An expert cruise guide to the Caribbean

From prehistoric rock art sites to state-run musical theatres, the Greater Antilles is no Caribbean cliché. Covering a staggering 90 per cent of the West Indies, this quintet of islands has given the world more than most realise.

The Cayman Islands commercialised scuba diving, Cuba invented salsa, Jamaica birthed the Rastafari movement and the Dominican Republic designed the first city grid system, while Puerto Rico’s indigenous Taino created the barbecue.

Slowly but surely the Greater Antilles is disentangling its Spanish, French, English and American colonial histories and revisiting its African and indigenous roots, which have shaped everything from its soul-stirring music to its finger lickin’ cuisine.

THE CAYMAN ISLANDS
Protruding through Caribbean waters, this trio of underwater mountains was first spotted by Christopher Columbus in 1503 when his ship blew off course on his return from Panama in Central America.

Despite coming under British rule in 1670, the Cayman Islands – named after the marine crocodiles that once thrived here – remained largely uninhabited until the 1700s.

But it wasn’t the first time a reptile had inspired a moniker for the archipelago, as Columbus christened the islands ‘Las Tortugas’ after the scores of sea turtles he discovered here. Turtling was a mainstay of the economy during the 17th and 18th centuries, replaced by shipbuilding until the start of the Second World War.

The Cayman Islands’ national motto, ‘He hath founded it upon the Seas’ is a clue to its storied seafaring past that’s writ large across the country. Its Maritime Heritage Trail ticks off no less than 36 archaeological sites across the three islands of Grand Cayman, reef-ringed Little Cayman and Brac. In the capital, George Town, on Grand Cayman, you can see the ramps where mahogany schooners were once launched, cut into rock.

Tethering the capital to Long Point on the island’s western coast is Seven Mile Beach, which is something of a misnomer since it’s only 6.3 miles (10km) long. Caymanian Joanna Boxall – who edits Explore Cayman – has made visiting it part of her Saturday morning ritual. “A stroll on Seven Mile Beach is a wonderful way to start the weekend. The sand is soft and gentle underfoot, there are no rocks, and you can walk and walk for miles.

"If you go early enough, the purple shadows from the casuarina and palm trees shade the beach in a charming and rather magical way, and you can sometimes spot juvenile turtles swimming in the shallows near Government House.”

The turtles aren’t the archipelago’s only charismatic underwater critters. You can also wade waist-deep in gin-clear waters with graceful southern stingrays in their natural environment at Stingray City. The best way to experience this offshore shallow sandbar is from a glass-bottomed boat on a 90-minute tour.

As the sun dips, make your way to Sunset House for sundowners with your toes buried in the sand. “It’s where all the locals go on a Friday evening. The curry is delicious,” says Joanna.

To get to know Grand Cayman’s wilder side, make a pilgrimage to the million-years-old Crystal Caves, which are concealed by an emerald green tropical forest. “They do a Dusk to Dark evening tour on Monday and Friday at 5.30pm,” Joanna adds.

“All the caves are lit up, so it’s really quite special. You can see wonderful stalactites and stalagmites as well as a few thousand fruit bats.”

GET ON BOARD
NCL’s seven-night Caribbean: Great Stirrup Cay and Cozumel cruise aboard Norwegian Prima, return from Port Canaveral (Florida) via Great Stirrup Cay (Bahamas), Montego Bay (Jamaica), George Town (Grand Cayman) and Cozumel (Mexico), departs on December 7, 2025. Fares from £1,038.

Holland America Line’s 14-night Western Caribbean Explorer/Tropical cruise aboard Eurodam, return from Fort Lauderdale (Florida) via Half Moon Cay (Bahamas), Cozumel (Mexico), Belize City (Belize), Mahogany Bay (Honduras), Ocho Rios (Jamaica) and George Town (Cayman Islands), departs on December 8, 2024. Fares from £2,109.

CUBA
This time-warped isle was controlled by Spain for four centuries until its neighbour and longtime adversary the USA briefly took control in 1898.

Cuba made its early fortunes from its fertile plains, cultivating the first tobacco crops in 1531 and enjoying a sugar boom at the turn of the 20th century. The 1800s marked the golden age

of Cuban cigars, during which the capital Havana became home to 1,300 cigar factories. Even today, Torcedores continue to hand-roll the ‘Champagne of Cigars’ in Pinar del Rio province’s Vinales Valley, which is cradled by boulder-like mountains.

The year 1959 marked another major moment in Cuba’s eventful history, when the communist revolutionary Fidel Castro toppled Fulgencio Batista’s military dictatorship, establishing
a socialist state that holds to this day.

Cuba’s delightfully dishevelled capital remains a communist time capsule. Billboards bear revolutionary slogans, while convertibles in Barbie pink and lime cruise its 6.5km sea-spritzed Malecon (esplanade). Save a classic car tour for dusk, when silhouetted fishermen cast their lines and rag-tag musicians serenade passers by.

Primed for unscripted exploration, the charmingly crooked streets of Havana’s 500- year-old historic quarter, La Habana Vieja, are atmospheric at any time of the day. Spilling out across the cobbles are the sounds of Afro-Cuban jazz, Mambo and Cuban son, which Buena Vista Social Club put on the world music map.

The favourite musical haunt of Sue Herrod – a British composer-songwriter who has called Havana home for 25 years – is in the city’s acclaimed fine art museum. “The place I most love to hear live music is in the intimate [state-run] 300-seater theatre tucked away inside the 18th-century building of Museo de Bellas Artes,” she says. “In this gem of a place I’ve heard top Cuban jazz-classical pianist Ernan Lopez-Nussa and the brilliant, unique voice of the Canadian composer- singer-songwriter Rufus Wainwright.”

Leaving central Havana’s crumbling façades behind, graze on vegan-friendly fare in one of Old Havana’s “not-so-curated neighbourhoods,” says Sue. “In Jibaro restaurant you can enjoy dishes that are traditional to the island but with a twist – such as tostones, or twice-fried green plantain – and I recommend their ratatouille and ropa vieja, which is shredded beef or pork in a lightly spiced tomato sauce.”

The restaurant also serves up some inspired cocktails. “My go-to drink predates mojitos or daiquiris and is reckoned to be Cuba’s oldest cocktail,” says Sue. “It’s a delicious mix of aguardiente, lime and honey called canchanchara, but made here, Jibaro-style, with quality Santiago eight-year-old rum.”

GET ON BOARD
Ambassador Cruise Line’s 45-night Cuba and Treasures of the West Indies cruise aboard Ambition, return from London Tilbury via Praia da Vitoria (Azores), Ponta Delgada (Azores), St John’s (Antigua), Basseterre (St Kitts), Havana (Cuba), Santiago de Cuba (Cuba), Ocho Rios (Jamaica), Willemstad (Curacao), Scarborough (Tobago), St George’s (Grenada), Bridgetown (Barbados), Funchal (Madeira), Lisbon and Porto (Portugal), departs on January 9, 2025. From £2,929.

JAMAICA
The Caribbean’s third largest island was settled in the early 16th century by gold-seeking Spaniards, who went on to rule for a century and a half before ceding power to Britain in 1670. Jamaica has survived countless natural disasters over the years, including the great fire of 1704 which gutted its Port Royal City, and a devastating earthquake that tore through the capital, Kingston, in 1907.

Make downtown Kingston’s mural-plastered Water Lane – a modern tribute to the country’s rich musical heritage – your first stop. And don’t miss a pilgrimage to the childhood home and recording studio of Jamaica’s first son – the reggae legend Bob Marley. Now a museum, it’s just a 20-minute taxi ride east.

For lunch on the go, tuck into Jamaica’s most famous street food: jerk chicken, cooked slowly over indigenous pimento wood. Another locals’ favourite, ‘rundown’, is an earthy mackerel stew simmered in a savoury coconut milk sauce, which can also be made into a vegan ‘ital’ (food eaten by Rastafarians) version with butternut squash.

Escape the early afternoon heat in the island’s cooler rainforest-cloaked interior. Luminous lagoons and cascading waterfalls such as the 55m-high Dunn’s River Falls – of Dr No film fame – make this as much of a magnet for aquaphiles as Jamaica’s 1,022km-long coast.

One of the island’s more serene activities involves floating down the jade-green Martha Brae River on a nine-metre bamboo raft, similar to those used to convey sugar to port during Jamaica’s prosperous plantation era.

The river’s course snakes past trees swollen with mangoes, while artisan shops sell homespun souvenirs straight from the banks. And keep your eyes peeled for tailed deer, peacocks and otters.

Close out your day with a soft adventure in eastern Jamaica’s mist-veiled Blue Mountains, where some of the world’s most prized coffee beans grow at a head-spinning 1,800m. Hiking, driving and biking plantation tours call in at historic estates where you can enjoy a cup of single-origin handpicked coffee, paired with views that stretch all the way to Cuba.

GET ON BOARD
MSC Cruises’ 14-night Caribbean cruise aboard MSC Seascape, return from Miami (Florida)
via Puerto Plata (Dominican Republic), San Juan (Puerto Rico), Ocean Cay MSC Marine Reserve (Bahamas), Miami (Florida), Ochos Rios (Jamaica), George Town (Cayman Islands) and Cozumel (Mexico), departs on February 15, 2025, from £1,419.

Celebrity Cruises’ seven-night Grand Cayman, Jamaica and Labadee cruise aboard Celebrity Equinox, return from Port Canaveral (Florida) via George Town (Grand Cayman), Falmouth (Jamaica) and Labadee (Haiti), departs on February 22, 2025, from £519.

DOMINICAN REPUBLIC
The Dominican Republic covers the eastern two thirds of Hispaniola: a Caribbean island of many superlatives, including the first paved road in the Americas and the Western hemisphere’s oldest standing cathedral. In 1492, the Dominican Republic became the first Spanish colony in the New World; the French colonised neighbouring Haiti 130 years later.

Laid out in a checkerboard pattern that became the blueprint for town planners across the Americas, the Unesco-crowned colonial zone of Santo Domingo – the Dominican Republic’s capital – feels like a living museum. Ruth Pion’s Hidden History – A Decolonial Tour is designed to scratch beneath the surface of the city’s restored Baroque architecture and give a voice to the island’s indigenous peoples and Afro- Dominicans.

A social researcher and the founder of educational project AfrohistoriaRD, Ruth says: “The second stop of the 90-minute walking tour is one of the most impactful. The 16th century gate of the Royal Shipyards was built by enslaved Africans, who were auctioned at La Negreta.”

Its foundations are in the colonial zone’s seldom- visited black neighbourhood of Santa Barbara. Another poignant sight is Plaza Colon’s bronze of Christopher Columbus “who appears powerful, gazing towards the horizon”.

A statue that says a thousand words, Taino Indian heroine Anacaona rests below him on the monument’s pedestal base. “She’s a wonderful woman in history that we should look up to more, but most people don’t even know who she is,” Ruth adds.

Take refuge from the broiling midday sun in the colonial zone’s Larimar Museum. Here, visitors can splurge on glittering jewellery fashioned from the brilliant blue Larimar gemstone that’s hand- mined from a single peak in the country’s Baoruco mountain range.

Satisfyingly, you don’t need to leave Santo Domingo’s limits to get your nature fix. After lunching on specialities like slow-cooked ‘seven meat’ sancocho stew or pollo guisado – braised chicken served with native vegetables such as auyama and malanga – head for the city’s beloved botanical gardens, a 20-minute taxi ride from Zona Colonial. `

An open-air sightseeing buggy is the best way to explore its sprawling 202 hectares, which are threaded by ornamental brick paths and freckled with more than 100 species of native orchid.

You can uncover more of the city’s natural wonders at Three Eyes National Park, which is thought to be a sacred ceremonial site once used by the country’s indigenous people. Discovered in 1916, this subterranean limestone cave system boasts a trio of turquoise lakes that the Taino refer to as eyes.

Mark your return to daylight with a sunset stroll along Santo Domingo’s popular seaside promenade, which runs roughly half the length of the city. If your itinerary allows, spend an evening being seduced by the lyrical rhythms of bachata at venues such as Lucia 203 or Jet Set Club. A genre of music fusing Cuban son and bolero with the country’s national dance, merengue, it was born in the Dominican Republic’s rural backwaters in the early 20th century.

GET ON BOARD
Windstar Cruises’ six-night The Spanish Main: Rise of the New World cruise aboard Star Pride, from San Juan (Puerto Rico) to Colon (Panama) via Santo Domingo (Dominican Republic), Cartagena (Colombia) and San Blas Islands (Panama), departs on December 7, 2025, from £2,252.

TUI’s seven-night Colours of the Caribbean cruise aboard Marella Explorer 2, return from La Romana (Dominican Republic) via Samana (Dominican Republic), Road Town (British Virgin Islands), Philipsburg (St Maarten), St John’s (Antigua) and Roseau (Dominica), departs on February 25, 2025. Fares from £1,781 including return flight from Birmingham.

PUERTO RICO
Formerly known as Boriquen, Puerto Rico was the first port of call for Spanish ships arriving in the Americas. One of the world’s oldest colonies, the archipelago owes its name – which translates as rich port – to the literal rivers of gold the Spaniards discovered here in 1508.

Those precious nuggets were fashioned into elaborate jewellery by Puerto Rico’s original hunter-gatherers, who were later enslaved and forced to pan for gold by the conquistadores. After failed conquests by the English, Dutch and French, the island eventually became a US territory following the Spanish- American War in 1898.

However, there are plenty of ways to connect with the island’s indigenous past, from kayaking along the petroglyph-studded Tanama River to eating at family-run chinchorros – rustic roadside kiosks – in Loiza on the east coast, near the capital of San Juan.

A two-hour scenic taxi ride into the central highlands delivers you to Utuado: one of a handful of Puerto Rican towns that has kept its native name. Spend a morning soaking in
the serenity of Utuado’s Caguana Indigenous Ceremonial Park, which turns the clock back
800 years.

Visitors stroll through a series of sun- dappled plazas known as bateyes – ceremonial ball courts used by the Taino – under crowns of sacred ceiba trees from which canoes were once carved.

There’s also an onsite botanical garden growing medicinal plants the Taino used, a pocket-sized museum displaying ancient artefacts, and 20 pre-Columbian petroglyphs etched with birds, human faces and divine figures.

Continue your exploration of the great outdoors in Puerto Rico’s northern karst region, recommended by Gabriel Lugo of Wildside Nature Tours as the best spot for bird-watching. “It hosts a rich variety of endemic and Caribbean species of birds in diverse habitats,” he says. “One good example of karst habitat is the Cambalache State Forest in the municipality of Arecibo.”

Biking and hiking trails snake through this 405-hectare swathe of jungle, punctuated with limestone pinnacles that reach 50m into the sky. “My favourite endemic bird is the Puerto Rican lizard cuckoo,” adds Gabriel.

“These large birds [nicknamed Big Ape Bird after their distinctive monkey-like ‘ka-ka-ka-ka’] call move along the branches quickly but with a precision that helps them catch their number one prey: lizards.”

GET ON BOARD
Silversea’s nine-night Fort Lauderdale (Florida) to Fort Lauderdale return cruise aboard Silver Moon, via San Juan (Puerto Rico), Gustavia (St Barthelemy), St John’s (Antigua), Basseterre (St Kitts and Nevis) and St Thomas (US Virgin Islands), departs on February 17, 2025. Fares from £5,600 including flights.

Royal Caribbean International’s seven-night Southern Caribbean cruise aboard Rhapsody of the Seas, return from San Juan (Puerto Rico) via St Croix (US Virgin Islands), Charlotte Amalie (St Thomas), Philipsburg (St Maarten), Fort de France (Martinique) and Bridgetown (Barbados). Departs on March 23, 2025. Fares from £609.