San Juan & the Virgin Islands

Set sail into the charm of San Juan, where your small ship awaits, moored perfectly in the heart of Old San Juan. From the comfort of your deck, gaze at the magnificent El Morro Fortress, a proud UNESCO World Heritage Site that reflects centuries of history. As you step ashore, the cobblestone streets lined with vibrant colonial buildings invite you to explore and immerse yourself in the city’s rich culture. This is more than a stop; it’s a glimpse into the soul of Puerto Rico.

Cruz Bay, the energetic heart of St. John, welcomes you with its picturesque harbor and relaxed charm. Nestled in the U.S. Virgin Islands, it's an ideal gateway for both adventure and leisure. Stroll through vibrant streets adorned with quaint shops and local restaurants serving authentic flavors. Breathtaking beaches with crystal-clear waters invite moments of calm or adventure, depending on your mood. Whether you’re eager to explore lush hiking trails or immerse yourself in watersports, Cruz Bay delivers an unforgettable experience with a unique island flair.

Nestled amidst vibrant emerald hills, Basseterre charms with its picturesque Georgian architecture and inviting Caribbean allure. Beyond the lively town center, discover the Brimstone Hill Fortress National Park, a UNESCO World Heritage Site that showcases the island’s rich history and exceptional natural beauty.

St. Barts, with its Riviera-inspired beaches and luxurious charm, is the Caribbean's most fashionable escape. Stroll past quaint gingerbread houses, savor a refreshing ti punch by the sea, or browse designer boutiques for unique island finds. The alluring mix of glamour and laid-back island vibes makes it easy to see why this destination captivates so many.

Travelers can’t help but notice the colorful blend of pastel-hued buildings lining Philipsburg’s streets—a warm welcome to this vibrant Caribbean gem. Nestled on the Dutch side of St. Maarten, this port town shines with energy. Its famed Front Street invites visitors to shop for handcrafted treasures, explore jewelry stores, or dine at authentic Creole eateries. And for those feeling adventurous, there are bustling casinos and stylish boutiques to discover. Established back in 1493 during Columbus’ era, Philipsburg combines history with lively island charm.

Jost Van Dyke may be small in size, but it offers some of the most unforgettable experiences. Take a trip to the protected tranquility of Diamond Cay National Park or snorkel through the vibrant coral reefs of Sandy Spit teeming with marine life. Feel adventurous? Captain your own vessel as you navigate the Sir Francis Drake Waterway. End your day with a refreshing drink, feet in the sand, as you marvel at the glowing lights of your Windstar ship in the calm harbor.

Feel the magic of nature as your ship glides over one of the ocean's most mesmerizing coral reefs, the Bank Barrier. Upon arrival, discover Prickly Pear Island, a serene haven boasting unspoiled beaches and vibrant prickly pear cacti. Though uninhabited, this island welcomes visitors with a charming beach bar and opportunities for water adventures. Nearby, the famous site known as “The Baths” invites exploration. Marvel at house-sized boulders that create breathtaking underground pools and secret caverns. Please note: For an even smoother day, guests must book shore excursions through Windstar to access Gun Creek.

Step ashore and be captivated by the historic grandeur of El Morro fortress, a spectacular UNESCO World Heritage Site. From the deck of your elegant ship, take in the charming kaleidoscope of San Juan’s colonial architecture, just steps away from the energetic heart of Old San Juan.