When in season, sampling stone crab claws - a local delicacy - is a must. For a hearty snack, enjoy the succulent ham, Swiss cheese, and salty pickles that make a Key West Cuban sandwich.
Old Town
Duval Street cuts through Old Town, lined with grand 19th century mansions, independent art galleries, and quaint chapels. For delicate dishes, try Nine One Five – a sleek bar and restaurant set in a white-washed wooden Victorian house. Grab a table on the old porch, and treat yourself to the beef carpaccio or confit duck. Save space in your belly, though, as there's also the distinctively named Better Than Sex – Key West’s only dessert restaurant. Here you'll enjoy decadent chocolatey desserts amid romantic red and gold décor.
• Nine One Five, 915 Duval Street, Key West; • Better Than Sex, 926 Simonton Street, Key West;
New Town
New Town is the modern eastern neighborhood of Key West, where shoppers flock to explore the clothing stores in the vast shopping malls. There's some good eating to be had here too. For a slice of ocean-side perfection, head to the inexpensive, family-friendly La Trattoria, and enjoy authentic Italian cuisine. If you’re after a taste of true American-style dining, there’s no beating the luxury candle-lit setting of Tavern N Town, which serves up juicy, peppery steaks alongside craft beers.
• La Trattoria, 3593 S Roosevelt Blvd, Key West; • Tavern N Town, 3841 N Roosevelt Blvd, Key West;
Mallory Square
Overlooking the sun-spangled Gulf of Mexico, this large plaza is home to the Sunset Celebration, where tourists and locals flock to view the fiery orb of the sun dip down over the ocean. This is a great place to discover Key West’s food trucks, which cook up spicy Cuban cuisine, from fat sandwiches to zingy rice dishes. If you’d prefer a sit-down dining experience, head to the family-owned El Meson de Pep, and enjoy the shrimp in Creole sauce and Cuban-roasted pork. For some stellar takeaway or no-fuss in-house eating, visit the cabana-themed Juan Loves Lucy, and don’t forget to sample the seriously spicy house hot sauce.
• El Meson de Pep, 410 Wall Street, Key West; • Juan Loves Lucy, 124 Duval Street, Key West;
Casa Marina
The Casa Marina takes its name from the Casa Marina Waldorf Astoria Resort, a luxury island retreat conceived by American railroad tycoon Henry Flagler. The resort still stands, and is now surrounded by large, luxurious houses and wide palm-lined streets that lead from Midtown to the sandy southern Key West beaches. For a first-rate dining experience, head to the Caribbean-American restaurant Louie’s Backyard, which boasts ocean views and top-of-the-range seafood cooking. For some budget eats, head to local favorite Sandy’s Cafe, a 24-hour diner-style sandwich joint.
• Louie’s Backyard, 700 Waddell Ave, Key West; • Sandy’s Cafe, 1026 White St, Key West; Tel: +1 305 2950 159
