The best islands in the Caribbean
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I’ve been fortunate to travel widely across the best islands in the Caribbean over the last 30 years. I’m also a descendant of Caribbean people, so many folks assume I’ve visited every island. Not likely – the Caribbean consists of 28 islands encompassing just over one million square miles. So while I’ve visited most, there are still a handful I’ve yet to encounter. But that’s a good thing. Many know the Caribbean of picture postcard views – all lush green hillsides, soft beaches, sunny skies, sun loungers and poolside cocktails. But that’s really just the white-sandy surface of this region, where each island has something distinct to offer. On Dominica, hiking is unmatched, notably its Boiling Lake, a flooded fumarole located in Morne Trois Pitons National Park, where you can traverse across the rim of an active volcano. The best island hopping is in the British Virgin Islands, while Barbados is the action island, where the historic Garrison horse racing takes place year-round.
If you’re looking to soak up some winter sun by a pool lounger and nothing more, then any island in the Caribbean will do – the hotels in St Barth's are amongst some of the best in the world. But if you’re willing to dig a little deeper and venture beyond the resort gates, these are the best islands in the Caribbean.
Which is the best Caribbean island for families?
When little travellers are involved, the ease of a resort jam-packed with activities can take the strain off parents and let everyone enjoy the trip. For this reason, Barbados is the best island to go to in the Caribbean for families, and there’s everything from larger, more affordable resorts to smaller boutique offerings. For intergenerational holidays and trips with slightly older children, consider hiring out a villa – Oliver’s Travels allows customers to filter results by ‘great for kids’.
What is the prettiest Caribbean island to go to?
We don't like to pick favourites, especially when beauty is so abundant as it is in the Caribbean. However, if we must, then we'd recommend St Lucia as the prettiest island in the Caribbean. St Lucia is well known for its stunning Piton mountains, a UNESCO World Heritage Site that offers some of the best views in the Caribbean. The island is green, lush and blessed with incredible beaches.
Best islands in the Caribbean at a glance
- Best Caribbean island for beaches: Anguilla
- Best Caribbean island for diving: Dominica
- Best Caribbean island for honeymoons: St Lucia
- Best Caribbean island for island hopping: British Virgin Islands
- Best Caribbean island for families: Barbados
Getty Images1. Barbados
Best island for: action
Barbados might just be one of the best all-rounder islands in the Caribbean. Some of the top hotels in the region are found here, as are some of the best beaches, all accessible to the public – there are no private beaches in Barbados. Poolside beverages are spiked with rum, distilled on the island and best learnt about at St Nicholas Abbey, a plantation house, museum and rum distillery. Those looking for more diverse action can find it at the heritage railway, the racing car circuit and the Garrison Savannah, a popular horse race that takes place throughout the year. And then there are the surrounding reefs, where you can swim with turtles, snorkel with seahorses and spy whales in winter months.
Where to stay: Sandy Lane Hotel is one of the most glamorous hotels on the island complete with a British or American country club vibe – there are three golf courses on the hotel grounds. For something more low-key, Little Good Harbour’s rooms feel more like private cottages and its fuss-free restaurant, The Fish Post, is beloved as one of the best in Barbados. For more recommendations, see our best hotels in Barbados guide. Brian Major
Getty Images2. Harbour Island
Best island for: an indulgent holiday
Harbour Island is incredibly small compared to the likes of Puerto Rico, but it packs a serious punch. A hop, skip, and a jump from Jamaica, and you'll find yourself on a three-mile-long island that is the pure embodiment of island life: sandy feet, salty hair and pops of colour from the pastel-coloured 19th-century colonial cottages. The atmosphere exudes warmth, and with a small population of about 2,000, it's easy to understand why travellers fall in love with the sense of community on Harbour Island. That's not to say it doesn't have its fair share of the lavish lifestyle – one side of the island boasts superyachts, upscale boutiques and a slew of restaurants, including my favourite, Da Vine, a delicious sushi spot. But travel to the other side of the island and you'll find Pink Sands Beach, one of the Bahamas' most beautiful beaches, that I found shines even brighter at sunset. Harbour Island is paradise, and if you're looking for a holiday that balances luxury and laidback beach vibes, then this is the Caribbean island for you.
Where to stay: I recommend Eleven Bahama House, an absolute gem that perfectly embodies quiet luxury. Dusty pink buildings give way to 11 double bedrooms, each with a unique style that celebrates the colour and warmth that defines Harbour Island. Amber Port
Getty Images3. St Lucia
Best island for: romance
The Caribbean is synonymous with honeymoons, but St Lucia tops them all when it comes to serving up romance. You can thank the island’s mountainous landscape for that – it’s all about a room with a view of the 2,000-foot-high Piton mountains, a UNESCO World Heritage Site and the island’s calling card.
There’s adventure to be found too, like exhilarating ziplines high above the island’s rainforest canopy or mud baths in Sulphur Springs, a geothermically active basin of hot springs and fumaroles within the the dormant Qualibou volcano in Soufrière
Where to stay: Coconut Bay is the biggest crowd pleaser on the island – an all inclusive resort catering to couples, families and even wedding parties. For something more private, Ladera is an eco-lodge where rustic suites have private plunge pools. See our edit of the best hotels in St Lucia for more. Brian Major
Getty Images4. Anguilla
Best island for: beaches
In a region characterised by beautiful beaches, Anguilla has the best in the region. Partly for their mesmerising ribbon of blue water but also because their powdery white sand beaches invariably host only a handful of other beach-goers. There are 33 stunning beaches in total, and while each one I’ve encountered has been memorable, the standouts to see include Cove Bay, Maundays Bay, Rendezvous Bay and Shoal Bay.
Anguilla is also a worthy choice for its culinary scene. Refreshingly there are no chain restaurants on the island. Instead, restaurants and eateries tend to be small family-run businesses. If you visit just one, make it Tasty’s, which serves up a stellar coconut-crusted fish and marinated conch salad by Anguillan chef Dale Carty.
Where to stay: The Aurora Anguilla Resort & Golf Club is the newest shiny address on the island, with seven restaurants and bars and a fleet of private jets transporting guests to and from the property. Brian Major
Getty Images5. British Virgin Islands
Best island for: island hopping
The British Virgin Islands (BVI) territory has few chain restaurants and no large hotels or mass tourism attractions. Instead, you’ll encounter turquoise waters, lush green hillsides and distinctive cuisine and culture across the four main islands: Anegada, Jost Van Dyke, Tortola and Virgin Gorda.
Hopping from island to island – whether via public ferry or private catamaran – is the characteristic way to explore the BVI. On my last visit, I sailed to Jost Van Dyke’s White Bay, home to casual beachfront eateries serving dangerously delicious rum cocktails and locally caught fish. Another fantastic spot is Willy T’s Floating Bar and Restaurant near Norman Island. Moored offshore, the cargo ship has been converted into an ultra-relaxed eatery.
Where to stay: Located on a broad, secluded calm-water bay on Virgin Gorda, Rosewood Little Dix Bay has 80 villas and suites each staffed with a personal butler. The Reef House is one of three restaurants and features farm-to-fork dining with fresh provisions sourced locally. Brian Major
Getty Images6. Dominica
Best island for: diving
The calm waters surrounding Dominica make it one of the best diving spots in the world. The rainbow-coloured seascape is best viewed at Champagne Reef, named for its bubbling waters generated by volcanic thermal springs rising from on the ocean floor. The reef also comprises plummeting cliffs, towering volcanic formations and the remains of a 17th-century Spanish shipwreck.
Another highlight is L'Abym, a dive site located on the island’s southern tip and suited to all skill levels due to Soufriere Bay’s gentle current. Underwater wonders are visible from 20 feet below the surface right down to a 1,500-foot maximum depth. An underwater wall extending its entire length gives the site its name.
Where to stay: Cabrits Resort & Spa Kempinski is the smartest place to stay on the island. All of the classic hallmarks are here – a full-service spa and four swimming pools – but it’s the lush grounds, which incorporate Cabrits National Park, that make this spot memorable. Brian Major
Getty Images7. Grenada
Best island for: natural beauty
Grenada’s 133 archipelagic square miles are laced with waterfalls, hot springs and tropical rainforests across three main islands: Grenada, Petit Martinique and Carriacou. Ringed by 45 white- and nine black-sand beaches, the hilly isles are dotted with acres of fruit and spice trees.
One-ninth of Grenada’s land mass is dedicated to national parks and wildlife sanctuaries, best seen on a guided hike of Grand Etang Forest Reserve. Sister Island Carriacou is a worthy day trip too, especially for the top-shelf diving and snorkelling.
Where to stay: Few places capture Grenada's understated magic like the Silversands Grenada resort, found at the sleepy end of the two-mile Grand Anse Beach. The biggest draw here is the 330-foot infinity pool, said to be the longest in the Caribbean, which stretches from the hotel’s entrance all the way to the sea. Brian Major
Getty Images8. Puerto Rico
Best island for: history and culture
There’s a distinct energy to Puerto Rico, one that draws upon a fascinating blend of Hispanic, African, USA and Caribbean culture and history. To see it start in colonial San Juan, the second oldest European-founded city in the Americas. Head to the old town where cobblestone streets are lined with colourful Spanish buildings housing trendy bars, boutique shopping and all-night entertainment.
Hundreds of thousands of Africans arrived in Puerto Rico via forced migration in the colonial era. Their contributions to the island’s culture, art, music and cuisine live on today in Loiza, home to Puerto Rico’s largest Black population. You can witness it via the artwork on display at Samuel Lind Studio, or at the Don Rafael Cepeda School of Bomba and Plena which puts on traditional music and dance workshops.
Where to stay: Caribe Hilton is within walking distance of historic Old San Juan and the Condado entertainment district. Designed in tropical modernist style by legendary Puerto Rican firm Toro Ferrer, the grounds incorporate 17 acres of tropical landscaping as well as nine restaurants and an oceanfront pool complex. Brian Major
Getty Images9. St. Kitts and Nevis
Best island for: visiting two islands in one trip
Lush natural beauty and historic attractions are the hallmarks of this twin-island nation. Most travellers visit both islands, as smaller Nevis is a breezy 20-minute ferry ride from larger St. Kitts. Sightseeing on St. Kitts is best done via the scenic train – the only working railway in the Caribbean – which circumnavigates the island on routes that once transported plantation sugar cane. Another highlight is the Brimstone Hill fortress, built of hand-chiseled stones by enslaved Kittitians and now a UNESCO World Heritage Site. Stand among the fort’s ramparts and cannon while taking in panoramic views of neighbouring Saba, Statia, St. Maarten and St. Barths.
Tiny Nevis’ resplendent landscape is overlooked by 3,232-foot high Nevis Peak, located at its center and visible from virtually every point on the island. Mountainside hiking and ATV tours uncover haunting ruins of colonial-era plantations and sugar mills.
Where to stay: Hideaway in one of the traditional West Indian-inspired cottages at Belle Mont Farm. As the name suggests, dining here is farm-to-table, serving up freshly foraged organic fruit and vegetables plus seafood plucked straight out of the ocean. Brian Major