The first night I ever spent in the Caribbean, 25 years ago, was in 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 is no fire,” a security guard assured us. “So what’s all that loud ringing?” I asked. “It’s the sound of tree frogs,” he explains with a smile, “calling for a mate”.
True story – and since then I’ve 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 step off the plane into that comforting warmth, I enjoy the tropical color, sleek rhythms and genuine smiles that greet travelers. Even after making some fifty trips, I still marvel at the brilliant experiences the islands offer, from snorkeling with turtles and climbing volcanoes to bubbly lobster lunches and dinners under the stars where you end up dancing with the hotel staff.
Every winter I am asked where is the best place to go in a charismatic region that offers much more variety than we realize, from idyllic coral reefs to majestic, rainforest-covered mountains and cultural flavors that include French, Spanish, DutchIrish 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-run hotels tucked away in the hills
For a sense of what the Caribbean was like before the mega-cruise ships and 600-room all-inclusive resorts moved in, hop on 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 hardly changed and is still home to characterful, family-run hotels lost in the hills, such as The Hermitage and Montpelier Plantation, which have disappeared elsewhere.
The island has a family tree – Horatio Nelson was married here in 1787 and Diana, Princess of Walesvisited with the young princes in 1992 – while the crowning achievement is the magnificent 3,232-foot climbable Nevis Peak (nevisisland.com).
MY TIP: Check out the Friday night roadside barbecue on the outskirts of the capital, Charlestown. Organized by the island’s Water Department, it’s a great place to meet locals, visitors and expats over some spicy jerk ribs.
BOOK IT: Seven nights at Montpelier Plantation & Beach from £2,225pp B&B, including British Airways flights from Gatwick on March 11 and transfers. Book by 1 March (juststkittsnevis.co.uk).
AUTHENTIC GRENADA
In Grenada base yourself along the two miles of well-maintained sand at Grand Anse Beach
If you like to explore by rental car or excursions, choose this safe and scenic ‘Spice Island’. Grenada – which is a trio of islands – has embraced tourism, but not sold out to it.
People still have time for a chat and the Grenadians really want you to enjoy their homeland, which has an immense mountainous interior where they grow spices, tropical fruits and the cocoa beans used to create award-winning organic chocolate.
Base yourself along the two miles of well-maintained sand at Grande Anse Beach, where options include the luxurious all-inclusive Spice Island Beach Resort and, just beyond, the more affordable Blue Horizons Garden Resort.
You can walk to bars, shops and restaurants and catch a bus to St George’s, one of the most beautiful capitals in the Caribbean.
MY TIP: Visit the 400-acre Belmont Estate in St. Patrick to learn about spices and chocolate, and don’t miss the waterwheel-powered River Antoine rum distillery, founded in 1785.
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 by 15 February (justgrenada.co.uk).
STRESS FREE ANTIGUA
The island has good beaches and is dominated by all-inclusives that run the gamut from cheap and cheerful to dress-for-dinner.
For an easy, fly-and-flop vacation, choose Antigua. There are plenty of flights that last just eight hours and a bit, and within minutes of arriving you’re in vacation mode.
The island has good beaches and is dominated by all-inclusives that run the gamut from the cheap and cheerful Jolly Beach Resort to dress-for-dinner 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 that celebrates its 350th anniversary this year (visit antiguabarbuda.com).
MY TIP: Go for a lazy fish lunch on the tiny island of Little Jumby where a Caribbean outpost of The Hut restaurant, famous on the Isle of Wight, opened 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 20 March and transfers (tropicalsky.co.uk).
SHOOT BACK ON ANGUILLA
There are 33 beaches on this luxury island that’s 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 can’t fail to hit the holiday spot.
There are 33 on this luxury island that’s just 16 miles long with a thriving restaurant scene but no great sights to see. This means you are free to completely relax, enjoy romantic downtime and soul-boosting spa treatments in excellent hotels such as Belmond Cap Juluca and Malliouhana.
If you’re the active type, the sporty Aurora Anguilla Resort has two miles of beachfront, a Greg Norman-designed golf course, and an amusement park with waterslides, pickle ball, and a climbing wall (ivisitanguilla.com).
MY TIP: Book a trip to Prickly Pear Cay for a lobster lunch aboard Tradition, an immaculately restored 45-year-old hand-built sailboat (tradition-sailing.com).
DISCUSS IT: Seven nights at Malliouhana from £6,540pp B&B, including Air France flights from Heathrow to St Maarten via Paris on March 3, and transfers (inspiringtravel.co.uk).
LIVING JAMAICA
Everyone flies in for the beaches, but it is the magnificent scenery inland that captivates me
The largest English-speaking island in the Caribbean has a dynamic spirit that has given the world iconic figures as diverse as Bob Marley, Usain Bolt and, via writer Ian Fleming who lived there, James Bond.
Everyone flies in for the beaches, but it’s the magnificent scenery inland that captivates me, including the World Heritage-listed Blue and John Crow Mountains, which rise to 7,402 feet and produce an exceptionally smooth coffee.
The rum is pretty good too, while Jamaican cuisine is a spicy feast of jerk chicken, beef patties and goat curry, followed by desserts made with mango, pineapple and coconut (visit jamaica.com).
MY TIP: To see the best of this 146-mile-long island stay in two or three locations, including the Blue Mountains. Alternatively, book guided trips through your resort or with Island Routes (islandroutes.com).
BOOK IT: A nine-night small-group tour costs from £2,485pp, departing Kingston on March 19 and including accommodation, transport, activities and breakfast. Flights extra (explore.co.uk).
Do not disturb…
ST MARTINE
It is one of the most densely populated places in the Caribbean and unashamedly commercial with casinos, timeshare resorts and high-rise apartments.
The Dutch half of an island shared with French-speaking St 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 apartments.
If you like duty free shops and tacky souvenirs (windmills, pirate hats, T-shirts that say ‘I’m on a rum diet and lost three days’) then that’s fine.
If not, follow local advice to ‘stay on the French side, party on the Dutch side’.
NASSAU
Nassau is one of the busiest cruise ports in the world and home to the monster resort complex Baha Mar
The Bahamas is a dreamy sprinkling of some 700 islands worth visiting – but don’t waste precious vacation time in this international gateway on New Providence.
Nassau is one of the busiest cruise ports in the world and home to the monster resort complex Baha Mar, with more than two thousand rooms, and Atlantis Paradise Island with more than three thousand.
Instead, head straight for quieter escapes like Harbor Island with its enchanting three-mile Pink Sand Beach.
