The oldest port city in the Americas continues to enchant travelers with new openings, not to mention warm Caribbean breezes, Spanish-colonial mansions, and Afro-Cuban rhythms at lounges like La Vitrola. JetBlue launched nonstop service from New York’s JFK in 2012 and has just added a new daily route from Fort Lauderdale, FL. Clued-in cruise lines have been stopping here for years, and luxury hoteliers are angling for real estate.
On the cusp of the five-year anniversary of the 7.0 earthquake that decimated this western Caribbean island, Haiti is poised for a phoenix-like rise from the rubble. In Port-au-Prince, tent cities have given way to new hotels, including a 175-room Marriott slated to open in early 2015. A push by the tourism department has inspired planned resorts and beautification projects in the southern port of Jacmel and nearby island of Île-à-Vache.
Havana, Cuba: Cuba was Travel + Leisure’s destination of the year in 2015, but the hype isn’t over yet. President Obama’s historic visit in March, which marked the first time a U.S. president walked on Cuban soil in 88 years, was just a prelude for all that’s to come for this once closed-off Caribbean isle.
Despite the island’s lethargic economy, there’s been a big wave of investment in high-end tourism, spurred by a law encouraging wealthy Americans to reduce their tax bill by spending money here. Hedge-fund billionaire John Paulson (who sees the island becoming the “Singapore of the Caribbean”) owns the just-opened Condado Vanderbilt in San Juan, as well as the St. Regis Bahia Beach an hour east of town.
St. Vincent and the Grenadines, the Caribbean: As in the rest of the Caribbean, prices and crowds drop in the Grenadines during the late summer. Rain is a constant threat in August, but that just means the island will be at its most lush. Embrace the glamorous lifestyle by island-hopping via yacht, or pick your favorite and stay awhile.
Newport, RI: Thanks to the mansions along the Cliff Walk, and the hotels that have their own pedigrees (like the Vanderbilt Grace Hotel, built as a summer home by a certain famous family in 1909), this Rhode Island enclave impressed readers with its history, stately architecture, and looky-loo people watching.