The best Caribbean twin-centre holidays

Why settle for one island when you can have two? Our experts have paired up the Caribbean's most irresistible stays to help you find your perfect match.

Best for beaches of dreams: Turks & Caicos

With beaches that rival the Maldives and water dubbed the ‘rainforest of the sea’, Turks & Caicos proves the Caribbean still has a few secrets worth keeping. Start in Providenciales (Provo) at Wymara Resort & Villas, a sleek seaside stay that earns its title as one of the Leading Hotels of the World. Step from the terrace straight onto Grace Bay’s powdery sand or stretch out by the mirror-smooth pool with a fruity cocktail from the Pink Bar.

To see Turks & Caicos at its wildest, you’ll then head south to Salterra Resort & Spa on South Caicos, where beach meets nature in spectacular form. Here, salt flats fade into flamingo-pink horizons and coral reefs fringe the white-gold coast. Sustainability isn’t a slogan but a way of life, from reef-restoration projects to spa rituals inspired by the island’s botanicals; don’t miss the cleansing salt ritual, infused with the aromas of lemongrass and lavender.

Best for flavour and flair: St Lucia & Grenada

This is a Caribbean double act with all the right ingredients – beaches, rainforest and seriously good chocolate. Begin in St Lucia at Windjammer Landing Resort & Residences, where terracotta roofs peek through palms and villas spill down to a curve of clear, blue-green water. Take a catamaran around the Pitons, follow reef walls fizzing with volcanic vents or zipline through the rainforest before sundowners on the deck. For a sweet finale, add on a few nights stay at Rabot Hotel by Hotel Chocolate.

After a few lively days, fly south to Grenada and settle into Calabash Grenada, a family-run hotel that’s been welcoming guests since the 1980s. The team’s passion for the island shows in every detail; we love the daily complimentary touches included in your stay, from canapés in your suite to dainty afternoon tea. Away from the sanctuary of the resort, tour a rum distillery, learn the art of cacao-making on a local estate or stroll the sugar-soft sweep of Grand Anse Beach – often voted among the world’s best.

Best for a mid-holiday glow-up: Antigua Access All Areas

Antigua might be small, but it packs in more beaches than there are days in the year — and no two stays here feel the same. Begin at Pineapple Beach Club, where mornings start with salt on your skin and the smell of barbecued snapper drifting from the grill. Paddleboard in the shallows, join a rum-tasting by the beach bar and watch the sky blush pink over Long Bay.

Next, dial up the luxe at Galley Bay Resort & Spa, a barefoot-luxury hideaway tucked behind tropical gardens and a curve of white sand. Dining here is a standout: graze on Caribbean flavours at Sea Grape, slip off your sandals for a candlelit tasting menu at Ismay’s or dine under thatched cabanas at Gauguin with the waves just a few steps away. When you’re ready to roam, wander St John’s for spice stalls and steel-band rhythm or take a catamaran around the island to count those famous beaches for yourself.

Best for a classic-meets-castaway contrast: Barbados & the Grenadines

Barbados is the Caribbean icon that never goes out of style. Check into Sea Breeze Beach House by Ocean Hotels, a boho-chic hideaway brushing the sands of Maxwell Beach. Spend your days sailing over turquoise water, practising your swing on the nearby golf course and sampling small-batch rums before dinner. Evenings are for sea-breeze suppers or wandering into the heart of the action – you’re only a five-minute stroll from lively St Lawrence Gap.

After the glitz and glam of Barbados, slow the tempo in the sleepy Grenadines at Bequia Beach Hotel, a retro-glam resort on beautiful Friendship Bay, where island life feels wonderfully unvarnished. You’ll spot fishermen hauling in their catch, locals chatting over crates of mangoes on the dock and reef boats bound for sites that put the Grenadines on every diver’s map. After dark, dine toes-in-sand at Bagatelle before heading to Jack’s Beach Bar, where the rum punch flows and the sunsets are spellbinding.

Best for culture and coast: Jamaica two-stop trip

There’s nowhere with a sense of place quite like Jamaica – bold, bright and brimming with character. Begin in Kingston at the sleek S Hotel Kingston, where murals of reggae legends and rooftop cocktails set the scene for the island’s creative heartbeat. Explore the capital’s food markets and galleries or head into the Blue Mountains for a taste of Jamaica’s famous brew.

Down on the coast, S Hotel Montego Bay picks up the Kingston beat and gives it a sun-soaked remix. The whitewashed façade backs straight onto Doctor’s Cave Beach, one of the island’s most celebrated stretches of sand. Inside, you'll find polished wood, woven textures and pops of Jamaican art, while outside, the energy of Mo’Bay hums along the Hip Strip. Between dips in the glass-sided rooftop pool, lazy book reads on a cherry red day bed and spa rituals laced with sugar cane and coconut, it’s easy to see why this is one of our go-to spots for a hit of Jamaican style and soul.

Best for together time in style: Antigua & St Kitts

Start your Caribbean escape in Antigua, where Carlisle Bay sits between emerald-green hills and a crescent of white sand. This all-suite retreat pairs understated style with a sense of space; airy suites framed by palms, cool contemporary lines and the sound of the surf rolling in through open terraces. When night falls, the island’s most sought-after restaurant, East, serves bold Pan-Asian flavours in a sleek, lantern-lit setting.

Then hop over to St Kitts, where Park Hyatt St Kitts Christophe Harbour curves around tranquil Banana Bay. Here, the days blend movement and mindfulness with sunrise hatha yoga, cacao ceremonies on the spa deck and sound healing sessions. Evenings bring golden-hour drinks at Flemings Bar, stargazing or bonfires by the beach, before dinner over the water at Fisherman’s Village or The Stone Barn, where chefs grill local mahi-mahi and caramelised plantains in a rustic-chic dining room – don’t miss family-style trattoria night. When you’re ready to unwind, the sugar mill spa delivers bamboo massages, coconut scrubs and soul-soothing sea views.

Best for romance: Dominica and Saint Lucia

Wild and remote Dominica is effortlessly romantic. The beaches are indeed pretty, but the real beauty lies inland – think tangled rainforests, rustic hotels and hidden volcanic coves. Soak in bubbling hot springs or take a refreshing dip in one of the many waterfalls that don't just look like they've come straight out of a movie, they actually have: many of Dominica's beauty spots were featured in the Pirates of the Caribbean films.  Stay at the five-star eco-hideaway, Secret Bay, which has just 16 high-spec pool villas concealed beneath the forest canopy. 

After your adventures in Dominica, hop on a short flight over to Saint Lucia for jaw-dropping Piton scenery and fiery sunsets. All of these can be seen from every angle at Cap Maison, a clifftop boutique resort that’s made for romance. We love the Kuoni Indulgence Suites that come with exclusive extras such as a couple's massage and a bottle of Champagne.

Browse our latest Caribbean offers here.

This feature was updated on 23rd December 2025. The information within this feature is correct to the best of our knowledge at the time of publication. Feature by Heather Flanagan.