San Juan & the Virgin Islands

The majestic El Morro Fortress stands as a proud testament to San Juan's rich history. Pause to take in its commanding presence as your elegant small ship docks right in the heart of Old San Juan. From there, it's easy to marvel at the charming colonial streets that unfold in a tapestry of vibrant colors, each corner steeped in stories of the past. It's a graceful blend of history and modern comfort, with the exclusivity that only small-ship travel offers.

Step ashore into Cruz Bay, the lively heart of St. John in the U.S. Virgin Islands. This picturesque harbor town invites you to explore its charm, from colorful local shops to delightful island dining. Wander through its streets and you’ll uncover a relaxed vibe sprinkled with a touch of history. Known for its turquoise waters and world-class beaches, Cruz Bay is the perfect gateway to outdoor adventures—whether it’s a serene sail, a hike amidst lush greenery, or simply soaking up the tropical sunshine.

Known for its effortless charm, St. Barts blends elegant French flair with the relaxed ambiance of the Caribbean. Explore its golden, Riviera-like beaches or stroll among the inviting gingerbread cottages. Perhaps you’ll catch a glimpse of a celebrity or discover a chic designer boutique. When it’s time to unwind, savor a refreshing ti punch or simply watch kite surfers paint the sky with their graceful moves.

Set against a breathtaking backdrop of emerald-green hills, the charming town of Basseterre radiates warmth and beauty. This Caribbean gem, with its Georgian architecture, exudes a timeless elegance. Venture beyond the town to discover one of the island's treasures: Brimstone Hill Fortress National Park, an awe-inspiring UNESCO World Heritage Site that preserves both history and spectacular vistas.

Step into Philipsburg, a vibrant coastal gem welcoming you with its pastel-colored buildings and lively streets. Nestled on the Dutch side of St. Maarten, this busy harbor town invites you to explore its rich history, starting with Christopher Columbus’s discovery in 1493. Wander along celebrated Front Street where local Creole eateries serve up island flavors, and boutiques tempt you with fine jewelry, chic fashion, and handcrafted treasures. Wrap up your day trying your luck at one of the bustling casinos, capturing the energetic spirit of this unforgettable destination.

Jost Van Dyke may be small at just eight square miles, but it brims with charm and adventure. Explore the nearby national park on Diamond Cay, where nature surrounds you in its quiet beauty. Dive into the crystal-clear waters of Sandy Spit to snorkel among vibrant sea sponges and graceful angelfish. For maritime explorers, there’s the thrill of piloting your own boat through the Sir Francis Drake Waterway. After an adventure-filled day, unwind with a refreshing cocktail on the beach as you watch your stunning Windstar ship glowing softly in the harbor.

Feel the allure of untouched paradise as you sail towards Prickly Pear Island. This small gem, draped with prickly pear cacti, welcomes adventurers with sparkling waters, a cozy beach bar, and lively water activities. Nearby, witness the iconic Baths, where nature has crafted massive granite boulders into magical caves and glistening pools—perfect for exploration. A true escape into the heart of the British Virgin Islands.

Explore the remarkable El Morro fortress, a UNESCO World Heritage site that stands proudly as a symbol of San Juan's rich history. From the comfort of your ship, docked right in the vibrant heart of Old San Juan, admire the vivid colors of colonial architecture, each building telling its own story. It’s an intimate moment to soak up the charm of this enchanting city.