Windward Islands Surf & Sunsets

Escape to the warmth and beauty of the Caribbean during seven relaxing days of surf, sand and unforgettable sunsets throughout the Windward Islands. Designed for travelers seeking a refreshing break from everyday responsibilities, this leisurely voyage offers the perfect balance of tropical adventure, cultural discovery and time to simply unwind.

Each island reveals its own distinctive personality, from colorful waterfront villages and peaceful beaches to lush volcanic landscapes and crystal-clear bays. Spend your days exploring charming ports, sampling local flavors or settling into a quiet stretch of sand with the Caribbean Sea at your feet. With no need to rush, the journey invites you to embrace the islands’ easygoing rhythm and enjoy every moment as it unfolds.

The waters surrounding Les Saintes offer an especially memorable setting for exploration. Swim alongside graceful sea turtles, discover vibrant coral reefs and encounter colorful marine life beneath the surface. Guided by experienced diving and snorkeling professionals, guests can explore the remarkable underwater scenery that lies just beyond the island’s dramatic volcanic shoreline.

Those who prefer to remain above the water can discover the islands through scenic drives, sailing excursions, coastal walks and visits to welcoming local communities. Whether your ideal day includes an active adventure or an afternoon spent relaxing beside the sea, every port offers a new opportunity to experience the natural beauty and welcoming spirit of the Windward Islands.

Aboard Windstar, the journey feels as personal as the destinations themselves. The intimate atmosphere, attentive service and carefully curated excursions allow you to experience the Caribbean in a way that larger ships simply cannot provide. Smaller ports, secluded anchorages and unique local experiences bring you closer to the islands while personalized attention ensures that every day feels effortless.

Vacation time is always well spent in the Windward Islands, but Windstar transforms a simple Caribbean escape into something truly memorable. From the moment you step aboard until the final sunset disappears across the horizon, this seven-day voyage offers the freedom to relax, explore and reconnect with what matters most.