When it comes to holidays in the Caribbean, the common perception is that it’s all about beaches. But while it is true that the USP of many islands is palm-shaded sands lapped by a gin-clear bath-warm sea, the region offers so much more.
Choose the right destination and you can, for example, enjoy fantastic diving, snorkelling and sailing, trek through – and zip-line over – rainforests and visit fascinating sights associated with the islands’ complex colonial heritage.
In terms of accommodation, the region also offers a diverse range – not just large all-inclusive complexes but small-scale romantic hideaways, and not only high-end hotels but also excellent inexpensive guest houses.
This guide will help you find the ideal Caribbean holiday – whatever your taste, budget, or holiday style.
Best for couples…
The Caribbean is, of course, a prime destination for the romantically inclined. Within the region, however, the islands themselves and places to stay vary enormously, appealing to couples with differing priorities – whether that be a memorable beach, an adults-only environment, an escape-from-it-all hideaway, or perhaps great food.
The selection below covers some of the Caribbean’s best options for all these requirements, plus ideas for those who can’t sit long on a sun lounger.
In this section, unless otherwise stated, prices are per person for seven nights in November (low season), based on two sharing the cheapest accommodation, and including economy flights and transfers.
Show me the beach
1. Cap Juluca, Anguilla
In my opinion, the little British Overseas Territory of Anguilla has the best beaches of any Caribbean island. There are more than 30, most with the softest and whitest of sands lapped by a dazzling turquoise sea. One of the finest is the mile-long crescent of Maundays Bay.
It is home to the five-star hotel Cap Juluca, whose accommodation is spread over 15 domed and white Greco/Moorish-styled villas stretched along the rear of the beach, with the sand just beyond their terraces.
Book through Elegant Resorts, from £3,210 including breakfast.
2. Sugar Beach, A Viceroy Resort, St Lucia
Supremely elegant Sugar Beach has an extraordinary setting. It unfurls over a 100-acre estate between the cleavage of St Lucia’s pair of landmark Pitons, and within the scene is an arc of blinding white sand (imported from Guyana) – definitely the island’s most memorable strand.
If you tire of lounging on the sands or under the almond trees of the beachfront bar, the snorkelling and diving in the bay (a protected marine reserve) are excellent.
Booked through ITC Luxury Travel, from £2,449 room only.
3. La Sagesse, Grenada
For beach bums on a budget, I believe off-the-beaten-track La Sagesse is as good a base as anywhere in the Caribbean. It lies ensconced in palms directly behind a long, unspoiled and often virtually empty golden-sand beach at the rear of a scenic, horseshoe bay.
There are 12 plainly-furnished rooms, some in a pink manor house, others (more preferable) with terraces by the sand. Good local food is served in the simple, open-air restaurant behind the beach.
Booked through Just Grenada, from £1,085 room only.
4. Couples Swept Away, Jamaica
The large (300 plus rooms) but romantic Couples Swept Away is the domain of over 18s only, and lies in Negril, Jamaica’s most appealing resort. It spreads over mature tropical gardens that back on to a stretch of the fantastic Seven Mile Beach.
It’s a good option for active couples: the impressive sports facilities include a well-equipped gym, 25-metre lap pool and 10 floodlit tennis courts, and generous all-inclusive rates cover a host of watersports (including scuba diving) plus a catamaran cruise.
Booked through Virgin Holidays, from £1,769 all-inclusive.
5. Ti Kaye, St Lucia
Secluded, adults-only Ti Kaye ticks all the boxes for a romantic Caribbean getaway. Accommodation comes in the form of simply-furnished but quaint gingerbread cottages with open-air showers and to-die-for sea views from private terraces with hammocks, rocking chairs and in some cases plunge pools.
There’s a lovely, intimate cliff-edge spa, and steps descend to the gorgeous and often deserted silver sands of Anse Cochon. Good Creole food and excellent wines complete the picture.
Booked through Audley Travel, £1,694 including breakfast.
6. Little Arches, Barbados
If you’re looking for a small-scale, romantic and laid-back adults-only hotel, consider Little Arches. The hacienda-style property has just 10 individually designed bedrooms, some with plunge pools or outdoor whirlpool baths, and an excellent rooftop restaurant, Café Luna.
Local life is on the doorstep. The superb beach across the quiet lane in front of Little Arches is primarily used by Barbadians, and the hotel is on the outskirts of Oistins fishing village, famous for its Friday night fish fry street party.
Booked through Caribtours, from £1,349, including breakfast.
7. Petit St Vincent, St Vincent & The Grenadines
If you want to really get away from it all, a good bet is one of the private-island resorts in the Grenadines. These include Petit St Vincent, a 20-minute boat transfer from Union Island, whose 115 acres are fringed with pristine beaches.
The 22 secluded cottages and villas are without TVs, Wi-Fi or phones – you raise a flag for room service. Thrilling snorkelling and diving trips to the nearby Tobago Cays are on offer.
Booked through Carrier, £3,885 full board.
8. COMO Parrot Cay, Turks & Caicos
Much favoured by attention-avoiding celebrities, COMO Parrot Cay delivers privacy and romance in spades. It occupies a 1,000-acre private island – you arrive by boat on a 40-minute transfer from Providenciales.
Key attractions include a mile of pristine, white-sand beach perfect for arm-in-arm strolls, and the COMO Shambhala Retreat, a strong contender for the Caribbean’s best spa. The rooms, suites and villas have cool, minimalistic lines.
Booked through ITC Luxury Travel, from £1,713 including breakfast.
9. Sea-U Guest House, Barbados
You don’t need to spend a lot on a lovely hideaway in the Caribbean. Sea-U Guest House stands just back from the sea on Barbados’ palm-coated, unspoiled and little visited east coast, where Atlantic waves batter wild beaches (good for challenging surfing, not for safe swimming).
The laid-back property has 10 rustic-chic bedrooms, with planters’ chairs and hammocks on shared verandahs. Breakfasts, and sociable dinners available on some nights, are eaten in a gazebo in the pretty grounds.
Double rooms from around £109 per night, including breakfast.
For foodie heaven
10. Eden Rock, St Barths
The French outpost of St Barths is arguably the gourmet capital of the Caribbean, and the glamorous Eden Rock, on and alongside a rocky promontory on lively St Jean beach, is undoubtedly one of the best dining spots on the island.
Famous French chef Jean-Georges Vongerichten oversees the cuisine at the hotel’s two restaurants, the stylish and romantic On The Rocks, which offers exceptional seafood and desserts, and the more casual beachside Sand Bar.
Booked through Carrier, from £4,095 including breakfast.
11. Calabash, Grenada
Calabash, a tranquil, family-run luxury hotel set at the rear of a deep bay, offers easily the best food of any hotel in Grenada, and some of the most enjoyable I’ve eaten recently anywhere in the Caribbean.
Breakfasts are beautifully served on your terrace/balcony or the beach; lunches at the Beach Club revolve around memorable, gently spicy, tapas-sized dishes, while more formal dinners in Rhodes restaurant (as in Gary Rhodes, who provides guidance) include accomplished Caribbean/international fare.
Booked through Western & Oriental, £3,329 all-inclusive.
12. Boucan by Hotel Chocolat and Cap Maison, St Lucia
Start this two-centre break at Boucan by Hotel Chocolat. It lies on a cocoa-growing estate, and cocoa is included in virtually all the dishes (savoury and sweet), often with memorable results. Lessons are available to make your own chocolate bar.
Your second base is the elegant Spanish/Caribbean styled Cap Maison, whose clifftop Cliff at Cap is the stand-out restaurant in northern St Lucia, thanks to its excellent French/Caribbean cuisine and distant views out to Martinique; cooking classes with a market tour are offered.
Booked through Caribtours, four nights at Boucan by Hotel Chocolat, three nights at Cap Maison, from £1,925 including breakfast.
For active breaks
13. Small-ship cruise
Splash out on an upmarket small-ship cruise of the Caribbean, and not only will you get superior levels of comfort, food and service, but you can visit off-the-beaten-track harbours unable to accommodate bigger ships.
With Silversea, highly rated by Telegraph readers, options include Barbados-Barbados week-long itineraries taking in the delightful little Grenadines’ island of Bequia, as well as Grenada’s St George’s (one of the region’s prettiest ports) and Dutch Caribbean Aruba, Bonaire and Curaçao: for 8 December 2016 departure, from £2,949 all-inclusive.
14. Trinidad and Tobago
These sister islands offer the Caribbean’s richest and most diverse birdlife. Steppes Travel suggests four nights at Asa Wright Nature Centre, a world-famous birding lodge in Trinidad’s Northern Range, then four nights at Tobago’s Blue Waters Inn, which has birdwatching trails in the expansive grounds (and is also an ideal base for exploring Tobago’s excellent diving).
From £1,995, full board at Asa Wright, with breakfast at Blue Waters, and including several guided tours such as a boat trip of Trinidad’s Caroni Swamp to see scarlet ibis.
15. St Kitts and Nevis
St Kitts and Nevis combine perfectly for a two-island break: from one to the other takes just 10 minutes in a speedboat or 45 minutes by public ferry. The islands offer plenty to see and do, including impressive colonial sights such as St Kitts’ Brimstone Hill Fortress, remains of old sugar mills on Nevis, and rainforest hikes.
Booked through Western & Oriental, four nights room only at Ottley’s Plantation Inn, and three nights half board at beachfront Nisbet Plantation Beach Club, from £1,549.
16. Puerto Rico
Norwegian Airlines began flights from Gatwick to this Hispanic US commonwealth last winter, and this November it is restarting the twice-weekly service, with the flights operating through to March. With fares from under £300 return, the flights make Puerto Rico a possible budget Caribbean option; book car hire and hotels independently (seepuertorico.com is a good starting point).
Drive through the mountainous interior along La Ruta Panorámica, hike in El Yunque subtropical rainforest, and stop off in Ponce, an Art Nouveau gem.
Best for families
Many families heading to the Caribbean opt to hole up in a beachfront all-inclusive hotel with lots of facilities. There is nothing whatsoever wrong in doing that, but there are alternatives worth considering, including villas, apartments, cruises and even adventurous tours.
With children, it’s sensible to minimise flying time, so all the following suggestions can be reached on direct flights from the UK.
In this section, unless otherwise stated prices are lowest available for seven nights for a family of four sharing the cheapest suitable accommodation, including economy flights and transfers: with pre-school children in November (low season) with the children aged 2 and 4; with pre-teens and teenagers in the school summer holidays with the children aged 8 and 10, and 14 and 16 respectively.
With pre-school children
17. Carlisle Bay, Antigua
Carlisle Bay is a fairly rare breed in the Caribbean: a stylish, luxury hotel that is also genuinely child friendly. Families and couples stay at different ends of the property, in contemporary-styled suites overlooking the hotel’s lovely beach and a deep, verdant bay.
The highly-rated Cool Kids Club, for children six months to six years (free for over twos, $15 an hour for younger ones) has its own paddling pool; dining options include pizzas and home-made ice-cream; and the glam cinema shows family films.
Booked through Elegant Resorts, from £9,750 including breakfast.
18. Beaches Negril, Jamaica
Beaches, the family-oriented sister brand to Sandals, has three fun, activity-filled all-inclusive properties in the Caribbean, one on Turks & Caicos, two on Jamaica. Sesame Street characters make appearances, and unusually for Caribbean hotels, nurseries/children’s clubs supervised by certified nannies are available for babies and toddlers and included in the rates.
Beaches Negril, the smallest (186 rooms) of the hotels, is set on Negril’s superb, miles-long sandy beach, and has a pirate-themed waterpark with slides and water cannon.
Booked through Virgin Holidays, from £5,695 all-inclusive.
19. Lance aux Epines Cottages, Grenada
Lance aux Epines Cottages is a good few-frills, self-catering option. Its 11 cottages and apartments would win no design prizes. But they are roomy, homely and well-equipped, and spread over three acres of attractive, lawned gardens that back on to a peaceful and protected sandy beach at the rear of yacht-filled Prickly Bay where the water is ideal for paddling and safe swimming. (Note there is no pool).
Babysitting and the services of a cook are available at low rates.
Booked through Just Grenada, from £3,595.
20. Caribbean cruise
I’ve taken a cruise with my family in the region, and can testify that such trips are ideal with children. For one thing, they are light on sightseeing – time ashore can be spent on the beach, snorkelling or zip-wiring through a rainforest canopy.
We travelled with Carnival (large, lively ships with mostly an American clientele) from Barbados on a busy Southern Caribbean cruise, stopping at St Lucia, St Kitts, St Maarten, San Juan and St Thomas.
Booked through Virgin Holidays Cruises, in August 2017 seven nights full board on Carnival Fascination plus a night all-inclusive at a Barbados hotel, from £6,596.
21. Atlantis Paradise Island, Bahamas
Over-the-top, 3,600-room Atlantis Paradise Island is not for the faint-hearted. But with its vast water park with near-vertical slide down a faux Mayan temple, a mile of river rides and 11 pools, plus a giant aquarium and activities such as swimming with dolphins, the children certainly won’t be bored. In the evenings, 9-13 year olds have their own club for video gaming, karaoke and dancing.
Booked through Kuoni, from £6,179 room only in a Beach Towers Terrace Room.
22. Dreams Palm Beach, Dominican Republic
A big all-inclusive hotel in the Dom Rep is a sensible choice for taking the family to the Caribbean without breaking the bank. One of the best mid- to upper-range family-friendly hotels is Dreams Palm Beach Punta Cana.
It backs on to a palm-dotted beach with reef-protected waters, and offers good food (for a 500-room all-inclusive), with unlimited access to à la carte dining options. Children’s club activities include movies on the sand after dark.
Booked through Kuoni, from £5,176 all-inclusive.
23. A villa in Barbados
Renting a Caribbean villa can be surprisingly affordable in the low-season summer months (though airfares then are relatively high). Barbados has one of the biggest selection of villas.
An ideal location is right on a beach on the upmarket west coast – you could then skip having a pool as the sea on this side of the island is usually mill-pond calm. Fitting this description is three-bedroom Aquamarine, right by Mullins Beach.
Booked through CV Villas, a week’s rental only in July/August £2,276, including flights and car hire £6,105.
24. Beach View, Barbados
I’ve stayed with my boys at Beach View and highly recommend it as a reasonably-priced, family-friendly west-coast base. It’s a smart, family-run complex of 36 apartments overlooking an enticing pool area, with vast adult and children’s pools.
The apartments are spacious and have well-equipped kitchens, plus other useful facilities such as washing machines. You have to cross a busy coastal road to get to Paynes Bay beach, but it’s one of the finest strands on the island.
Booked through Virgin Holidays, from £4,815 room only.
25. Nonsuch Bay, Antigua
On a reef-protected bay in eastern Antigua, Nonsuch Bay is a great choice for yachty families, or those wanting to learn the ropes. It has a fleet of sailing craft and a sailing school with instruction for all ages and abilities. Accommodation includes spacious and well-equipped suites and cottages that work well for families.
Booked through Carrier, £5,850 all-inclusive in a two-bedroom Deluxe Suite, with group sailing tuition and independent use of sailboats. Kitesurfing, windsurfing and stand-up paddleboarding are also available, but cost extra.
26. Jakes, Jamaica
It’s a long (2½ hours) transfer from Montego Bay to Jakes at Treasure Beach, a fishing and farming community on Jamaica’s south coast. But teenagers should love this rustic-chic property, with its informal vibe and funky look – you stay in cottages quirkily decorated with shells, coloured glass and mosaic tiles.
Dining options include jerk pizzas at Jack Sprat, and among the excursions on offer are boat trips to Pelican Bar, perched on a sandbar out to sea.
Booked through Steppes Travel, over February half term £5,800 room only in a two-bedroom cottage.
27. Bay Gardens Beach Resort, St Lucia
Colourful Bay Gardens Beach Resort is right on long and busy Reduit Beach, and offers watersports galore (non-motorised ones for free) and Splash Island Water Park, a vast, inflatable obstacle course in the sea that opened last summer.
Teenagers will also like the fact that the hotel is in easy walking distance of lively Rodney Bay resort’s many bars, cafés and restaurants.
Booked through Best at Travel, £5,730 in a One Bedroom Pool View Suite, including breakfast, a US$150 (around £115) food and drink credit, and six Splash Island passes.
28. Cuba tour
Not everything works smoothly in Cuba, the food isn’t great, and journeys can be long if touring. So for an exploratory family holiday, it’s better suited to older children. With ubiquitous live music, old Cadillacs, iconic heroes like Che Guevara and quirky communist ways, teenagers should find the country culturally fascinating.
Explore runs 15-day small-group Cuba family adventure holidays, encompassing historical sights, activities in the mountains and beaches, with some departures for children 11 or older: adults from £2,380, children from £2,230, including some meals and flights.
Best for solo travellers
Though the Caribbean isn’t the most obvious part of the world to head to on your own, St Lucia’s The BodyHoliday is very focused on single guests, and a high proportion of those on exploratory group tours of Cuba and other islands are solo travellers.
In this section, unless otherwise stated, prices are for seven nights in November (low season) in the cheapest suitable accommodation, including any single supplements, economy flights and transfers.
For a sociable trip
29. The BodyHoliday, St Lucia
At The BodyHoliday, an upmarket wellness/fitness-oriented hotel, an impressive amount is covered in the all-inclusive rates, including a daily treatment in its large Moorish spa complex, yoga, Pilates and tai chi sessions, and lots of sports (even waterskiing and some diving).
With appealing single bedrooms and communal dining on offer, stays here are understandably very popular with solo travellers.
Booked through Wellbeing Escapes, from £2,599 all-inclusive, with US$250 (around £190) credit for additional spa treatments and private sports lessons.
30. Bequia, St Vincent & The Grenadines
Easy-going and unhassly Bequia has a friendly ex-pat community and in the winter months is visited by lots of gregarious yachties – Port Elizabeth, the villagey capital, overlooks Admiralty Bay, one of the Caribbean’s prettiest natural harbours.
The bars and restaurants along the waterfront Belmont Walkway, such as the atmospheric Frangipani, are the island’s social focal point. Stay next door to the Frangi at the charming Gingerbread Hotel; visitors drop in to its café and garden for home-made cakes and ice-creams.
Booked through Just Bequia, from £1,825 room only.
31. Homestay, Havana, Cuba
Cuba is one of the most sociable places to visit on the planet: it’s hard to walk down a street in Havana without someone trying to befriend you. To really mingle with the locals – and minimise costs – stay in a casa particular (private home).
There are hundreds to choose from in Havana on Airbnb, many in faded colonial mansions with multiple, positive reviews from previous guests; for a private room, average rates are just £31 a night.
32. Scuba diving, Cayman Islands
Diving is a great bonding activity for singles. Arguably the best place to do it in the Caribbean – for any level of ability – is the Cayman Islands, and the waters off sleepy Little Cayman, which include the world-famous Bloody Bay Wall vertical drop, are particularly special.
Booked through Original Diving, from £4,000 full board in a beachfront bungalow at the casually sophisticated Southern Cross Club on Little Cayman, including six mornings of two-tank dives with the hotel’s own dive operation.
33. Walking holiday, Dominica
Mountainous, coated in dense rainforest and home to impressive waterfalls and rare parrots, Dominica is the Caribbean’s nature isle par excellence. And it is a walker’s paradise.
KE Adventure Travel runs guided, small-group trekking holidays to the island, with luggage transported between small hotels and guesthouses and four or five hours’ walking most days on forest trails and coastal paths. One day there’s the option for a longer hike through the steaming Valley of Desolation to the Boiling Lake (a flooded volcanic fumerole).
Ten days in May from £3,195 full board, sharing rooms with person of the same sex.
34. Music tour, Cuba
Intrepid Travel’s eight-night escorted Cuba, Music & Dance tours sound like great ice-breakers, so unsurprisingly lots of singles sign up.
Visiting Havana, the gorgeous colonial town of Trinidad and the country’s second city of Santiago de Cuba, the trips encompass everything from son and salsa to ballet, and include dance lessons, a percussion workshop and visits to renowned live music venues. You stay with local families.
Departing mid-October, from £896 sharing rooms with person of the same sex, breakfasts and some activities, but excluding transatlantic flights; single supplement for private rooms £330.
Best for groups
The Caribbean has good options for group holidays, including large, staffed standalone villas that are perfect for house parties with friends, and villas and apartments within hotels that are ideal for a multi-generational family of children, parents and grandparents.
In this section, unless otherwise stated, prices are for seven nights, including economy flights and transfers: for holidays with friends, per person in November (low season); for multi-generational holidays the total cost for a group of six (four adults; two children aged 8 and 10) travelling in the school summer holidays.
35. Large villa rental, Jamaica
The cost per person of renting a sizeable Caribbean villa can work out very reasonably if you fill all the bedrooms. For example, CV Villas offers Keela Wee, an attractive-looking villa sleeping 12 near Ocho Rios on Jamaica complete with its own sandy cove, large pool and tennis court, and the services of a cook for three meals a day included in the rates (though not the food).
Based on 12 sharing, £1,598 a head for a week’s rental, including flights and car hire.
36. Sailing, British Virgin Islands
How about a holiday on a yacht with a group of friends? The British Virgin Islands is ideal territory – especially for novices, given the short hops between the archipelago’s many green blobs of land and the line-of-sight navigation.
Sunsail offers flotilla holidays (sailing in a group of yachts with lead crew support) and bareboat charters in the BVI.
For a week’s flotilla sailing on a 46ft yacht sleeping six in three cabins, from £1,299 per person based on six sharing, including flights and transfers.
37. Cycle tour, Cuba
For a sweaty adventure, get a bunch of friends to sign up for a group bike holiday in Cuba. With Saddle Skadaddle, options on the Caribbean’s largest island include Cuban Wheels, a week of gentle/moderate cycling (up to 45 miles a day) between the atmospheric towns of Santa Clara, Sancti Spiritus, Trinidad and Cienfuegos in central Cuba, with time for sightseeing and the beach.
In March, from £1,395 per person staying in hotels and a private home with breakfast and most lunches, but excluding bike hire (£150) and flights.
For multi-generational groups
38. Little Good Harbour, Barbados
With good sightseeing (plantation houses, lovely gardens), activities ranging from golf to swimming with turtles, great restaurants and good beaches, Barbados works well for visitors of all ages and proclivities.
Off-the-beaten-track Little Good Harbour, in a fishing community on the north-west coast, is very popular with families, as you stay in cottage-like suites with kitchens and indoor/outdoor living areas; the three-bedroom Vineyard Suites are particularly spacious and stylish. Added attractions include two swimming pools and The Fish Pot, an excellent, casual-chic beachfront restaurant. Plan on renting a car.
Booked through Turquoise Holidays, £8,199 room only in a Vineyard Suite, including car hire.
39 Windjammer Landing, St Lucia
Windjammer Landing is a prime example of a “villa hotel”. Most of its accommodation comprises suites or villas with kitchens, sitting rooms and sometimes private pools, while you also have the trappings of a large hotel, such as restaurants, watersports, tennis courts, spa and children’s club.
All of which makes the Mediterranean-looking complex ideal for a multi-generational group with differing needs, though less mobile oldies should note that some accommodation lies up a steep hillside.
Booked through Trailfinders, £7,399 room only in a two-bedroom villa.
40. True Blue Bay, Grenada
At the rear of a yacht-filled bay, jovial and colourful True Blue Bay is another multifaceted property well suited to a multi-generational family – particularly if staying in one of its five swanky big two-bedroom villas with private plunge pools.
On-site facilities include the Dodgy Dock, a lively and informal bar/restaurant on a deck over the water, two appealing swimming pools, a well-regarded dive centre, kayaks and Hobie Cats. Spectacular Grand Anse beach is a free shuttle ride away.
Booked through Caribtours, £6,235 including breakfast in a two-bedroom villa.