Colonial history in San Juan. Piña coladas on a private island. High-end shopping in Bridgetown. Nineteen nights on Queen Elizabeth bring all kinds of Caribbean adventures and plenty of sunshine.

This 7-night sun-drenched voyage departs from San Juan and docks the next day in Tortola, one of the most beautiful of the British Virgin Islands. Next, spend a day sailing to Bridgetown, Barbados, a sleepy beach town with the elegance, adventure (and breathtaking vistas) of a luxury resort.

Enjoy a once-in-a-lifetime experience on a Caribbean cruise aboard Norwegian Pearl. Take in the beautiful turquoise waters and the laidback Caribbean vibes on Long Bay Beach in Tortola. Greet the green sea turtles and colorful fish as you snorkel the turquoise waters of Turtle Cove, in St. Thomas. For stunning views, take a cable car ride to the peak of Mount Isabel de Torres in Puerto Plata.

Soak in the best of paradise on this round-trip cruise from San Juan on Norwegian Epic. In St. John’s, see the baroque towers of St. John's Cathedral and visit the historic Fort James and the Antigua Lighthouse. Stroll Bridgetown’s inviting beaches of Carlisle Bay or tour one of the popular rum factories.

Join in the festive fun and games on board as you celebrate Christmas in the Caribbean sunshine. Then, enjoy a New Year’s Eve to remember, counting down to midnight as you sail toward New York.

Cruise through the Greater Antilles discovering magical places that fell off the map and tiny gems that were never on it in the first place. Skip the crowds of Montego Bay and Ocho Rios and head instead for the silver screen beauty of Port Antonio, "discovered" by Errol Flynn and then long forgotten. Enjoy the retro-Caribbean vibe of Grand Cayman and the undersea wonderland of La Romana.

The shores of Central America and the Caribbean await on this voyage. From tree-lined beaches in Montego Bay to Mayan ruins in Belize, you’ll find a little slice of paradise in every port you visit.

Caribbean beaches, vibrant tropical fish, and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals paired with the company of your new Windstar family. Relive history while sailing aboard a former America's Cup competition sailboat or cook up delicious French meals with a certified chef in Grand Case outside Philipsburg, St. Maarten.

Depart from San Juan, a city alive with vibrant hues and island rhythms, on a 7-day journey through the Caribbean. In La Romana, Dominican Republic, exotic landscapes and hidden caverns await -walk the mesmerizing Cueva de las Maravillas or savor authentic Dominican flavors as music fills the air. Sail onward to Oranjestad, Aruba, where pastel facades meet crystal-blue waters. Stroll lively streets or explore rugged coastlines dotted with wind-swept cacti under sunlit skies.