Price Per Night:$130.84 (USD) (based on double occupancy, for comparison only)
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.
Price Per Night:$299.93 (USD) (based on double occupancy, for comparison only)
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.
Price Per Night:$102.52 (USD) (based on double occupancy, for comparison only)
This 21-night voyage on Queen Elizabeth gives you the chance to revel in life on board, as well as soak up plenty of Caribbean sunshine with port calls in Barbados, Jamaica, and Saint Lucia.
Price Per Night:$107.42 (USD) (based on double occupancy, for comparison only)
Dusty hilltops. Verdant jungles. Sugar white sands. This 33-night sailing allows you to explore natural beauty across the Americas, plus the manmade wonder that is the Panama Canal on the way.
Price Per Night:$399.86 (USD) (based on double occupancy, for comparison only)
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.
Price Per Night:$209.14 (USD) (based on double occupancy, for comparison only)
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.
Price Per Night:$139.00 (USD) (based on double occupancy, for comparison only)
Depart Miami and sail 2 days to the beautiful beaches of Saint Maarten, Philipsburg, followed by the ancient ruins and glowing lagoons of Tortola, British Virgin Islands. The next day you'll awake in Basseterre, St. Kitts followed by the epitome of paradise with top-of-the-line everything - St. John's, Antigua. Finally, sail 2 days to the private Beach Club at Bimini before returning to Miami.
Price Per Night:$285.64 (USD) (based on double occupancy, for comparison only)
Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating.
Price Per Night:$139.00 (USD) (based on double occupancy, for comparison only)
This 7-night Thanksgiving voyage departs from San Juan, arriving the next day on the shores of Tortola, BVI. The journey continues with a stop in St. Kitts & Nevis, followed by Antigua, a true paradise for any traveler. From there explore the waterfalls and lagoons of Castries, St. Lucia before spending Thanksgiving at sea. Finally, wake up to the beauty of St. Thomas before returning to San Juan.
