San Juan & the Virgin Islands

San Juan is a treasure trove of history and vibrant charm. El Morro, a centuries-old fortress and a UNESCO World Heritage Site, stands proudly overlooking the harbor. From the comfort of your luxurious small ship, conveniently docked in the heart of Old San Juan, you’ll be treated to views of brightly colored colonial buildings and lively streets. This is a destination where history and modern culture blend seamlessly, creating an unforgettable experience.

Welcome to Cruz Bay, the beating heart of St. John and a gateway to Caribbean charm. This picturesque town feels like a postcard come to life, with turquoise waters lapping at its shores and a vibrant yet unhurried vibe. Start your day exploring its lively streets dotted with eclectic shops and restaurants serving fresh island flavors. Whether you're soaking up the sun on a pristine beach, hiking scenic trails, or discovering its rich history, Cruz Bay effortlessly captures the essence of island relaxation and adventure.

Discover the charm of Basseterre, one of the Caribbean’s most picturesque small capitals. With its beautiful Georgian architecture surrounded by lush green hills, this quaint town invites exploration. Venture beyond the city and uncover the wonders of St. Kitts, where over a quarter of the island is protected as Brimstone Hill Fortress National Park. This UNESCO World Heritage Site promises breathtaking views and a deep dive into history.

St. Barts, the Caribbean’s stylish gem, offers an irresistible mix of French charm and island allure. Stroll among picturesque gingerbread cottages while spotting celebrity visitors or indulge in luxury shopping for high-end designs and chic accessories. Don’t forget to try the island’s refreshing signature cocktail, ti punch, as you admire skilled kite surfers gliding gracefully on turquoise waters.

Brightly painted shops and charming pastel buildings greet you as you step into Philipsburg, the lively heart of Dutch St. Maarten. Nestled near the harbor, this vibrant town blends history and modern flair. Famous Front Street invites visitors to savor the Caribbean spirit with local Creole flavors, chic boutiques, sparkling jewelry shops, and energetic casinos. Whether you’re looking to explore or unwind, this cheerful island hub offers something for everyone.

Escape to the island haven of Jost Van Dyke, a treasure trove of possibilities packed into just eight square miles. Discover the serenity of Diamond Cay's national park, home to unspoiled landscapes that ignite the adventurer in you. Let your worries drift away as you snorkel in the crystal-clear waters of Sandy Spit, dancing among colorful sponges and elegant angelfish. Fancy a touch of thrill? Take the helm and navigate your own boat through the legendary Sir Francis Drake Waterway, feeling the freedom of open waters. As evening falls, relax with a drink in hand on a quiet beach, marveling at the gentle glow of your Windstar ship anchored in the harbor—a perfect end to an unforgettable day in paradise.

Enjoy the surreal underwater dance of the Barrier Reef as your ship glides toward the breathtaking sanctuary of Prickly Pear Island. Famous for its thorny yet charming prickly pear cacti, this uninhabited gem offers beautiful beaches, a lively bar, and exciting water sports for those ready to dive into adventure. Nearby, explore the stunning geological wonder of The Baths. This natural formation of massive boulders creates secluded grottoes, shimmering pools, and tunnels waiting to be discovered. For a day of natural beauty and unforgettable exploration, this stop is a dream realized.

Witness the grandeur of El Morro fortress, a UNESCO World Heritage Site standing proudly in San Juan. From the comfort of your luxurious small ship, marvel at the array of colorful colonial architecture as you dock right in the heart of the historic Old San Juan. Adventure and charm unfold just steps from your floating retreat.