The first night I spent in the Caribbean, 25 years ago, was at a small beach resort in Jamaica with my wife and two young children. Around 2am we heard a fire alarm go off and immediately ran out of our room in a panic.
“But there’s no fire,” a security guard assured us. —So, what is the reason for that loud noise? I asked. “It’s the sound of tree frogs,” he explained with a smile, “asking for a mate.”
True story, and since then I have been lucky enough to visit 27 Caribbean islands and territories, from the Bahamas to Tobago via Aruba, including forgotten corners like St. Eustatius, Montserrat and Bonaire.
Every time I get off the plane and feel that comforting warmth, I enjoy the tropical color, the melodious rhythms and the genuine smiles with which travelers are greeted. Even after making about fifty trips, I still marvel at the brilliant experiences the islands offer, from snorkeling with turtles and climbing volcanoes to lobster lunches and dinners under the stars where you end up dancing with the hotel staff.
Every winter I am asked what is the best place to go in a charismatic region that offers much more variety than we think, from idyllic coral cays to majestic rainforest-covered mountains and cultural flavors that include French, Spanish, Dutch, Irish and Creole. While each island has its charms, these are my all-time favorites.
OLD SCHOOL NEVIS
In the 16 years I’ve been visiting, Nevis has barely changed and is still home to characterful family hotels lost in the hills.
To get a sense of what the Caribbean was like before mega-cruise ships and 600-room all-inclusive resorts arrived, take a flight to St Kitts and then take the short boat transfer to its quieter sister island.
In the 16 years I’ve been visiting, Nevis has barely changed and is still home to characterful family hotels lost in the hills, such as The Hermitage and Montpelier Plantation, that have disappeared elsewhere.
The island has pedigree – Horatio Nelson married here in 1787 and Diana, Princess of Wales, visited the young princes in 1992 – while the crowning glory is the magnificent, climbable 3,232-foot Nevis Peak ( nevisisland.com). ).
MY ADVICE: Attend the Friday night roadside barbecue just outside the capital, Charlestown. Hosted by the island’s Water Department, it’s a good place to meet locals, visitors and expats over spicy ribs.
BOOK IT: Seven nights at Montpelier Plantation & Beach from £2,225pp bed and breakfast, including British Airways flights from Gatwick on March 11 and transfers. Book before March 1 (juststkittsnevis.co.uk).
AUTHENTIC POMEGRANATE
In Grenada, make your base next to the two kilometers of well-maintained sand at Grand Anse Beach.
If you like to explore by rental car or go on excursions, choose this safe and picturesque “Spice Island”. Grenada – which is a trio of islands – has embraced tourism but has not sold itself to it.
People still have time to chat and Grenadians really want you to enjoy their homeland, which has a tremendous, mountainous interior where they grow spices, tropical fruits and the cocoa beans that are used to create award-winning organic chocolate.
Sit next to two miles of well-maintained sands at Grande Anse Beach, where options include the luxurious all-inclusive Spice Island Beach Resort and, just behind, the more affordable Blue Horizons Garden Resort.
You can walk to bars, shops and restaurants and take a bus to St George’s, one of the most beautiful capitals in the Caribbean.
MY ADVICE: Visit the 400-acre Belmont Estate in St Patrick to learn about spices and chocolate, and don’t miss the River Antoine Rum Distillery, founded in 1785, powered by a waterwheel.
BOOK IT: Seven nights at Spice Island Beach Resort from £5,440pp all-inclusive, including Virgin Atlantic flights from Heathrow on March 4 and transfers. Book before February 15 (justgrenada.es).
OLD WITHOUT STRESS
The island has good beaches and is dominated by all-inclusive hotels that run the gamut from cheap and cheerful to fine dining.
For an easy and highly successful vacation, choose Antigua. There are many flights that only last eight or so hours, and within minutes of arriving you are in vacation mode.
The island has good beaches and is dominated by all-inclusive hotels that run the gamut from the cheap and cheerful Jolly Beach Resort to the chic Curtain Bluff, with water-skiing and caviar spa treatments.
Some are isolated, so check a map before booking, but nowhere on the island is more than a 45-minute drive away.
English Harbor is the star attraction with its World Heritage-listed Nelson’s Dockyard, a Georgian-era naval dock celebrating its 350th anniversary this year (visitantiguabarbuda.com).
MY ADVICE: Enjoy a leisurely fish lunch on the small island of Little Jumby, where a Caribbean outpost of the Isle of Wight’s popular restaurant The Hut opened its doors in November (thehutlittlejumby.com).
BOOK IT: Seven nights at The Inn at English Harbor from £4,219pp half board, including Virgin Atlantic flights from Heathrow on March 20 and transfers (tropicalsky.es).
BACK IN ANGUILLA
There are 33 beaches on this luxury island that is just 16 miles long with a thriving restaurant scene but no great sights to see.
In my opinion, this low-lying British Overseas Territory has the best beaches in the Caribbean, lined with clean white sand and turquoise waters that cannot fail to be a holiday spot.
There are 33 on this upscale island that’s just 16 miles long with a thriving restaurant scene but no great sights to see. That means you can completely relax, enjoy romantic downtime and soul-revitalizing spa treatments at superlative hotels like Belmond Cap Juluca and Malliouhana.
If you’re the active type, the sporty Aurora Anguilla Resort has a two-mile beach, a Greg Norman-designed golf course, and an entertainment park with water slides, pickleball, and a climbing wall (ivisitanguilla.com).
MY ADVICE: Book a trip to Prickly Pear Cay to enjoy a lobster lunch sailing aboard the Tradition, a 45-year-old handcrafted sailboat that has been impeccably restored (tradition-vela.com).
BOOK IT: Seven nights at Malliouhana from £6,540pp bed and breakfast, including Air France flights from Heathrow to St Maarten via Paris on March 3 and transfers (inspirationaltrips.es).
VIBRANT JAMAICA
Everyone flies to go to the beaches, but what captivates me is the magnificent landscape of the interior.
The largest English-speaking island in the Caribbean has a dynamic spirit that has given the world iconic figures as varied as Bob Marley, Usain Bolt and, through resident author Ian Fleming, James Bond.
Everyone flies to the beaches, but what captivates me is the magnificent scenery inland, including the World Heritage-listed Blue and John Crow Mountains, which rise to 7,402 feet and produce exceptionally smooth coffee.
The rum is pretty good too, while Jamaican cuisine is a spicy feast of marinated chicken, beef burgers and goat curry, followed by desserts made with mango, pineapple and coconut (visitjamaica.com).
MY ADVICE: To see the best of this 146-mile-long island, stay in two or three places, including the Blue Mountains. Alternatively, book guided tours through your resort or with Island Routes (islandroutes.com).
BOOK IT: A nine-night small-group tour costs from £2,485 per person, departs Kingston on March 19 and includes accommodation, transport, activities and breakfast. Extra flights (explore.co.uk).
Don’t bother with…
SAINT MARTIN
It is one of the most densely populated places in the Caribbean and unabashedly commercial, with casinos, timeshare resorts and high-rise condominiums.
The Dutch half of an island shared with French-speaking Saint Martin is a useful transport hub, served by flights from Amsterdam and Paris, but there’s no need to linger.
It is one of the most densely populated places in the Caribbean and unabashedly commercial, with casinos, timeshare resorts and high-rise condominiums.
If you like duty-free shopping and tacky souvenirs (windmills, pirate hats, T-shirts that say “I’m on a rum diet and wasted three days”), then that’s fine.
Otherwise, follow local advice to “stay on the French side and party on the Dutch side.”
NASSAU
Nassau is one of the busiest cruise ports in the world and is home to the monster Baha Mar resorts.
The Bahamas is a dream group of around 700 islands worth visiting, but don’t waste your valuable vacation time at this international gateway to New Providence.
Nassau is one of the busiest cruise ports in the world and is home to the monster resorts Baha Mar, with more than two thousand rooms, and Atlantis Paradise Island, with more than three thousand.
Instead, head straight for quieter getaways like Harbor Island with its mesmerizing three-mile-long Pink Sand Beach.