Set out on a captivating 11-day sailing from Philadelphia, leaving behind the East Coast skyline for the sunlit allure of the Caribbean. Stop at St. Thomas, where blue waters invite you to snorkel at Magens Bay, explore the charming boutiques of Charlotte Amalie, or simply immerse yourself in the island’s relaxed ambiance. Next, discover the green hills and hidden beaches of Road Town, Tortola - hike up Sage Mountain for sweeping views or trace the coastline by boat.

This 7-night idyllic journey departs from San Juan and docks the next day in St. Maarten. From there you'll head to St. Kitts followed by St. Johns in Antigua - the quintessential paradise lover's paradise - where you'll discover the epitome of a tropical haven. From there you'll dock in St. Lucia, then spend a day sailing to the British Virgin Islands before finally returning to San Juan.

Sail away from San Juan for seven days of pure island enchantment, where each port beckons with promise and charm. Start in Road Town, Tortola, where lush hills and secret coves await - dive into crystal waters where you might see a gentle sea turtle or journey inland to the mystical Baths, where giant granite boulders create hidden grottos.

From capital cities with vibrant cultures to hidden caves, hot springs and island gems, this unforgettable cruise is yours to discover.

Experience sounds, sights and tastes of Miami, then explore the pirate history of San Andrés, with its patchwork coconut groves and rocky beauty. After jungle adventures in Puerto Limon, relax in the lush tropical surroundings of Gatun Lake and marvel at man-made wonder of the Panama Canal.

Enjoy a scenic drive in Road Town, get panoramic views from Sky World, and swim in Cane Garden Bay on this beach tour near Romney-Pier Park.

Sail two days from Miami to the stunning beaches and immaculate vibes of Philipsburg, St. Maarten, followed by the enchanting rainforests and impressive wildlife of Tortola, British Virgin Islands. Awake the next day in St. Croix followed by San Juan and then the silver coasts of Puerto Plata, Dominican Republic. Sail another day to the brilliant Beach Club at Bimini before returning to Miami.

Immerse yourself in stunning landscapes, vibrant cultures, and luxurious serenity on a journey through the Caribbeans idyllic hideaways.

Sapphire shorelines and emerald hilltops dazzle under the Caribbean sun on our exploration from the paradise of Road Bay through St John's striking shoreline to the patchwork peaks of Phillipsburg. Gentle winds escort us onwards to the heritage of Spanish Town, the rhythms of Miami and heart-shaped, heart-stopping Magen's Bay in St Thomas. Pause to browse through pretty French-influenced markets in Terre-de-Haut and Fort-de-France, then watch the sunrise sparkle over lively St Kitts.

Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke.