque National Forest and the otherworldly lights of Fajardo’s bioluminescent bay. "
San Juan, Puerto Rico
 
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