Trip Details - AO Trips

Set sail on an unforgettable journey through the sparkling heart of the Caribbean aboard a private Windstar yacht, chartered exclusively for our travelers. This curated, nine-night winter escape in 2027 blends laid-back island charm with sophisticated indulgence, offering a chance to experience the Caribbean as few ever do – on your own luxurious path through paradise.

The itinerary was crafted exclusively for A-O Trips travelers, providing a once-in-a-lifetime experience that cannot be duplicated on any other cruise. Your cruise comes complete with a wide variety of included drinks and dining options, so you can indulge in everything from morning mimosas to sunset cocktails while savoring gourmet meals.

Your adventure begins in San Juan, Puerto Rico, a city that pulses with rhythm, color and colonial grandeur. Your first night will be spent in your roomy cabin aboard the Windstar Pride while docked in San Juan, enabling you to explore the city at your leisure. Stroll the cobblestone streets of Old San Juan, where Spanish forts overlook the sea and pastel-hued buildings house vibrant boutiques and hidden cafés. As the sun sets on the next day, you will set sail into the moonlit Caribbean.

The first port of call is the British Virgin Islands, where Virgin Gorda welcomes you with its iconic Baths – giant granite boulders forming natural sea pools that are perfect for a morning swim or a relaxing snorkel. From there, you will indulge in a day at sea, with a chance to unwind aboard the ship with spa treatments, island-inspired cuisine and endless ocean views.

Next, the lush volcanic island of St. Lucia awaits. Anchoring in Soufrière, you'll be dazzled by the twin Pitons rising dramatically from the sea. Opt for a scenic tour, venture through the rainforest or indulge in a tasting experience showcasing Creole flavors. As the sun sets, enjoy a magical sail past the Pitons – one of the most breathtaking vistas in the Caribbean.

In Antigua, you will dock in Falmouth, a haven of historic charm and yachting elegance. Browse artisan shops for handmade treasures or explore the island’s 365 beaches. Then it’s on to St. Kitts and Nevis, where the capital city of Basseterre offers a fusion of colonial architecture and vibrant markets. Take a heritage tour, ride ATVs through the countryside or discover panoramic views from a scenic railway.

A highlight of the itinerary is cosmopolitan St. Barts, where chic boutiques, French cuisine and powder-white beaches create a setting that’s both glamorous and relaxed. Enjoy a leisurely day in Gustavia soaking in the island’s unique blend of Caribbean beauty and European flair.

A final day at sea eases you into the conclusion of this luxurious voyage, giving you time to relax, connect and reflect as the ship makes its way back to San Juan. Whether you're savoring fine cuisine during a cooking demonstration, dancing to live music or indulging in a massage as the sun dips into the sea, every moment is designed for delight.

This exclusive Caribbean cruise is more than a winter escape – it's an immersive journey through vibrant cultures, natural wonders and sun-drenched elegance. Join us in 2027 for a travel experience that’s as intimate as it is inspiring.