The Caribbean – but not as you know it

·17-min read
caribbean islands travel holidays winter sun journeys family holidays adventure
caribbean islands travel holidays winter sun journeys family holidays adventure

There is a solid school of thought that says you shouldn’t mess with perfection. It is widely accepted that a Leonardo painting needs no reimagining by modern hands; that Mozart’s Requiem does not require a dance remix. If the dogs stretched out by the roaring fire are of flawless pedigree, then let them sleep.

You might apply all of the above to the Caribbean beach holiday. With the exception of this month and next – when Atlantic hurricane season is at its most potentially troublesome – there is nothing to sully the concept of a getaway to this realm of scattered islands and blue skies. The Caribbean is sun-and-sea escapism in its purest form, all soft sands and warm shallows. Once you have checked into your resort by the waves, why would you want to leave it (particularly when there are cocktails to be sipped and sunsets to be admired)?

It is an entirely reasonable argument. Yet it is one that misses a broader point. While the Caribbean is undoubtedly home to some of the planet’s loveliest beaches (few on St Lucia, Antigua, Grenada, Jamaica and myriad other islands would dispute this claim), there is also a great deal to enjoy beyond the shoreline.

Mountainous and majestic in its higher places, with an added element of volcanic spice on those summits where the Earth cracks open, here is a region thrillingly suited to adventurous breaks; to hikes on winding paths and cycling tours along country roads. Its (rain)forests reverberate with the songs and serenades of rare birds; its ports, towns and cities murmur in memory of eras past. Yes, by all means, you can snooze on your sun-lounger. But there is more. So much more.

caribbean islands travel holidays winter sun - Peter Frank Edwards/Redux
caribbean islands travel holidays winter sun - Peter Frank Edwards/Redux

With the prime time for visiting the region approaching (November is generally seen as the curtain-raising month) we have picked out a raft of options for those who want to enjoy the Caribbean beyond the – admittedly wonderful – obvious. We’ve focused on the Caribbean islands; the coastlines of Colombia, Mexico, Costa Rica et al will keep for another day. But from the streets of Santiago de Cuba to the trails of Dominica, below are 20 holiday options that offer something different.

Nobody is trying to argue with travel perfection; we are simply acknowledging that there is an alternative.

Firm footsteps on Barbados

Were you to summon the classic image of Caribbean holiday-making indolence, you might find yourself looking at a picture of Barbados’s west coast, and the sophisticated resorts which bejewel it. But while the region’s easternmost island doesn’t deal in the sort of mighty altitude provided by some of its colleagues (its peak is the 1,120ft Mount Hillaby), it has enough distant places and rugged corners to make for gently active breaks. Not least along an east coast, facing the open Atlantic, vastly different to the west.

How to do it

Ramblers Walking Holidays (01707 819180; ramblersholidays.co.uk) is offering an 11-day Beautiful Barbados escorted tour which visits much of the island, including Farley Hill National Park with its widescreen views, and North Point at the upper tip of the landmass. The next departure is on November 11 – from £2,695 per person (including flights).

Feathers aflutter in the Dom Rep

The Dominican Republic has earned something of a reputation as a reliable option for a beach break, drawing tourists to the increasingly luxurious resorts around the south-easterly Punta Cana. But as the bigger brother of the second largest Caribbean island – it shares Hispaniola with Haiti – it can also be wild, craggy and untamed. Its protected spaces include Los Haitises National Park, a dense area of mangrove forest only really accessible by boat, and Jaragua National Park, nearly on the Haitian border, with its population of flamingos.

How to do it

Responsible Travel (01273 823700; responsibletravel.com) offers a five-day Dominican Republic Wildlife Tour which calls upon Jaragua – and on Sierra de Bahoruco National Park, for cuckoos and amazons. From £1,995 per person (flights extra).

Marine mammals at Silver Bank

The wildlife show continues in the waters off the Dominican Republic. The country claims ownership of Silver Bank, a 650-square-mile patch of sedimentary stone and coral which spreads out just below the surface some 80 miles off the north coast of the country, declaring it a “Sanctuary for Marine Mammals”. It is an appropriate description. The area is a prime breeding and calving zone for humpback whales, particularly between January and April.

How to do it

Dive Worldwide (01962 302087; diveworldwide.com) is offering group holidays to the area during this four-month window. Six of the 11 days are spent on a “liveaboard” boat at Silver Bank, snorkelling with these huge animals. From £4,995 per person (including flights).

dominican republic wildlife - Getty
dominican republic wildlife - Getty

Family fun beyond Havana

Such is the size (42,426 square miles) of the Caribbean’s largest island that to treat it as a mere beach destination is to miss the point. True, Cuba has some gorgeous arcs of sand, and modern resort accommodation galore (notably at Varadero), but it is much more than a week by the sea. While many of its attributes are well known – the faded grandeur of Havana, endless echoes of revolution – much of this big country is a mystery to travellers.

How to do it

Journey Latin America (020 3733 0729; journeylatinamerica.com) lifts the lid for tourists of all ages with Family Cuba: Salsa, Beach and Vintage Cars. This 15-day trip tours the capital in a classic car – and does head to the beach, off the north coast, on the islet of Cayo Santa Maria – but also enjoys a salsa lesson in Trinidad, and ventures into the Zapata wetlands for encounters with crocodiles. From £3,076 per person (including flights).

Rolling with it across Cuba

Cuba’s epic scale and relative lack of motorised traffic makes it a splendid choice for a cycling holiday. This can mean time in the south-east, which is a different beast to the north-west and Havana, where the Sierra Maestra (a hotbed of revolution in the 1950s) rises, and the vibrant second city Santiago de Cuba (550 miles from the capital) never appears to sleep.

How to do it: Saddle Skedaddle (01912 651 110; skedaddle.com) offers a Cuban Revolutions tour which explores the island at a semi-unhurried pace, covering 300 miles in 15 days and rolling through Pinar del Rio province, as well as Havana and the south-east; next edition Jan 28. From £3,355 per person (flights and bike hire extra).

Santiago de Cuba travel holidays - robertharding.com
Santiago de Cuba travel holidays - robertharding.com

Best feet forward on tiny Dominica

In contrast to some of the titans of the region, Dominica is a pin-head in the ocean, its 290 square miles making it just 1.5 per cent the size of its near-namesake on Hispaniola. But what it lacks in heft, it offers in beauty. Its tagline, “Nature Island of the Caribbean”, is no misdirection, playing out in volcanic contours, thermal springs and a thick blanket of rainforest. It is a special gift to hikers in its 115-mile Waitukubuli Trail, which crosses the island, from the south-coast village Scott’s Head to Cabrits National Park in the north.

How to do it

World Expeditions (0800 074 4135; worldexpeditions.com) has a pair of 11-day group excursions along what is the longest hiking trail in the Caribbean scheduled for this winter (Nov 20-30; Dec 18-28), from £3,200 per person (flights not included).

Parrots and past tense on Puerto Rico

In theory, Puerto Rico should hold considerable appeal for UK tourists. Not only is it the fourth largest island in the Caribbean, it is also American (or, at least, a “US Territory”). In reality, a lack of easy accessibility – there are no direct flights from Britain – renders it something of an unknown quantity for travellers from these shores. The flip-side to this, of course, is that there is much to discover for those who do make the jump – including the 17th-century throwback of Old San Juan, and the calmness of satellite island Vieques.

How to do it

Naturetrek (01962 733051; naturetrek.co.uk) goes deep into the woods with The Birds of Puerto Rico – a nine-day group tour that goes in search of parrots and warblers in Rio Abajo State Forest and El Yunque National Forest, but also absorbs the historic atmosphere in the capital. Next departure March 7, from £3,495 per person (with flights).

puerto rico holidays tours - Shutterstock
puerto rico holidays tours - Shutterstock

Beaks and peaks on Trinidad

Trinidad also falls into the “big but unknown” category when it comes to tourism in the Caribbean; the region’s fifth biggest island rarely features highly on lists of obvious sunshine destinations. Perhaps this is because it lies so close to South America – you can see Venezuela from its westerly Chaguaramas Peninsula – that it seems part of another continent. Or perhaps it is because, forested and rugged in large parts of its landmass, it does not feel like a travel option which looks to the beach. Wildlife, on the other hand …

How to do it

Wildlife Worldwide (01962 302086; wildlifeworldwide.com) is offering A Carnival of Wildlife: a 10-day holiday that searches for the scarlet ibis in the Caroni Swamp on the west coast, and uses the Asa Wright Nature Centre as a base for spotting oilbirds and collared trogons in the Northern Range. From £3,995 per person (with flights).

Twice as spice on a twin-island holiday

Grenada’s status as the Caribbean’s most fabled “Spice Island” – cinnamon, cloves and turmeric are also important crops – makes it ideal terrain for a break with a foodie theme.

How to do it

Scott Dunn (020 3733 0854; scottdunn.com) serves up a 10-day Culinary Caribbean getaway which splits its time between Grenada and St Lucia. On the former, it’s a five-night stay at the Calabash Hotel (calabashhotel.com) – a boutique retreat on the south coast where the signature restaurant still runs to the recipes of the late Gary Rhodes. On the latter island, it’s a six-day stay at the Rabot Hotel, the former Hotel Chocolat (hotelchocolat.com/uk/rabothotel); an accommodation jewel which, in spite of the name change, still sits on a rainforest-wrapped cocoa estate (and offers chocolate-related spa and dining experiences to match). From £3,600 per person (including flights).

Hotel Chocolat Saint Lucia holidays travel - Peter Frank Edwards/Redux
Hotel Chocolat Saint Lucia holidays travel - Peter Frank Edwards/Redux

French inflections on Guadeloupe

Partly guided by history, partly by direct flight routes, the British view of the Caribbean tends to focus on established favourites – Barbados, Antigua et al. But many parts of the region come with a French accent – and, for many travellers from the UK, an air of unfamiliarity. This is the case with Guadeloupe, one of France’s “overseas departments” in the region. Whether you regard it as one island or two – technically, it exists as two halves, Grande-Terre and Basse-Terre – it is a place that bears exploration. Visitors should certainly forge out to the slopes of La Grande Soufriere, the 4,813ft volcano that shapes both Basse-Terre and Guadeloupe National Park (guadeloupe-parcnational.fr).

How to do it

The Inspiring Travel Company (01244 729848; inspiringtravel.co.uk) offers a seven-night Discover Guadeloupe package from £1,926 per person (including flights).

Coral and curiosity on the Caymans

Cut adrift west of Jamaica, south of Cuba, the Cayman Islands are also rarely acclaimed as a context for island-hopping (or indeed, as an obvious choice for sun-and-sand holidays, if the broader view of them as dry hubs of off-shore finance is taken into account). And yet, with just three members to its little club – Grand Cayman, Little Cayman and Cayman Brac – this is an archipelago that can be seen in full in just over a week.

How to do it

Black Tomato (020 3026 7286; blacktomato.com) offers See it all in the Cayman Islands – a 10-day game of hopscotch that showcases the three islands with an emphasis on activity. Grand Cayman means diving at the coral temple of the North Wall, or amid the swirl of Stingray City. Little Cayman makes for fishing in Bloody Bay Marine Park. Cayman Brac serves up caves, cliffs and hiking trails. From £5,000 per person (flights extra).

Scuba diving Grand Cayman
Scuba diving Grand Cayman

Green fingers on Grenada

Providing a southerly full-stop to the Grenadines island chain, Grenada can be an alternative choice for a beach holiday – perhaps at one of the deluxe resorts which adorn the likes of Morne Rouge Beach and Grand Anse Beach at its south-western tip. But it can also be the setting for a holiday which peers inland, rather than at sparkling shallows.

How to do it

Brightwater Holidays (01334 657155; brightwaterholidays.com) runs a nine-day Gardens of the Spice Island group holiday which focuses on Grenada’s cultivated spaces. These include Smithy’s Garden, which tries to bring order to rainforest wildness across two sloping acres, and the Balthazar Estate, with its rich harvests of nutmeg and ginger. The next departure is planned for May 13 – from £2,695 per person (with flights).

Marley and me on Jamaica

Tucked into the water 90 miles due south of Cuba, Jamaica is another of the Caribbean giants. The holidaymaker’s perspective on it is often limited to the high-end beach hotels along the north coast – including at Montego Bay and Ocho Rios. But the scope of what is the region’s third largest island also makes for extended itineraries and wider wanderings.

How to do it

Explore (01252 883761; explore.co.uk) offers an Explore Jamaica group break; a wide-ranging 10-day affair which delves into Bob Marley’s legacy at his former home in Kingston, hits the heights and coffee plantations of Blue Mountains National Park, and ventures to both ends of the island – Port Antonio in the east; Negril and Seven Mile Beach in the west. Next departure Oct 31, from £2,861 per person (including flights).

bob marley travel holidays - Jean Bernard Sohiez
bob marley travel holidays - Jean Bernard Sohiez

Body consciousness on St Lucia

Famously, St Lucia has some of the Caribbean’s most photogenic beaches – Anse Cochon, midway up its west coast; and the venerated Anse Chastanet, caught in the shadow of the totemic Pitons, a little further to the south. But while the shoreline will always issue a siren call to travellers, it doesn’t need to be the sole focus – even at a luxury resort.

How to do it

Set at the north tip of the island, the Body Holiday resort (thebodyholiday.com) – as it name suggests – encourages its guests to focus on their wellbeing, via spa treatments, fitness programmes and watersports. A seven-night all-inclusive stay costs from £1,660 per person (flights extra) via Wellbeing Escapes (020 3735 7555; wellbeingescapes.com).

Gone with the wind in the Grenadines

With the friendly tides of its west coast – where the Caribbean Sea, rather than the open Atlantic, comes to shore – St Lucia can be an excellent base for a watersports holiday. But it can also be the start-point for a longer adventure that flirts with the wind and currents…

How to do it

Planet Windsurf (01273 921001; planetwindsurfholidays.com) offers a two-week Sailing and Stay in St Lucia and the Grenadines holiday – from £3,050 per person, including flights. This divides its time between the Coconut Bay Resort at the south tip of St Lucia and a small-ship voyage down through the Grenadines for kite-surfing escapades in the waters off the various isles; St Vincent, Bequia, Canouan, Mayreau et al.

the grenadines travel holidays
the grenadines travel holidays

Tee time on Canouan

Though technically one nation, the long, curving necklace of St Vincent and the Grenadines is a place of differing characteristics and qualities. Some of the islands (such as Mustique) are chic and elegant; others are rocky and uninhabited (Battowia is largely a bird sanctuary). Somewhere in the middle sits Canouan, a nugget of just three square miles and 1,700 souls, which stands as a glorious, niche option for a week on the fairway.

How to do it

Your Golf Travel (0800 043 6644; yourgolftravel.com) offers breaks to the Canouan Estate – a five-star enclave with a testing 18-hole championship course laid out along the shore. A one-week stay costs from £4,225 per person (including flights and three rounds).

Buccaneering around the Bahamas

One of the joys of eschewing a single island for a Caribbean archipelago is that you can leap around its constituent parts – even if that archipelago is best known for breaks where you find a resort and a lounger, and stay put. This might certainly be the case with the Bahamas; a popular choice for lazy stays – but also an option for island-hopping.

How to do it

Bon Voyage (0800 316 3012; bon-voyage.co.uk) offers a 12-day tour of the country which begins on New Providence – where the 18th-century Fort Montagu still “guards” the capital Nassau, and Blackbeard’s ghost (probably) haunts the former base-island of the “Republic of Pirates”. Further stops include Great and Little Exuma for snorkelling and seafood, and Eleuthera for kayaks and turtles. From £3,459 per person (with flights).

Bahamas Island Hopping - The Bahamas Ministry of Tourism and Aviation
Bahamas Island Hopping - The Bahamas Ministry of Tourism and Aviation

All at sea in the BVIs

Clustered more closely than the Caymans, the British Virgin Islands are another good idea for holidaymakers who want more than a single place in the sun. This “overseas territory” is a cornucopia of Caribbean life, its four main outcrops – Tortola, Anegada, Virgin Gorda and Jost Van Dyke – supplemented by 50 other islets and cays. Road Town – the capital, on Tortola – has an inevitable pretty charm. Mount Sage National Park, near the western end of the same island, ring-fences 1,716ft of volcanic magnificence.

How to do it

Abercrombie & Kent (0330 173 4712; abercrombiekent.co.uk) is offering a stylish way to tour the BVIs – six-berth yacht the Moorings. A seven-night charter costs from £5,999 per person (based on six sharing – including flights, and a dedicated captain and chef).

Living life on the Leeward side

The simplest method of Caribbean island-hopping is, of course, via a cabin and a cruise… On December 4, small-ship specialist Seadream Yacht Club (00 47 6779 2585; seadream.com) will launch a six-day Leeward Islands Explorer cruise that will slip into a range of exotic harbours along the line where the Caribbean Sea and the Atlantic meet. The BVIs and Puerto Rico (the end of the voyage) will be part of the itinerary, as will the French-Dutch island of St Martin (the start-point), ever-refined St Barts, and Nevis. The latter, the junior partner to bigger St Kitts, may prove the highlight – its central peak towering up in visibly volcanic fashion. From £3,170 per person (flights extra)

Windward ho with a fortnight on deck

If glimpsing “just” the Leeward Islands on a Caribbean cruise feels like an abridged endeavour, what of a more detailed voyage which calls on the Windward Islands as well? Silversea (0844 251 0837; silversea.com) offers a Bridgetown to Bridgetown cruise scheduled for Nov 24-Dec 5. As its title suggests, this 11-day voyage will start and end in Barbados. It will also go south, to Bequia and Grenada, as well as north-west to the Virgin Islands (both US and British) and Puerto Rico. Other stops will be Antigua, lava-engulfed Montserrat (where major eruptions in 1995 and 2010 buried half the island), and French connection Martinique. From £5,300 per person (including flights)

Covid rules

For full details of entry requirements and Covid rules for your favourite destinations, see telegraph.co.uk/tt-travelrules. Refer to gov.uk/foreign-travel-advice for further travel information.

Have you visited any of these places in the Caribbean? Please share your experiences and tips in the comments below