26 Historic Hotels in the Caribbean Where You Step Back in Time

The Caribbean is filled with storied places. Former colonial mansions and centuries-old inns. Sugar plantations and oceanfront estates that have watched over harbors for generations. Some of these hotels have been hosting travelers for decades. Others have transformed elegant heritage buildings into hideaways for a new era.

They’re places where the past is never far away — where old walls, worn floorboards and intricate architectural details meet cool pools, smart cocktails and easy, breezy island luxury.

These are 26 historic hotels across the Caribbean where charm, beauty and a sense of history live on.

British Colonial Nassau — Nassau, Bahamas

The property was first built back in 1924, overlooking Nassau Harbor. And this grand hotel has long been a symbol of Bahamian elegance. Its stately façade faces the water like a sentinel, watching as ships, then planes, transformed the way people arrived. Inside, sweeping staircases and lofty ceilings reflect the ambition of another era, when travel was slower, more deliberate, and wrapped in ceremony. After years of meticulous restoration, the hotel has reemerged with a refreshed character — pairing architectural grace with contemporary design and service. It’s once again the heartbeat of Bay Street — and it’s better than ever, from its beautiful beach to its outstanding culinary program.