Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports in favor of less-visited destinations like Montserrat.

Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.

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.

Make forever memories as you celebrate Christmas Day and New Year’s Eve on board Queen Mary 2. Arriving in the Caribbean, enjoy time ashore in Saint Kitts and Antigua, among other magical islands.

Your tropical paradise is on the horizon aboard this round-trip cruise from Port Canaveral. Fly high above the jungle floor on an exhilarating zipline then enjoy a refreshing dip in the pools below the breathtaking Damajagua waterfalls in Puerto Plata. In St Thomas, greet the green sea turtles and colorful fish as you snorkel the turquoise waters of Turtle Cove. Jump in a Jeep and head off-road to one of Tortola’s most secluded beaches, Smuggler’s Cove.

Take each day as slowly as you like on this 21-night sailing in the Caribbean that includes captivating ports like Montego Bay in Jamaica, San Juan in Puerto Rico, and Philipsburg in St. Maarten.

Live it up in The Caribbean on a 14-day roundtrip cruise aboard one of our most innovative ships, Norwegian Viva. Sit back and relax in your private beachfront cabana in Great Stirrup Cay, our private island paradise that’s just for you. Enjoy a leisurely bike ride through Philipsburg’s historic sites and take in the spectacular views as you learn about St Maarten’s rich past. Soar above the jungle canopy on a series of ziplines in San Juan.

Your tropical paradise is on the horizon aboard this round-trip cruise from Port Canaveral. Fly high above the jungle floor on an exhilarating zipline then enjoy a refreshing dip in the pools below the breathtaking Damajagua waterfalls in Puerto Plata. In St Thomas, greet the green sea turtles and colorful fish as you snorkel the turquoise waters of Turtle Cove. Jump in a Jeep and head off-road to one of Tortola’s most secluded beaches, Smuggler’s Cove.

Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.

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.

This round-trip voyage from Miami stops at three beautiful islands including Tortola, Bimini (home to our exclusive beach club), and St. Maarten. In St. Maarten, you'll experience a Caribbean melting pot of cultures including Dutch and French (as both nations have their own "side" to the island), plus West African, British, Indian, and Spanish heritage influence the island as well.

Explore breathtaking views on your 9-day cruise aboard the newly refurbished Norwegian Sky. In Curaçao, splash around the warm sea with some friendly dolphins or journey inland to discover the enchanting Hato Caves and then visit a unique Ostrich farm and hang with one of the biggest birds on earth. Uncover the best of Aruba as you soak in fantastic vistas from the California Lighthouse, explore the Aloe Museum and visit the island’s popular Natural Bridge ruins.