From $3,699 per person
15 days
Ship: Wind Surf
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Enjoy Windstar’s exclusive Signature Beach Party at Prickly Pear Beach<br />
Day-by-day description of your cruise and cruise activities.
Philipsburg, St. Maarten
Step into Philipsburg, a vibrant town where the charm of pastel-colored buildings meets the buzz of colorful shops. Located on St. Maarten's Dutch side, this bustling harbor town first captured Christopher Columbus's attention in 1493, and it hasn't stopped captivating visitors since. Stroll along celebrated Front Street, where world-class jewelry stores and stylish boutiques sit alongside inviting Creole restaurants. Not to mention, fun-filled casinos make this town the perfect destination for those looking to savor the lively island atmosphere.
Charlestown
In Charlestown, the capital of Nevis, history comes alive. Venture down its charming streets lined with brightly painted Victorian and Georgian stone buildings, each a remnant of its colonial past. Explore the Hamilton Estate ruins, where Alexander Hamilton once roamed as a child. You’re never far from nature’s treasures—Pinney’s Beach, with its golden sands, is nearby, and at night, dedicated volunteers track sea turtles along these serene shores. Stroll Main Street to uncover gems like the Museum of Nevis History, St. Thomas Lowland Church, and the Nevisian Heritage Village. Charlestown offers a perfect mix of culture, heritage, and scenic beauty.
Roseau
Discover the beauty of Champagne Beach, where you can snorkel alongside colorful parrotfish in waters that bubble like champagne. Stroll through the lush botanical gardens, home to over 150 species of plants and the vibrant red-necked Jaco parrots. For the adventurers, an unforgettable hike awaits at Morne Trois Pitons National Park, a UNESCO World Heritage Site. Explore the dramatic Boiling Lake and the raw landscapes of the Valley of Desolation. There’s so much to see and do, you’ll be swept up in the wonder of it all.
Mayreau
Imagine stepping into a tranquil paradise where time slows down and every moment feels like a private escape. With fewer than 300 residents, Mayreau exudes seclusion and charm. Saline Bay welcomes you with its pristine beaches and gentle waters, nestled perfectly between the Caribbean and the Atlantic. This serene anchorage is an ideal spot to indulge in water fun, with easy access to our Watersports Platform. Unplug, unwind, and let the natural beauty surround you.
Les Saintes
Picture a dreamlike Caribbean escape: serene blue harbors dotted with sleek yachts and framed by volcanic landscapes. Relax on beaches where the tall palms sway to ocean breezes. Beneath those clear waters, a captivating marine world awaits, famous enough to inspire Jacques Cousteau. You don’t need to be an expert diver to marvel at the stunning underwater treasures—just bring your sense of wonder and dive into this paradise.
Basseterre
Nestled against lush emerald hills, Basseterre enchants visitors with its charming Georgian architecture and tranquil ambiance. This Caribbean gem radiates a timeless allure, inviting you to explore its heritage and serenity. Just beyond the city's edge lies the majestic Brimstone Hill Fortress, a UNESCO World Heritage Site. Set within a sprawling national park, this historic landmark offers breathtaking vistas and a journey through the island's storied past.
Gustavia
Think of St. Barts as the Caribbean's answer to the French Riviera. This sophisticated island combines stunning beaches with a European flair, creating a playground for the discerning traveler. Wander quaint streets lined with colorful gingerbread cottages, indulge in high-end shopping with duty-free perks, or relax with a local ti punch as the sky fills with kite surfers. With a mix of chic elegance and vibrant charm, this island is your gateway to a truly refined escape.
Philipsburg, St. Maarten
Philipsburg welcomes you with its charming pastel buildings and vibrant atmosphere. Located on the Dutch side of St. Maarten, this lively town blends history with modern flair. Discover its roots dating back to Christopher Columbus’ arrival in 1493, and stroll through iconic Front Street today. Here, you’ll find a delightful mix of Creole restaurants, unique boutiques, elegant jewelry stores, and bustling casinos offering an exciting taste of island life.
Falmouth Harbour
Antigua is a paradise blessed with a beach for every day of the year—365 in total. During your extended stay in port, take your time exploring the pristine coastline and turquoise waters that make this island so captivating. As evening sets in, watch the stars light up the tropical sky. It’s a magical sight residents of distant galaxies might even envy.
Road Bay
Road Bay unfolds like a tranquil retreat with its secluded waters and sugar-white sands, a dream destination for boaters seeking laid-back peace. Dotted with lively bars, charming restaurants, and unique local shops, it offers the perfect mix of relaxation and Caribbean culture. As the golden sun dips below the horizon, the vibrant colors paint the sky for what could be the most breathtaking sunset you’ve ever seen. Sip on a glass of tangy rum punch while listening to the waves in the distance. Nature enthusiasts will find themselves intrigued by the red-footed tortoises, Cuban tree frogs, and green iguanas that call this paradise home. A visit to the nearby Wallblake House, Anguilla’s treasured plantation house museum, offers a glimpse into the island's rich history and charm. This serene escape is perfect for travelers looking to indulge in natural beauty and authentic island experiences.
Soper's Hole
Wander onto the welcoming boardwalk at Pusser’s Landing, nestled in the breathtaking marina of Soper’s Hole. Surrounded by pristine views, watch yachts dance on the water as you take in the inviting charm of this remarkable port. Uncover a quiet, sunlit beach nearby—perfect for pondering stories of pirates, romance, and seafaring adventures from centuries past. As the day winds down, prepare to set sail on a magical, unforgettable evening journey under a canvas of warm sunset hues.
Jost Van Dyke, Great Harbour
Jost Van Dyke may only span eight square miles, but it's overflowing with opportunities for adventure and relaxation. Take a visit to the nearby Diamond Cay National Park for a peaceful escape, or go snorkeling at Sandy Spit to explore a colorful underwater world filled with sponges and angelfish. For the more adventurous, steering your own boat around the Sir Francis Drake Waterway is an experience you won’t forget. After an active day, settle in on the beach with a drink in hand, watching your elegant Windstar ship shimmering in the harbor as the sun sets.
Virgin Gorda / Prickly Pear, British Virgin Islands
A striking natural oasis awaits as your small ship glides through the shimmering waters over the Bank Barrier coral reef, a delicate underwater treasure. Your adventure lands at Prickly Pear Island, an untouched sanctuary sprinkled with prickly pear cacti and home to a relaxing beachside bar and lively water sports. Although uninhabited, this island is perfect for exploring or just soaking up the tranquil beauty of its surroundings. Just a short journey away lies "The Baths," an extraordinary labyrinth of enormous granite boulders forming secluded grottos, crystal-clear pools, and enchanting caves—an unforgettable marvel of nature. Please note: Only guests with pre-arranged Windstar shore excursions can land at Gun Creek.
Gustavia
Nestled in the Caribbean, St. Barts offers a touch of French charm set against pristine, Riviera-like beaches. This chic island invites you to take a leisurely stroll past its iconic gingerbread cottages or indulge in duty-free shopping for high-end designer treasures. Watch kite surfers dance across the waves or savor the quintessential island drink, ti punch, as the breeze carries the allure of paradise your way.
Philipsburg, St. Maarten
Philipsburg welcomes you with its charming pastel-colored buildings and vibrant streets. Located on the Dutch side of St. Maarten, this lively coastal town offers a bit of everything for visitors. Wander along celebrated Front Street to discover unique souvenirs, elegant jewelry stores, and stylish boutiques. Savor authentic Creole flavors at the local restaurants, or step into one of the energetic casinos for some island-style excitement. Whether you're shopping, dining, or exploring, Philipsburg's blend of history and modern luxury delivers an unforgettable experience.
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