The Caribbean islands are known as the home of sandy beaches and gorgeous landscapes, but they have so much more to offer. Rich history and once-in-a-lifetime experiences lie in wait.

On your Caribbean break, why not visit one of the islands’ historic towns? Old towns offer diverse cultures and a potent blend of colonial and modern architecture, introducing you to new cultures and historic buildings a mere stone’s throw from the beach.

Churches, cathedrals, plantation houses and forts are just a few of the tours and sight-seeing activities available in and around Caribbean towns. Old towns are a fantastic addition to your activities, providing an authentic look at these balmy towns and their illustrious pasts.


Roseau, Dominica

Roseau - Caribbean - Oliver's Travels

Roseau – Caribbean – Oliver’s Travels

Though it may be considered the “anti-Caribbean” due to its lack of sandy beaches and resorts, in this case, its anti-Caribbean feel is a distinct pro. If you’re looking for a change from sunbathing and surfing, or have tired of Mother Nature’s beauty, Roseau is exactly what the doctor ordered. Considered one of the friendliest of Caribbean Islands, it is an old town steeped in history and it is home to Botanical Gardens, the Government House, and its very own French Quarter.


St George’s, Grenada

St. George's - Grenada - Caribbean - Oliver's Travels

St. George’s – Grenada – Caribbean – Oliver’s Travels

Venture across town from your Grenada villa to St George’s. The Island of Spice retains its distinct local flavour despite colonisation by the French, Brits, and United States – and a diverse one at that. Organic regions make this a lush and gorgeous place, but it is at Fort George where you will see breathtaking views of the historically rich peninsula. The Grenada National Museum is housed in French barracks from 1704 and former prison, displaying a variety of historical items including Carib and Arawak artifacts, sugar processing machines and equipment, and Josephine Bonaparte’s marble bath.


Santo Domingo, Dominican Republic

Santo Domingo - Caribbean - Oliver's Travels

Santo Domingo – Caribbean – Oliver’s Travels

Santo Domingo is the capital and historic centre of the Dominican Republic. A UNESCO world heritage site, it is home to the hemisphere’s first monastery, Monasterio de San Francisco. There you will also find the Americas’ oldest surviving cathedral, Cathedral of Santa María la Menor, which was finished in 1540. Many more 16th Century buildings line the Plaza España, making Santo Domingo a must visit for those looking for history and culture.


Historic Barbados

Barbados - Caribbean - Oliver's Travels

Barbados – Caribbean – Oliver’s Travels

Historic sugar plantation houses are worlds away from your typical sightseeing adventures. Fisher Pond Great House in the lush valley of Sweet Bottom is a classic reminder of the historic sugar plantation culture, while The Sunbury Plantation House dates back to 1660 and offers tours of its historic grounds. At Sunbury you can also sample some local cuisine in its dining rooms and get a taste of the plantation owner lifestyle.

Our collection of properties in the Caribbean is huge. Have a look at it and choose one to complete your perfect holiday. Our concierge team is always ready to help if you need them! 

Photo Credit: Lead Picture courtesy of Jeff Clow. Picture of Roseau courtesy of Shayan (USA) via Flickr. Picture of St George courtesy of Roger via Flickr. Picture of Santo Domingo courtesy of no rain corp. via Flickr. Picture of  Barbados courtesy of Loozrboy via Flickr. 
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