10 heritage cities of the Caribbean

Immerse yourself in the rich culture, history and traditions that permeate the Caribbean’s winding streets and eye-catching architecture with our guide to its heritage cities...

8 mins

History lies strewn across Caribbean cities like fallen coconuts. In Antigua, for example, there is a favourite spot in English Harbour where islanders like to wash their cars. It is a merry scene of music, banter and auto-worship, and the cleaners fill their buckets from a huge water catchment built in the 1740s by the Royal Navy – and still going strong. Look beyond the foam and sponges and there is a wealth of graffiti carved in the plaster by bored sailors. ‘Hacklet, belonging to his majesty’s ship Tavistock 1751’ reads one, while John Webb and Nat Russel from Anglesey felt moved to leave marks to show they visited this beach-fringed island 281 years ago.

Such casual finds are typical of the way the traveller discovers those who once lived here in the Caribbean, from the indigenous Taíno to the dark days of the slave trade. Having spent more than 20 years exploring this region, I’ve grown used to spotting cannon being used as fenceposts and sugar mills ingeniously repurposed as homes, hotel suites, dining rooms and museums – or, even, also on Antigua, as a police training academy.

While I love the sunshine, beaches and rum here as much as anyone, it’s frustrating how that fly-and-flop image masks a formidable heritage. UNESCO recognised this wealth as early as 1982, when Old Havana was one of the first places to be granted World Heritage status. Today there are 21 UNESCO sites across the islands alone, ranging from the colonial architecture of Santo Domingo, the Dominican Republic’s capital, to the colossal but barely-visited Brimstone Hill Fortress on St Kitts.

Such remnants are not just stones and monuments, but a fountain of stories with beating hearts born from the vibrant cook-up of cultures that defines this region. Food for thought and a swim in a warm, turquoise sea – now that’s a proper trip.

1. Cartagena de Indias, Colombia

Plaza de los Coches, Cartagena de Indias, Colombia (Alamy)

Plaza de los Coches, Cartagena de Indias, Colombia (Alamy)

Why go? Founded by the Spanish in 1533, Cartagena was one of the main Caribbean ports from where the colonisers funnelled the riches of the New World back to Europe – and the need to protect this wealth has left it ringed with fortifications including the colossal Castillo de San Felipe de Barajas and 12km of stone ramparts. Granted UNESCO World Heritage status for its historic importance, Cartagena’s also a popular beach stop with a spirited nightlife. To get your bearings head up to La Popa, a 150m hill crowned with a convent that offers a fine city views.

Don’t miss: The walled Centro Histórico with its lattice of cobbled streets and flower-filled plazas where you can relax in the shade nibbling cocada de guayaba (guava with coconut) sweets. Visit the Museo del Oro Zenú for a glimpse of the glistening gold treasures the Spanish were seeking and the Palacio de la Inquisición to see how they brutally maintained their power.

Local flavours: Like coffee? Rum? Chocolate? Ice cream? Cartageneros adore their food and drink and you can learn about all of these and more on a half-day tasting tour with Cartagena Connections. Or join a cooking class to make typical dishes such as crab carimañolas (stuffed yuca fritters) and cassava-coconut cake.

Our tip: Colombia has the greatest bird diversity in the world. A convenient way to appreciate this natural splendour is at the Aviario Nacional in Barú, a 50 minute drive south. The seven hectare aviary is arranged in three ecosystems with 190 species to spot.

2. Santo Domingo, Dominican Republic

Alcazar de Colon at night, Santo Domingo, Dominican Republic (Alamy)

Alcazar de Colon at night, Santo Domingo, Dominican Republic (Alamy)

Why go? Founded in 1496 by Bartholomew Columbus, Santo Domingo was the first city in the New World and has an abundance of churches, fortifications and museums to prove it. Nearly everything to see of historic importance is parcelled up in the 12 blocks of the Zona Colonial on the west bank of Río Ozama. Top of the bill is the Catedral Primada de América, completed in 1540, while the Museo Alcázar de Colón was once the powerhouse of the island’s first governor, Diego Columbus (Christopher’s eldest son). In the warm evenings, these ancient streets come alive with bars offering happy hours and live music; a cool Presidente beer slips down very nicely.

Don’t miss: In the city’s leafy residential district of Gazcue, the Plaza de la Cultura is home to the country’s national theatre, library and several museums. Make a beeline for the Museo del Hombre Dominicano for its insights into the island’s original inhabitants, the Taíno, while the Museo de Arte Moderno features works by its foremost 20th century artists.

Local flavours: The Malecón, the city’s long seafront boulevard, is where Dominicans grab a breather and enjoy some nightlife. Meanwhile, in the Zona Colonial there are free dance shows in Plaza de España on Friday and Saturday evenings; on Sundays the ruined stone walls of the Monasterio de San Francisco resound to a live band playing merengue and salsa.

Our tip: The seaside isn’t the only place to relax in this lively city. In the Arroyo Hondo district you can stroll around the largest botanical gardens in the Caribbean. Covering 2 sq km, it displays flora from across the island and has an arboretum that houses more than 1,500 species of tree.

3. Fort-de-France, Martinique

View from the sea of houses on hillsides in Fort-de-France, capital city of  Martinique (Shutterstock)

View from the sea of houses on hillsides in Fort-de-France, capital city of Martinique (Shutterstock)

Why go? Martinique’s capital is a full-on French port complete with mega-cruise ships, traffic congestion and a firm belief in the importance of lunch. Gallic formality blends with laidback Caribbean rhythms to create a vibrant and at times dishevelled mood. The Place de la Savane is a large rectangular seafront park dominated in its south-east corner by the haughty 17th-century Fort-St Louis, which is still used by the navy – some sections are open for tours. The heart of the city’s heritage lies between the park and Rivière Madame, an intense grid of streets centred on the Gothic Revival Cathèdral St-Louis, built in 1895 using an iron frame to withstand natural disasters.

Don’t miss: Bibliothèque Schoelcher, a flamboyant building on the north-west corner of La Savane that was constructed for the 1889 World Exposition in Paris and then shipped here. It still functions as a free-entry public library and the ornate interior features wrought iron pillars, decorative tiles and the names of French literary greats writ large on the walls.

Local flavours: The French restaurants in Martinique can be disappointing compared to those in mainland France so save your euros and enjoy a picnic in La Savane where there is even a small beach. Here you are never far from a pâtisserie, bien sûr, and you can pick up island fruits such as mangos, pineapples and the figue pomme (a small, sweet banana) in the charming Marché Lafcadio Hearn.

Our tip: Take the 15-minute ferry ride from the pier near Pointe Simon south to Anse Mitan, a popular seaside spot where you can grab a swim then enjoy some ouassous flambés au rhum vieux (shrimps flambéed in aged rum) at a toes-in-the-sand beach restaurant.

4. Willemstad, Curaçao

Colourful Buildings attracting tourists from all over the world to Willemstad, Curacao (Shutterstock)

Colourful Buildings attracting tourists from all over the world to Willemstad, Curacao (Shutterstock)

Why go? With its picturesque UNESCO World Heritage-listed waterfront, brightly coloured gabled buildings and stores selling Gouda cheese and Delft pottery, Willemstad appears to present a classically Dutch scene. In fact it is much more interesting thanks to Curaçao’s cultural diversity – the island is home to over 50 nationalities and most residents speak English, Dutch, Spanish and Papiamentu (Creole). Easy to walk around, the city is split into two parts, Otrobanda and Punda, by the Sint Annabaai channel that is spanned by a swing bridge lit up at night. Visitors can respectfully explore this diverse heritage further at the Mikvé Israel-Emanuel, the oldest continuously used synagogue in the Western hemisphere, and the Museum Kurá Hulanda, which documents the island’s ties with West Africa through slavery.

Don’t miss: A stroll in the Pietermaai district, in the east of the city, which has many fine Dutch 18th and 19th century buildings and doesn’t get swamped with cruise ship visitors. There are also boutique hotels and small restaurants worth returning to for dinner; try Mosa, which offers sharing plates featuring local shrimp, octopus and ceviche.

Local flavours: Plasa Bieu is a casual, lunch-only former market in Punda serving hearty stews and island specialties like funchi (polenta) and cactus soup. Or book a half-day Caribbean cookery class with cheery Dutch chef Helmi Smeulders.

Our tip: Willemstad is flat so cycling is a lovely way to explore – Art Now Tours offers insightful guided rides to see the vivid street art of Punda. 

5. St George’s, Grenada

Panoramic view of the colourful city of St. Georges, Grenada (Shutterstock)

Panoramic view of the colourful city of St. Georges, Grenada (Shutterstock)

Why go? Sprinkled over a promontory on the island’s south-west coast, the colourfully painted buildings of St George’s make a striking tableau as they circle around a well-protected harbour. Exploring inevitably means hiking up and down hills – the view from Fort George, built by the French in 1705, is worth the effort, along with a look at St George’s Anglican Church, dating from 1825, which has bravely defied numerous hurricanes. The Grenada National Museum, on the corner of Young and Monckton Streets, is a modest affair so combine it with a visit to Market Square – Saturday morning is the prime time to appreciate the island’s riches including the fruits and spices for which Grenada is famed.

Don’t miss: Love chocolate? Grenada now has five artisan producers and you can learn all about this moreish confection at House of Chocolate, which combines a small exhibition with a yummy café and shop.

Local flavours: St George’s is the sort of place where you should sit back and watch Grenadan life go by – preferably with a cold local beer and some freshly grilled fish in front of you. A top spot for this is the Carenage waterfront promenade, where Sails Restaurant has harbour views and a menu that glides confidently from tuna salad to goat roti and homemade ice cream.

Our tip: Grenada regularly wins medals at the Chelsea Flower Show and several gardens that send blooms, such as Hyde Park and Smithy’s, are in the hills close to St George’s. Visits are by appointment and can be arranged via Caribbean Horizons.

6. Bridgetown, Barbados

There are beaches in walking distance from central Bridgetown (Shutterstock)

There are beaches in walking distance from central Bridgetown (Shutterstock)

Why go? Cheapside, Milk Market, Wellington Street... There’s a familiar ring to the street names in this easy-going waterfront capital graced with splendid neo-Gothic Parliament Buildings, an inner harbour known as the Careenage and the Garrison Historic Area, which has been declared a UNESCO World Heritage Site for its ‘outstanding British colonial architecture’. The city centre is easily explored on foot, taking in notable landmarks such as the veranda-ringed Mutual Building, erected in 1895, and National Heroes (formerly Trafalgar) Square. Tucked away on the south side of Chamberlain Bridge, the 1893 Blackwoods Screw Dock is the oldest surviving ship-lift in the world, while the nearby dazzling sands and turquoise waters of Brownes Beach may prove irresistible. For a sense of the island’s past, tour the Barbados Museum and George Washington House (where the future United States president stayed in 1751) in Garrison Savannah, which lies 3km to the south.

Don’t miss: A day at the races. All island life comes to the Garrison Savannah track, where horses have been running since 1845. Meetings are generally held on Saturdays.

Local flavours: Try some Bajan dishes such as fried flying fish, pepperpot (a spicy meat stew with cassareep and cinnamon) and coconut cream pie at Brown Sugar, a garden courtyard restaurant near Garrison Savannah that offers a bountiful buffet lunch (brownsugarbarbados.net).

Our tip: Barbados has a trusty network of blue-and-yellow public buses that provide a cheap and entertaining way to travel in and out of the capital. Pay as you board with Barbados dollars.

7. Georgetown, Guyana

Guyana’s Mashramani festival (Alamy)

Guyana’s Mashramani festival (Alamy)

Why go? English-speaking Guyana produces excellent rum and its engaging capital comes scented with sweet smells wafting across from the Diamond Distillery, which is set on the east bank of the Demerara River (tasting sessions available). The national capital has some attractive buildings, not always in the finest condition, that reflect its British and Dutch heritage – the latter’s talent for engineering is manifest in numerous canals and a sea wall that runs along the coast for 450km. St George’s Cathedral, built in 1892 and one of the tallest wooden structures in the world, is the flagship photo op while cricket fans will want to see the historic Bourda ground and its modern successor, Providence Stadium. Save time, too, for the National Museum and the Walter Roth Museum of Anthropology, which is devoted to the country’s indigenous peoples.

Don’t miss: A sunset cruise on the Demerara River, passing under Harbour Bridge to visit mangroves and banks rich in birdlife including egrets, herons, kites and sandpipers (book via wilderness-explorers.com).

Local flavours: Run by chef Delven Adams, the Backyard Cafe serves healthy, fresh, organic Guyanese food in a casual setting; market tours and cookery classes are also available.

Our tip: Head to the free-entry Botanical Gardens, which a good place to look for some of Georgetown’s 200 bird species, including Blood-coloured Woodpecker, macaws, parrots and great horned owls; sightings are optimum at dawn or dusk.

8. San Juan, Puerto Rico

Beautiful summer afternoon in old San Juan (Shutterstock)

Beautiful summer afternoon in old San Juan (Shutterstock)

Why go? Founded in 1521, San Juan is the gateway to the compelling fusion of Hispanic, US and Caribbean cultures that is Puerto Rico. Don’t be put off by its heavy gearing to the cruise-ship market – this exuberant city wants to party with you and offers plenty to enjoy, from a battlemented historic core to arty neighbourhoods and fun-loving high-rise beach resorts.

Don’t miss: Old San Juan, a gorgeous ensemble of Spanish colonial buildings in bold colours with rampant flowers and blue-cobblestoned streets. It is set on a headland at the end of a peninsula and protected by the mighty Castillos San Felipe del Morro and San Cristóbal, both open for tours

Local flavours: No visit to Puerto Rico is complete until you’ve tried some mofongo (mashed fried plantains), lechón asado (spit-roasted pork) and a piña colada or two. Spoon offers various foodie experiences including a cooking class that begins with a market visit, or take things easy on an evening cocktail tour of Old San Juan

Our tip: Puerto Ricans have boundless energy and creativity. For a taste, head to the arty neighbourhood of Santurce, which has an array of striking murals, cutting-edge galleries and the sophisticated Museo de Arte de Puerto Rico. Tours can be arranged through theartwalkpr.

Further afield: Puerto Rico’s second city, Ponce, lies 75km south-west of San Juan on the south coast and is well worth some time. The 19th century sugar boom brought great wealth that resulted in a neat grid of streets endowed with a colourful parade of colonial, Art Nouveau and Art Deco buildings. Crowning this, the Museo de Arte de Ponce houses a thrilling and unexpected collection that includes major Pre-Raphaelite works by artists such as Frederic Leighton and Edward Burne-Jones.

9. English Harbour, Antigua

English harbour and Nelsons Dockyard in Antigua and Barbuda (Shutterstock)

English harbour and Nelsons Dockyard in Antigua and Barbuda (Shutterstock)

Why go? On the island’s south coast, this restored naval base is a laidback mix of heritage buildings, waterside bars and restaurants, and a sheltered harbour that is at the heart of Antigua’s long-standing love affair with sailing. Horatio Nelson declared it a ‘vile spot’ when stationed here in 1784 but today his name graces the UNESCO-listed Nelson’s Dockyard, home to an absorbing ensemble of Georgian-era buildings and a marina bristling with vintage sailing boats and immaculately kept superyachts.

Don’t miss: Housed in the former naval officers’ house, the well-presented Dockyard Museum brings the past to life through minutiae – such as a bone button and trading beads used by slaves – and gives insights into Nelson’s life, including his death mask.

Local flavours: For over 30 years Antiguans have been holding a popular Sunday afternoon barbecue and party up at Shirley Heights, a military post and signal station with a lofty view over English Harbour. The fun starts with steelpan music then local bands take over after the sun sets, with cheery chefs dishing up jerk chicken and grilled fish, and drinks served in the 1791 Guard House (shirleyheightslookout.com).

Our tip: Nelson’s Dockyard National Park has kilometres of coastal hiking trails while the English Harbour Commonwealth Walkway – for now, still a work-in-progress – links up its monuments and sites. When it’s time for a swim, head to the gentle waters of Galleon Beach or Pigeon Point Beach where you may well be joined by a passing turtle.

10. Paramaribo, Suriname

Wooden church in Nieuw Amsterdam village in Suriname (Shutterstock)

Wooden church in Nieuw Amsterdam village in Suriname (Shutterstock)

Why go? Suriname’s road signs, maps, menus and official documents may be in Dutch, but after a few hours in this intriguing country you soon realise what an stimulating mash-up of Amerindian, Asian and Creole cultures it is. Almost half the population live in the capital yet its mood is sultry and benign, a place where commuters travel by motorised pirogue (wooden canoes) and streets bear curious names like Mr F H R Lim A Postraat. The most venerable buildings are constructed from the flat red bricks that were shipped over as ballast while the colossal St Peter and Paul Cathedral was constructed using Surinamese cedar. Start your exploring at Fort Zeelandia, which guards the mouth of the Suriname River and has a comprehensive historical museum, then take a stroll in the nearby Palmentuin, a public park said to have 1,000 palm trees.

Don’t miss: A walk around the historic and remarkably intact Inner City, which was granted World Heritage status for its ‘gradual fusion of Dutch architectural influence with local techniques and materials’. Elaborate wooden houses and a mid-18th century street plan create an extraordinary time capsule that needs no guide – just wander and wonder.

Local flavours: Head for the riverfront cafes and restaurants around Fort Zeelandia for a taste of Surinamese cuisine with its many influences including Chinese, Javanese, Jewish and Creole. De Gadri is an easy-going, mid-price option with dishes that combine chicken and spices with noodles, rice or the root vegetable pomtajer.

Our tip: Take a day trip east to Commewijne, home to historic plantations, then visit Nieuw Amsterdam, a former fort and prison. Travel options include by boat, bike and tuk-tuk. Learn more at orangesuriname.com.

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