Nelsons Dockyard Museun

Beyond the boundless beaches that the region is famous for, the Caribbean has a bounty of historical and cultural treasures that offer a snapshot of the shifting tides of the last few centuries. Mountain-top citadels, naval dockyards, colonial city centres and preserved sugar plantations are among the atmospheric places that help unravel the mysteries of the Caribbean’s past and have been awarded UNESCO World Heritage status.

Laced with tales of European conquistadores, fearsome pirates and Africans stolen from their homelands, each site helps piece together the region’s storied history and the lasting impact that had on the cultures that exist across the islands today. But aside from their historical significance, many of these heritage spots are worth visiting simply for their beautiful old architecture and unparalleled views. Here are seven of the best destinations for an island treasure hunt worthy of Long John Silver.

Time travel in the Caribbean

Nelson’s Dockyard, Antigua

A relic from the island’s days as a British colony, Antigua’s first world heritage site is also the Caribbean’s youngest, having only received official status in 2016. Sheltered between the low emerald hills of English Harbour, the calm waters around Nelson’s Dockyard were the ideal port in a storm. Delightfully chocolate-boxy with cute low-slung roofed buildings set alongside a winding lane and boats bobbing on the sun-drenched dockside, today it’s a picture of nautical bliss that’s a far cry from the atmosphere here in Admiral Nelson’s day, when he described it as “hell-hole”.

Its stone and wood workshops, stores, quarters and boathouse now house a museum, boutiques, cafes, restaurants and a hotel. If it weren’t for the palm trees and the humidity, you could easily be in an old Cornish seaside village. Fortifications in the surrounding hills including Archibald Dow Fort and the Shirley Heights lookout form part of the heritage park.

Bridgetown and its historic garrison, Barbados

Barbados’ garrison has a commanding position on a hilltop plateau just to the east of the old island capital Bridgetown. Constructed in the 1780s, it was the British military headquarters in the Caribbean during the colonial era and, together with the vintage Georgian buildings of Bridgetown, it’s now preserved as a world heritage site. The attractive military buildings – one containing the fascinating Barbados Museum – are arranged around a green terrace that used to be the army drill ground, but now acts as a racecourse. You can visit the national armoury housed inside thick fortress-like stone walls that once stored gunpowder but is now home to a collection of antique weapons including the biggest stash of 17th century cannons in the world and the largest cache of 19th century guns.

Beyond the main grounds, a plantation-style house that was home to US President George Washington has also been kept as a museum. Below its front lawn, 10,000 feet of underground tunnels were recently uncovered, probably dug in 1816 allowing a secret escape route down to Carlisle Bay. You can enter the narrow dimly-lit tunnels and explore a section, tracing fossilized shells and coral in the limestone walls.

Old Havana, Cuba

With unique sights and shrines aplenty, Cuba is peppered with UNESCO World Heritage Sites. In fact it has the most in the Caribbean, making it an excellent destination for cultural explorers. Dubbed the Pearl of the Antilles during the colonial era, by the 17th century Old Havana (Habana Vieja) and its fortifications had become the Spanish’s most important port of call in the Caribbean.

Today its tumbledown Spanish colonial mansions lean precariously on the shoulders of restored buildings painted in bright shades. Cobbled streets lead to atmospheric squares such as Plaza de la Catedral, named for its grand baroque church, and Plaza de Armas, flanked by 16th-century Castillo de la Fuerza and the Palacio de los Capitanes Generales. The palace is preserved as the Museo de la Ciudad where visitors can see its intact 18th-century interiors.

Willemstad, Curacao

Curacao’s capital city is perhaps the Caribbean’s prettiest with colourful Dutch houses lining the waterfront like a quaint canal-side in Amsterdam. The harbour and city centre is UNESCO-listed for its 17th-century architecture and winding alleys that display influences from all over Europe.

Founded in 1643 as a naval base for the Netherlands, the town blossomed into a regional trading hub with several distinct districts separated by a deep channel and crossed via the Queen Emma Pontoon Bridge constructed in 1888 and still swinging open today to let boats through. Willemstad has become a cosmopolitan cultural hub with free regular open-air concerts and museums such as the Kura Hulanda exhibiting pre-Columbian and African artefacts.

National History Park, Haiti

The most impressive citadel in the Caribbean clings to a high rocky crag with dizzying views of Haiti’s picturesque peaks, rivers and coastline. No mere collection of rocks, the Citadelle la Ferrière is splendidly intact with cannons in place and even piles of cannon balls collected on the terraces. It was built and eventually abandoned after the Haitian slave rebellion kicked out the French colonialists in 1804.

This was the Caribbean’s first revolution, and the new rulers wanted a castle with commanding views both inland and out to sea. Together with the baroque skeleton of Sans Souci palace at the foot of the mountain and the buildings of Ramiers, they were the first places to be built by Haitian freedmen and remain as monuments to independence.

Santo Domingo, Dominican Republic

Though old San Juan in Puerto Rico has undeniable charm, the Dominican Republic’s Santo Domingo is the blueprint for all New World cities that came after. The former Spanish colonial city of curling cast iron lamps and cobblestone lanes is more than 500 years old and was founded just after Christopher Columbus arrived.

The city has since succumbed to urban sprawl but the old walled core of the city is in miraculous shape. The Caribbean’s first cathedral, hospital, university and customs house can all be found laid out among its grid patterned streets that are a delight to explore on foot.

Trinidad and the Valley of the Sugar Mills, Cuba

An important stop on Cuba’s heritage trail, UNESCO-listed Trinidad is a true step-back-in-time type of place with peeling Spanish colonial pastel-coloured cottages, terracotta rooftops and sloping stone streets where horse-drawn carts outnumber cars. The quaint town has remained virtually unchanged for centuries and its Plaza Major is perfectly preserved.

Get ready for some hard history lessons next door at the Valley of the Sugar Mills (Valle de los Ingenios), which is UNESCO listed alongside Trinidad for its historical picture of a time when the Caribbean was ruled by the sugar and slave trade. Hauntingly beautiful and deceptively peaceful, visitors can explore the ruins of more than 70 mills, as well as the watchtowers and former slave barracks that dot the valley.

More heritage hotspots…

With seven world heritage sites awarded UNESCO designation for their cultural and historic significance, Cuba is almost stitched with more history than the rest of the Caribbean put together. Once you’ve seen Old Havana and trodden the streets of Trinidad, head to San Pedro de la Roca Castle in Santiago de Cuba, explore the archaeological landscape of the first coffee plantations in the South-east of Cuba, and visit the beautiful old city centres of Cienfuegos and Camagüey. A must-see for anyone visiting Cuba, the stunning Vinales Valley made the UNESCO list for its cultural significance and age-old way of tobacco farming, though the western region’s landscapes of russet fields and hump-backed mogote hills make it a candidate for the Caribbean’s top natural heritage spots, to be covered in another post.

Beyond Cuba, the charming streets of old San Juan in Puerto Rico are a protected cultural site. And if you’re visiting St Kitts and Nevis the colonial fortifications on Brimstone Hill, part of a national park, are not-to-be-missed. Unfortunately, there are currently no heritage sites in the Caribbean that help us understand the islands’ history before Columbus arrived. Remnants of the former resident Carib and Arawak Indian tribes and evidence of ancient Amerindian settlers have been found across the region including pottery, skeletons, spear heads and cave petroglyphs. Archaeological excavations are ongoing – the little Barbuda Research Complex in Codrington offers a glimpse of the important work that’s been done on this front so far.

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