For a taste of Italy in the Caribbean, head to Antigua, a onetime British colony nestled in the middle of the West Indies. It’s easy to get to—direct flights are available from New York and Milan and land at the newly refurbished terminal at V.C. Bird International Airport. From there it’s a quick taxi ride to the Inn at English Harbour (rooms from $763; + 1 268 460-1014), where the Italian owners have renovated the 28 rooms to feel like a sun-washed villa. The hotel’s private beach is near the Galley Bay Heights home of Giorgio Armani; fellow Italian designer Stefano Gabbana is also an island regular. Grab breakfast at Famous Mauro’s pizzeria (+ 1 268 460-1318) near Cobbs Cross, where bakers repurpose the pizza ovens to make the island’s best brioche.
If sailing is your thing, the world’s finest vessels gather for the annual Antigua Classic Yacht Regatta, a five-day competition in April that takes place in and around the island’s deep-water harbors. This year, watchmaker and sponsor Panerai is competing with a restored 1936 Bermudan ketch, which is sailing over from her permanent berth in San Remo. Those with traditionally made boats—typically built of wood before 1970—can register via the event’s website ($8 per foot before April 1, $12 per foot after).
The best view of the action is from Antigua’s top drinking spot, Catherine’s Café Plage (+ 1 268 460-5050). Have a glass of homemade ti’ punch, made with rhum agricole, sugar, and lime, and pair it with a steak or lobster tartare. For dinner, eat at Rum Baba (268 770-2672), a nearby cafe that serves Mediterranean fusion food. Later, swing by Abracadabra (+ 1 268 460-2701), a restaurant founded by Sardinian yachtsman Carlo Falcone, who came to the island 30 years ago and never left. Try an order of suckling pig, or porceddu, then linger until late, when the place transforms into a Sorrento-style dance club.
Antigua’s rugged sister island, Barbuda, about 40 miles north, can be reached in 90 minutes by boat. If you stay overnight, the new Barbuda Belle (rooms from $890; + 1 646 652-7311) is set along a 17-mile pink sand beach, and each of the six wooden bungalows comes with four-poster beds and al fresco showers. The food at the restaurant Mangrove is delicious, though French. Close enough.
Back on Antigua Jacqui O’s Love Beach (+ 1 268 562-2218) has a similar St Tropez-in-the tropics vibe, albeit with louder music. Try one of the house specials, Blue Lada, a rum punch spiked with slugs of blue curaçao and elderflower cordial.
In 1962, the owners of Curtain Bluff, Howard and Chelle Hulford, had intended to build themselves a home, but instead opened a hotel, perched on a spectacular cliff on the southern coast. The 72-room property, set on a 20-acre lush garden, is still a family-run, all-inclusive affair (tennis and sailing are comped, too). Its best asset, though, is the house rum punch, laced with coconut cream. This season, it’s adding a private pool on the terrace of each ocean-facing suit. (Rooms from $1,265)
On the west coast of the island, Hermitage Bay is a newer resort, celebrating its 10th anniversary this year; it’s a passion project from first-time hotelier Andy Thesen. The 27 airy rooms have Aman-like neo-Asian interiors—book one of the 10 that sit directly on the wide sand beach. The entire compound is discreetly eco-aware, from the louvered shutters to keep rooms breezy to the onsite cottage garden providing fresh-picked produce for that evening’s menu. (Rooms from $970)
There’s ample diving with the coral reefs rimming Antigua teeming with parrot and angelfish. Book a trip with Dockyard Divers: the Pillars of Hercules site is a 3-minute boat ride, ideal for beginners, while Cape Shirley, with its huge boulders and depths of up to 110 feet, is for more experienced divers. There’s also the sandy-floored Stingray Alley, where scores of the namesake animals lurk.
Cricket is the national past time, and iconic international ace Viv Richards, the wicket-keeping answer to Babe Ruth, was born here. Watch some local teams at the Antigua Recreation Ground on Factory Road in St John’s during season, which ends in April this year.
Whether the actual tally of beaches here is 365, or one per day, as brochures claim, there are outstanding sands—windsurf off the edge of Atlantic-facing Half Moon Bay, or dawdle on the deserted Johnson’s Point with its warm Caribbean waters. The trade winds cool the sands of Turner’s Beach near the latter, making it especially pleasant for sunbathing.