Famed for its pink sand beaches, British history, and quick two-hour flight from New York City, Bermuda is experiencing a sexy new awakening as host to the 35th America’s Cup yacht race. Qualifying races start May 26 on the Great Sound; the top challenger will take on defending champ Oracle Team USA beginning on June 17. Don’t forget to dress the part: Pick up your bold-colored Bermuda shorts and racing-print swim trunks from the America’s Cup collection at the cheerful TABS flagship store (12 Reid Street, Hamilton).

Colorful options at TABS Bermuda.

Host hotel Hamilton Princess & Beach Club recently capped a multiyear remodel with a renovation of Marcus Samuelsson’s restaurant overlooking Hamilton Harbor. (Shoot the breeze over a Darker and Stormier, his version of Bermuda’s classic cocktail.) The property is offering five-night stays that include passes to the finals and a visit to the America’s Cup village (doubles from $1,005 per night; five-night minimum).

Race fans at Rosewood Tucker’s Point can reserve spots on the elegant 1926 Mariner III, an 80-passenger yacht that provides prime viewing with hotel-catered cuisine and cocktails (doubles from $1,395; Mariner III race viewing from $295).

Here are more of my favorite discoveries from a recent escape to the island:

Wahoo’s Bistro

Stop at Wahoo’s in historic St. George’s after you land in Bermuda – just ten minutes from the airport – for the best (and enormous!) fish tacos and award-winning Bermuda Fish Chowder. It’s owned by Austrian expat and chef Alfred Konrad (hence, a schnitzel sandwich on the menu), and everything is super fresh and comes with a great patio view (36 Water Street, St. George’s).


Far from Hamilton’s tourist crowds, this hearty neighborhood Italian spot in Flatts Village hits the spot. Order pizzas to share and sit on the patio on a beautiful night. You’ll be surrounded by locals – or vacationers with second homes on the island – which makes for great people-watching (North Shore Road, Flatts Village).

Della Valle Sandals

Italian Vincenzo Della Valle has made shoes since he was a child living in Capri. Last summer, he finally opened his long-dreamt of shop on Hamilton’s Queen Street, a must-stop for well-priced, custom women’s sandals. Go on your first day in Bermuda so Valle has time to finish them before you leave – he doesn’t ship (depending on your order, turnaround time is a couple of days). If I regret one thing about my trip, it’s buying only one pair (19 Queen Street, Hamilton).

Vincenzo Della Valle works on a pair of custom sandals in Hamilton, Bermuda.

Gibbs Hill Lighthouse

Climb 185 steps to the top of this historic lighthouse in Southampton Parish for a panoramic view of the entire island. Queen Elizabeth II visited the lighthouse shortly after her coronation on June 2, 1953 – one of four trips she has made to Bermuda.

The view from Gibbs Hill Lighthouse.

Masterworks Museum of Bermuda Art

This museum only shows art inspired by Bermuda, including famous pieces by Winslow Homer and Georgia O’Keeffe. It’s one of the best small museums I’ve visited anywhere – Prince Charles is an official patron. Viewing Bermuda through artists’ eyes helps you appreciate its landscape, people, and culture (such as sailing and races) even more. If you see curator and director of collections Elise Outerbridge, ask her about her encounters with David Bowie, who had a home on the island. Stroll through the small Bermuda Botanical Gardens surrounding the museum after your visit (183 South Road, Paget).

Masterworks Museum of Bermuda Art.

Tip: As of May 2017, rental cars are banned on the island – even residents are permitted only one car per family. Have your travel advisor reserve their favorite driver and/or guide, or book taxis through the hotel.

All photos by Annie Fitzsimmons.