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The two Eastern Caribbean islands, located less than an hour apart by plane, are best described as fraternal twins, with both offering very similar vacation experiences (check in to a sprawling resort and, theoretically, never venture off campus). Still, they have their differences. Herewith, each destination’s distinguishing features.


Big, Iconic Resort: Rosewood Jumby Bay is still the opulent classic. On its own private island (ten minutes off Antigua by boat), it just added two palatial villas to book: Lazy Lizard and Harbour Heights. Rooms start at $1,050; St. John’s; 268-462-6000;

Intimate Hotel Alternative: Among the 25 beach- and hillside cottages at Hermitage Bay, nos. 37 to 39 offer the most privacy. You’ll want to sleep with all the windows open—and can, thanks to the mosquito nets over the beds. Rooms start at $920; Jennings; 855-562-8080;

A Home of Your Own: For $50,000 a week, Eric Clapton’s fortress-looking Standfast Point boasts a two-floor main house, two guesthouses, two pools and several terraces with views of Guadeloupe and Montserrat islands. At Standfast Point; 212-213-6435;

No-Frills Local Dining: Tired of seared tuna? Papa Zouk ups the fresh-fish ante with its seafood-loaded bouillabaisse, a Creole-style soup smothered in grated cheese. $ At Hilda Davis Dr.; 268-464-6044.

Activities Beyond the Beach: Antigua is ideal for sailing—it’s cove-dotted, whereas Anguilla has broader beach stretches. Helped by an Atlantic breeze, Nonsuch Bay is a sailors’ hub with more than 20 boats for guests. Rooms start at $118; Hughes Point; 268-562-8000;

Driving Factor: Like most other islands in the region, Antigua requires driving on the left side of the road. Not surprisingly, the majority of its visitors are British.


Big, Iconic Resort: Malliouhana Hotel & Spa once defined what it meant to visit the Caribbean in style. Now it’s poised to rise again when it reopens in February after a multimillion-dollar, nine-month makeover by Auberge Resorts. Rooms will start at $650; Meads Bay; 866-282-3743;

Intimate Hotel Alternative: Cap Juluca’s domed roofs might call to mind the resort’s mid-1980s heyday. But the suites (inside 18 villas) have evolved. Case in point: The recently rebuilt Jonquil Suite has two bedrooms and an infinity pool. Rooms start at $495; Maundays Bay; 264-497-6666;

A Home of Your Own: From the outside, the newly renovated Cerulean Villa on Barnes Bay looks like it could belong on Malibu’s Billionaire’s Beach. But inside, the nine suites couldn’t feel more island. From $200,000 a week; 212-213-6435;

No-Frills Local Dining: Take a break from red snapper: The Jamaican chef’s spiced curried goat at Smokey’s at The Cove is so tender, it practically falls off the bone. At Cove Bay; 264-497-6582;

Activities Beyond the Beach: For one of the few places to tee off in the Eastern Caribbean, head to CuisinArt’s Greg Norman–designed 18-hole golf course, which will be all the more appealing when the resort adds a new 62-room golf hotel in October 2015. Rooms start at $325; greens fees, at $145; Rendezvous Bay; 264-498-2000;

Driving Factor: Like in Antigua, cars are driven on the left, but many rental cars have U.S.-style steering wheels on the left-hand side, which might help explain why it’s a favorite among American travelers.

$ Establishment accepts no charge/credit cards or accepts cards other than the American Express Card.


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