San Juan & the Virgin Islands

Step ashore and be greeted by the grandeur of El Morro, a historic fortress overlooking the glistening sea and steeped in centuries of rich heritage. From the deck of your thoughtfully designed ship, take in the vibrant colors of San Juan’s colonial architecture, all nestled in the lively heart of Old San Juan. Immerse yourself in the charm of cobblestone streets just steps from your mooring, where history, culture, and inviting local warmth await.

Located on the beautiful island of St. John, Cruz Bay greets you with its relaxed charm and stunning vistas. This delightful harbor town is the gateway to the island’s tranquil beaches, clear waters, and lush hiking trails. Beyond its natural beauty, Cruz Bay boasts an inviting mix of boutique shops, local eateries, and historic landmarks. Whether you’re savoring fresh seafood, strolling along the waterfront, or setting out to explore nearby coves, Cruz Bay offers a welcoming escape where adventure and serenity meet.

St. Barts, the jewel of the Caribbean, combines French elegance with sunlit beauty. Bask on pristine beaches that radiate charm, browse exquisite boutiques, or indulge in the island's signature ti punch while waves dance in the breeze. This glamorous haven, dotted with gingerbread cottages, is a favorite of jet-setters and a perfect retreat for both relaxation and adventure.

Basseterre’s Georgian-style buildings are set against a lush, green hillside, blending history with natural beauty. As you explore the charming streets, you’ll notice how the town holds its place as one of the Caribbean's most picturesque capitals. Just outside the city, discover Brimstone Hill Fortress National Park, a UNESCO World Heritage Site that protects a quarter of St. Kitts with its historical significance and stunning vistas.

Philipsburg welcomes you with pastel-colored buildings and vibrant shopping streets, a true gem on the Dutch side of St. Maarten. Located near the harbor, it’s a delightful blend of colorful history and energetic charm. Front Street, the heart of this lively town, offers everything from Creole restaurants to stylish boutiques and fine jewelry stores. For those feeling lucky, lively casinos add an extra spark to your day. Come and explore this iconic island destination where tradition meets modern-day Caribbean flair.

On just eight square miles of paradise, Jost Van Dyke offers captivating adventures. Explore Diamond Cay’s serene national park, uncover underwater treasures while snorkeling among vibrant reefs near Sandy Spit, or captain your own boat along the iconic Sir Francis Drake Waterway. As the sun sets, retreat to the beach for a refreshing drink, where the sight of your glowing Windstar ship in the tranquil harbor completes a perfect day.

Feel the rhythm of the Caribbean as your ship glides over the sparkling Bank Barrier coral reef. Soon, you’ll arrive at the peaceful haven of Prickly Pear Island, a unique sanctuary dotted with its namesake prickly pear cacti. This uninhabited gem boasts untouched natural beauty, complemented by a small beach bar and water sports facilities. Nearby, discover "The Baths," a stunning collection of enormous granite boulders that create hidden pools and otherworldly caves, inviting exploration and wonder.Please note: Only guests with shore excursions booked through Windstar Cruises can be tendered to Gun Creek.

Step back in time as you approach the majestic El Morro fortress, a proud UNESCO World Heritage Site. From the decks of your ship, moored right in the heart of historic Old San Juan, take in the vibrant charm of the city’s cobblestone streets and eye-catching colonial architecture.