San Juan & the Virgin Islands

Feel the magic of Old San Juan as you take in the rich history and charm of El Morro’s iconic silhouette. This impressive fort, a UNESCO World Heritage marvel, stands proudly above the coastline, telling stories of the past. Your ship awaits nearby, nestled within the vibrant heart of San Juan, offering a front-row seat to the cobblestone streets and colorful facades of this enchanting Colonial-era treasure.

Nestled along the turquoise waters of St. John, Cruz Bay is the vibrant heartbeat of the island. This lively hub welcomes travelers with its colorful charm, blending pristine beaches, inviting hiking trails, and endless opportunities for water adventures. Wander through a delightful mix of cozy shops, locally-inspired restaurants, and historical treasures, all set against a laid-back island vibe. Whether you're here to take in the natural beauty or soak in the culture, Cruz Bay is your ideal gateway to discover the best of this pristine paradise.

Step into the charm of Basseterre, where the elegance of Georgian architecture meets a vibrant green backdrop of lush hills. This quaint Caribbean capital brims with character, offering a picturesque blend of history and natural beauty. Venture beyond the town to discover Brimstone Hill Fortress National Park, a UNESCO World Heritage Site, where history and stunning island views combine for an unforgettable experience.

Welcome to St. Barts, the jewel of the Caribbean where European charm meets tropical elegance. Here, white sandy beaches and crystal-clear waters create a picture-perfect retreat. Wander streets lined with gingerbread-style cottages, and you may even spot a celebrity! Browse chic designer boutiques or relax with a refreshing ti punch, the island’s signature cocktail. For a touch of adventure, watch the colorful kite surfers as they glide effortlessly across the surf. St. Barts offers sophistication and natural beauty in perfect harmony.

Discover the vibrant charm of Philipsburg, nestled on St. Maarten’s bustling Dutch side. This lively harbor town greets visitors with a splash of pastel-colored buildings filled with unique shops. Don’t miss exploring Front Street—home to inviting Creole restaurants, elegant jewelry stores, chic boutiques, and lively casinos. Whether you’re seeking relaxation or excitement, Philipsburg offers the perfect blend of Caribbean culture and modern-day thrills.

For such a small island, Jost Van Dyke offers an abundance of unforgettable adventures. Discover the beauty of nearby Diamond Cay's protected national park. Dive into the underwater wonders of Sandy Spit, where brilliant sponges and graceful angelfish dance beneath the waves. Feeling adventurous? Captain your own boat through the famous Sir Francis Drake Waterway. After an exhilarating day, unwind on the beach with a refreshing drink. Let your gaze wander to the harbor, where your elegant Windstar ship glows softly in the evening light, awaiting your return.

As your ship gently glides past the sparkling waters of the Bank Barrier coral reef, you'll approach the tranquil haven of Prickly Pear Island. Its rugged charm is highlighted by scattered prickly pear cacti, giving the island its name. Despite being uninhabited, this serene spot offers a welcoming beach bar and thrilling water sports activities. Nearby, discover the incredible natural wonder of "The Baths," where giant boulders create secluded pools and breathtaking underground caverns—an unforgettable chance to connect with nature's raw beauty.

Step back in time as your ship docks in the heart of Old San Juan. From your luxurious vantage point, admire the colorful colonial architecture that’s filled with history and charm. And don’t miss the iconic El Morro fortress, standing proudly as one of the city’s UNESCO World Heritage gems.