San Juan & the Virgin Islands

Prepare to be transported to centuries past as you stand before the grandeur of El Morro fortress, a UNESCO World Heritage Site that defines San Juan's historic charm. From the deck of your ship, gracefully moored in the heart of Old San Juan, drink in the sight of brightly colored colonial buildings—the perfect frame for this iconic Caribbean escape.

Cruz Bay is the beating heart of St. John, offering visitors a delightful mix of charm and easy-going island life. This waterfront town is where stunning beaches meet vibrant local culture. Whether you’re strolling past cheerful shops, savoring a fresh island-inspired meal, or exploring stories of the past at historic landmarks, Cruz Bay invites you to unwind. From relaxing by crystal-clear waves to discovering the island’s scenic trails, this is the starting point for countless adventures.

Bright Georgian-style buildings backed by lush green hills make Basseterre one of the Caribbean's most charming capitals. Just outside the town, nature and history come together at Brimstone Hill Fortress National Park. This remarkable UNESCO World Heritage Site offers sweeping views and a glimpse into the island’s past.

Step into the charm of St. Barts, where the glitz of the French Riviera meets Caribbean serenity. Stroll past whimsical gingerbread cottages and follow in the footsteps of celebrities who adore this chic getaway. Treat yourself to high-end shopping at elegant, duty-free boutiques or pause for a moment of indulgence with the island's signature ti punch. Along the shoreline, sleek kite surfers glide effortlessly, adding a touch of adventure to the breathtaking vistas.

Step off the ship into Philipsburg, a vibrant town where Dutch charm meets Caribbean spirit. Its pastel-colored streets unfold like a storybook, filled with treasure troves of unique souvenirs and artisan finds. Just a stroll away from the harbor, history whispers along Front Street, now a lively hotspot for dining, shopping, and entertainment. Savor Creole specialties at cozy local eateries, or explore stylish boutiques, glimmering jewelry shops, and exciting casinos. Philipsburg is an island escape that pairs its colorful past with a bustling, modern-day energy certain to captivate.

On this tiny eight-square-mile gem, boundless adventures await. Explore the serene beauty of Diamond Cay’s national park or glide through crystal-clear water as you snorkel beside vibrant sponges and angelfish at Sandy Spit. Feeling adventurous? Navigate your own boat along the legendary Sir Francis Drake Waterway. After a day filled with island discoveries, sip a refreshing cocktail on the sandy shore while gazing at your majestic Windstar ship, illuminated in the tranquil harbor.

The ship glides over the astonishingly clear waters above Bank Barrier Reef, ushering you toward Prickly Pear Island—a paradise brimming with prickly pear cacti. Though uninhabited, this serene spot boasts a charming beach bar and fun water sports activities on its white sandy shores. Nearby, discover the breathtaking geological wonder of The Baths, a fascinating cluster of massive boulders creating natural pools and dramatic caves. Experience the magic of this tropical hideaway, surrounded by raw beauty and unforgettable sights.

Step off your small ship and step back in time at El Morro, one of San Juan's remarkable UNESCO World Heritage Sites. This centuries-old fortress is a testament to the island’s rich history, offering sweeping views of the ocean. From your prime docking point in Old San Juan, the charm of the city’s colorful colonial architecture is just a stroll away, creating a seamless blend of coastal relaxation and cultural exploration.