The best hotels take you somewhere. They transport you, taking you to another plane, another dimension of comfort, serenity and experience.
The best historic hotels take you to another time — by a carefully curated cocktail of history, luxury and authenticity.
The Caribbean has an impressive portfolio of historic properties — some that have always been hotels, others that have taken historic buildings and meticulously transformed them into havens of hospitality.
From The Bahamas to Antigua, you can find beautiful historic hotels across the Caribbean, all with that rare ability to take places centuries old and make them, well, timeless.
Graycliff, The Bahamas Centered around a mansion built in 1740 by legendary pirate John Howard Graysmith, Graycliff is the crown jewel of historic downtown Nassau, with one of the Caribbean’s most iconic restaurants and a boutique hotel with 20 rooms. It’s the sort of place where luxury abounds, from one of the largest wine cellars on earth to an on-site cigar factory and an exquisite chocolate factory. (Churchill even stayed in the property’s popular pool cottage). The rooms are spacious, with grand bathrooms and Bvlgari amenities, and the service is sublime. It’s a hotel that should be on the bucket list of every Caribbean aficionado — and one of the region’s truly special places.
The Admiral’s Inn and Gunpowder Suites, Antigua Historic Nelson’s Dockyard, the old stomping ground of Admiral Horation Nelson in the late 18th century, is the newest UNESCO World Heritage site in the Caribbean, and it’s home to this boutique jewel. The main building of the Admiral’s Inn dates back to 1785 when it was used as a pitch and turpentine store house, and the remainder of the property is expertly infused into the area, with the Gunpowder Suites particularly lovely, led by the deluxe gunpowder suite. (Don’t miss a drink at the lobby bar).
Sweetfield Manor, Barbados One of the best-kept secrets in Barbados, this historic estate was built in the early 1900s by Waldemar Hanschell, best known as the founder of Barbados’ popular Cockspur Rum. Set in the heart of Barbados’ Garrison UNESCO World Heritage Site, Sweetfield Manor is a wonderfully restored, endlessly charming place to stay, with a standout culinary program, a yoga deck, a lushly-landscaped pool and 10 beautiful guest rooms.
Round Hill, Jamaica For a hotel that’s part-owned by Ralph Lauren (who designed the rooms), this boutique Jamaica gem somehow remains something of a well-kept secret. Round Hill, which opened its doors in 1952, has managed to retain its timeless ambience, instantly transporting you to the dawn of the jet-set age the moment you ride down the hill to the lobby. And history is at the core of this place, where boldfaced names from half a century have all stayed, from John F. Kennedy (yes, you can stay in his villa) to Oscar Hammerstein.
Casas del XVI, Dominican Republic The five-hundred-year-old Colonial Zone of Santo Domingo is just starting to get its spot in the limelight, but in-the-know travelers have long fallen in love with its historic charm. And Casas del XVI, with rooms scattered across a collection of six gorgeously restored homes all dating to the 16th century, is the quarter’s luxury leader, with jaw-dropping design that is unique to each home.
Hodelpa Nicolas de Ovando Set across three “houses” in Santo Domingo’s aforementioned Colonial Zone, this hotel is said to be the first building in Santo Domingo dating back to 1502. It’s got 97 rooms (four of which are suites), and a sprawling campus that includes a pool, a terrific hotel bar, a restaurant and, of course, modern amenities like Wi-Fi.
The Hermitage, Nevis The tiny island of Nevis is one of the Caribbean’s richest historical destinations (one that has been in the spotlight of late as the birthplace of Alexander Hamilton). But its leading historic inn is The Hermitage, a classic Caribbean plantation inn set around what is the oldest extant wooden house in the Caribbean, dating back to 1670. There’s a mix of places to stay, from colorful gingerbread cottages to hillside rooms to a private villa.
Half Moon, Jamaica When Queen Elizabeth II came to Jamaica with Prince Philip in 2002, this is where she stayed. The hotel, which dates back to 1954, represents the pinnacle of Jamaican hospitality, a luxurious, timeless portal to another age, where elegance and refinement rule the day. And while Half Moon will soon debut a dramatic new addition to the property called Eclipse, it remains one of the region’s truly legendary places to stay, particularly its beachfront West Cottages, which have housed a who’s who of the 20th century (and even provided scenes for the James Bond film Live and Let Die).
Hotel El Convento, Puerto Rico Puerto Rico’s historic capital of Old San Juan remains one of the Caribbean’s richest cultural destinations, and the old quarter is home to one true luxury hotel: Hotel El Convento, a 58-room stunner set in a former convent dating back to 1646. True to its origins, it remains a quiet sanctuary in the heart of Old San Juan, with elegant rooms and the amenities of a far larger hotel.
Fort Young, Dominica The 70-room Fort Young is the heartbeat of Dominica’s capital, Roseau. It’s the place to meet, the place to be and one of the island’s town squares (even more so since it almost single-handedly launched Dominica’s tourism comeback after Hurricane Maria). Set on a site that dates back all the way to a French fort from 1720, it’s a refreshing amalgam of history and modernity. And it’s about to get even better, with 60 new rooms called the Fort Collection soon to make their debut in time for the hotel’s 30th anniversary.
Nisbet Plantation Beach Club Only one of Nevis’ iconic plantation hotels is actually set on the beach: the Nisbet Plantation Beach Club, set around a sugar plantation that dates back to the late 18th century. With an elegant, manicured property spanning 30 acres, it’s a hotel that rather deftly marries historic ambience with barefoot beach luxury.
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