Puerto Rico’s 500-year-old capital is a history buff’s dream come true. The Spanish settled this harbour as a New World home base, and that influence is still evident, from the fortress walls lining the coastline to the rainbow of colonial buildings along narrow streets. Venture further out from the old town and nature unfolds. You can scale high into the jungled mountains of El Yunque Forest, or keep to the foothills on a riverside horse ride. If despacito is more your speed, pick a pristine beach and recline with a cod fritter and rum drink in hand. San Juan cruises give you the perfect outpost to dial up or dial down your holiday.

Puerto Plata is the Dominican Republic’s oldest city in the north and a tourism pioneer. Nestled by the ocean with a mountainous backdrop, the city offers a lively pier, which is known as the Malecon, colourful shops and opulent homes from the 1800s. The city is famous for Parque Independencia (also known as Parque Central), a park fringed by royal palms and Victorian architecture. In Puerto Plata, you can hop on a cable car for sky-high views, take a tour of the local cacao farms and buy some of the clearest amber in the world.

Nestled right between Montego Bay and Ocho Rios, Falmouth is the perfect backdrop for discovery in Jamaica during your cruise – and there’s lots to do there. For a relaxing ride along the shoreline, hop on a horse in Chukkah Beach. Cruise to Falmouth and head to the Water Square and jam with the locals to live reggae. Culture cravers can get their fix during high tea at the historical Good Hope Estate overlooking the Queen of Spain Valley. And a trip to Falmouth wouldn’t be complete without chowing down on fiery jerk chicken and rum cake, two local favourites.

Grand Cayman is where the high life meets island life. This international banking haven is as much known for award-winning beaches as for the flocks of celebrities and high rollers that frequent them. You can sip Cayman Mama’s while rubbing shoulders with the global glitterati. During your Grand Cayman cruise, you can snorkel with stingrays in Stingray City. Treat your inner foodie at eateries established by acclaimed top chefs like Michael Schwartz, or chow down on conch fritters by the seashore. You can even soak up some rays at one of the beaches voted best in the world, Seven Mile Beach. And do it all in the same day.

While in Tampa, be sure to stroll through the historic Ybor City, full of restaurants, shops and bars, visit the Busch Gardens theme park or explore the Salvador Dali Museum in St. Petersburg. This metropolis never stands still.