Top 5 Historic Hotels in the Caribbean

Top 5 Historic Hotels in the Caribbean

Historic hotels in the Caribbean offer an intriguing glimpse into bygone days

By: Mark Rogers
<p>Hostal Nicolas de Ovando in Santo Domingo’s Colonial Zone offers 104 guestrooms. // © 2014 Hostal Nicolas de Ovando</p><p>Feature image (above):...

Hostal Nicolas de Ovando in Santo Domingo’s Colonial Zone offers 104 guestrooms. // © 2014 Hostal Nicolas de Ovando

Feature image (above): The Georgian-style Admiral’s Inn Antigua is named after national hero Admiral Horatio Nelson. // © 2014 Antigua and Barbuda Tourism Authority


While glittering new properties in Caribbean tend to create quite a buzz as they welcome their first guests, there’s another type of accommodation that has been quietly welcoming visitors for many years.

These are the handful of truly historic Caribbean hotels, where guests are more likely to be entranced by the grace of a wooden shutter rather than the availability of in-room cutting-edge technology. These hotels date back as far as the 16th century and can provide a unique dimension to a Caribbean vacation. 

Here are five historic hotels in the Caribbean that each has an authentic historic heritage:

The Admiral’s Inn, Antigua
The Georgian-style Admiral’s Inn in Antigua is named after Admiral Horatio Nelson, one of the country’s national heroes. The hotel was built in 1788 on a prime spot in Antigua’s harbor in what is now called Nelson’s Dockyard National Park. Nelson’s Dockyard has much to offer visitors, including the Dockyard Museum and numerous boutiques and restaurants. The bricks used in the construction of the Admiral’s Inn were originally ballast used by 18th century English sailing ships. The hotel has 14 rooms; for the best views, book your clients into one of the harbor view rooms.

Graycliff Hotel, Bahamas
Graycliff Hotel in Nassau, Bahamas was built in 1666 and was originally an Anglican church and then a Spanish garrison. Flash forward to 1740 when the ruthless pirate Captain John Howard Graysmith — who plundered the seas in his ship, Graywolf — built a mansion on the site. In 1844, the mansion transitioned into becoming an inn, which subsequently hosted famous guests such as Winston Churchill and the Duke and Duchess of Windsor.  

The 20-room hotel is only minutes away from the beach. Infused with proper British ambiance, the hotel is celebrated for its Humidor Churrascaria restaurant, the cigars available at the on-site Graycliff Cigar Company and the delectable treats for sale in the Graycliff Chocolatier shop.

Hostal Nicolas de Ovando, Santo Domingo
The 16th century Hostal Nicolas de Ovando is in Santo Domingo’s Colonial Zone, where travelers can find evidence of the city’s status as the oldest city in the New World on block after block. Hostal Nicolas de Ovando is named after its original owner, Nicolas de Ovando, the first governor of the Americas. Today, the 104-room property is composed of three houses, all with stone walls, hacienda shutters and wrought iron work. During my stay, I was lucky enough to be booked into one of Colonial rooms, which transported me back in time. 

A lively ambiance prevails in this property, which is a meeting place for the movers and shakers of Santo Domingo. La Residence, the hotel’s restaurant, is considered one of the best dining spots in the city. The Cibao Bar in the lobby pours rums from 12 different Caribbean countries and offers a choice of top-notch Dominican cigars.

Hotel El Convento, Puerto Rico
The Hotel El Convento in Puerto Rico’s Old San Juan district dates back to the 17th century, when it was a convent for Carmelite nuns. In 1959, it transitioned into a 58-room hotel in the Spanish Colonial style, from its decorative glazed tiles to its velvet settees. Guests here will be right in the middle of Old San Juan, making it convenient for them to stroll along the cobblestone streets, browsing through shops and discovering restaurants.  

Hotel El Convento is an AAA Four Diamond Hotel. The property has three restaurants onsite specializing in regional cuisine and Spanish tapas. There’s also a modern touch: a swimming pool overlooking San Juan Bay.

Montpelier Plantation & Beach, Nevis
The Montpelier Plantation & Beach on Nevis was constructed in the 1700s and was the location where Admiral Horatio Nelson married Francis Nisbet in 1787. Originally a sugar plantation home, Montpelier Plantation & Beach has 18 rooms, all with ocean views. Guests can explore 10 acres of gardens, take a dip in the mosaic tile pool and arrange for a private dinner in the plantation’s restored sugarcane mill.