One of the Leeward Islands of the West Indies, this southern Caribbean isle has the right mix of posh (famous fans include Giorgio Armani, Eric Clapton, Richard Branson, and Oprah Winfrey), relaxed (it’s home to endless strands of sands), and authentic Caribbean flavor. Ships dock in St. John’s, Antigua’s capital city that’s robust with local shops and historic sites, including a cathedral whose third incarnation was built in 1845 after earthquakes destroyed the first two.
What We Love
Hiking Trails: About a 30-minute hop from port, you can find a series of paths that wind above English Harbor. Some lead to hidden beaches, and all have stunning water and island views.
Harmony Hall: This sprawling former sugar plantation now has a restaurant, an art exhibition area, and a fantastic beach.
Best Known For
Pigeon Point Beach: Tree shaded and easily accessible, this popular duo of strands is loaded with day amenities, strolling opportunities, and snorkeling spots.
Nelson’s Dockyard: Once home of the British fleet in the Caribbean, this nautical outpost is one of the best-maintained sites in the Caribbean. Pastel buildings, constructed in the 18th century, house restaurants, shops, and a comprehensive maritime museum.
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Who It's Best For
Beach Bums: Locals like to say Antigua is home to 365 beaches — one for each day of the year. Hop in a cab and tell your driver to take you to his favorite, or the best one for your favorite activity, whether it's strolling, sunning, kayaking, or skinny dipping.
Sailing Buffs: A host of islets and tiny anchorages are in the waters surrounding the main island of Antigua. Barbuda, a sister island that’s actually a coral atoll, is a scenic site robust with wildlife and 14 miles of pristine pink beaches.
Don't Say We Didn't Warn You
Not a Duty-Free Delight: Unlike neighboring islands in the region, this former British colony isn’t robust with duty-free outposts. Instead, check out the local art, crafts, and ceramics on offer for a more authentic souvenir.
Jenna Mahoney is a Brooklyn-based contributor to ShermansCruise who has also written for Allure.