Key West, FL

A family-run Cuban kitchen off the tourist track that locals have leaned on since 1984, serving ropa vieja, vaca frita, and butterflied yellowtail with yellow rice and brothy black beans. Big portions, fair prices, and zero pretense under a tin roof. Best for a hearty, honest lunch that fuels a long island day.

A famously laid-back Caribbean breakfast in a Bahama Village courtyard where roosters strut between the tables and the key lime pie towers under a cloud of meringue. The shrimp eggs Benedict and banana-walnut pancakes are the morning move. Best for a leisurely, only-in-Key-West breakfast you'll be glad you waited for.

A working-waterfront fish house on Stock Island where the catch comes off the boats just outside, and the hogfish sandwich is the thing to order. It's the unvarnished, salty Keys experience the resorts try to imitate. Best for a no-frills seafood lunch among shrimpers and locals.

A newer Stock Island spot from a crew of longtime local chefs and fishermen, set on a working dock where shrimp boats glide past your table. The cooking puts creative spins on the raw bar and whatever came in fresh that day. Best for fresh seafood with a bit more ambition than the classic shacks.

A gloriously ramshackle fish shack built of driftwood and license plates in the middle of Old Town, slinging fried grouper sandwiches from a converted wagon. It looks like it might collapse and that's exactly the appeal. Best for a messy, memorable lunch and live music when it strikes up.

A food-truck-turned-local-legend doing Korean-Mexican mashups, with mango-jalapeno fish tacos that punch far above their humble setup. Fresh, fast, and cheap in a town where neither is guaranteed. Best for a quick, bright lunch when you don't want a sit-down production.

A dim, romantic tapas room in Bahama Village turning out a long list of small plates from patatas bravas to ceviche, meant to be shared over a bottle. It's the locals' answer to a fun, graze-y dinner away from the Duval circus. Best for a group that wants to order half the menu.

A genteel Caribbean-American dining room in a historic Victorian with a deck hanging right over the Atlantic at the island's south edge. It's the special-occasion table locals have trusted for decades. Best for a sunset dinner or a drink at the Afterdeck bar with your toes near the water.

An eclectic, globally-minded kitchen set across the porches of a restored Victorian mansion on upper Duval, where the small-plate menu changes with what's good. The wraparound veranda is one of the prettiest places to eat on the island. Best for a relaxed, grown-up dinner that still feels distinctly local.

A tiny wood-fired pizzeria near the seaport doing blistered Neapolitan-leaning pies and handmade pasta in a town short on real Italian. It punches well above its few tables. Best for a casual, unfussy dinner when you need a break from seafood.

A walk-up window attached to a laundromat on White Street pouring strong Cuban coffee and pressing cheap, excellent Cuban sandwiches. It's a pure locals' ritual with nowhere to sit and no reason to. Best for a cafe con leche and a sandwich to go on the way to the beach.

A bright waterfront walk-up near the marinas serving cafe con leche, Cuban breakfast sandwiches, and a respectable Cuban mix to a steady line of regulars and crews. It's the morning fuel stop before a boat day. Best for breakfast on the move down by the Historic Seaport.

The island's key lime headquarters, best known for the chocolate-dipped key lime pie on a stick that's become a Key West rite of passage. There's pie, key lime everything, and the owner posing out front. Best for a sweet stop near the seaport with something the kids will remember.

An organic cafe and juice bar near the seaport leaning into bowls, wraps, smoothies, and plant-forward plates, a genuine rarity on a fried-fish island. The attached market sells healthy provisions for self-caterers. Best for a light, fresh meal or a green juice to reset after a few indulgent days.

The paved rail-trail that shadows US-1 up the keys, with the lower-keys sections offering flat, breezy riding and walking over old bridges and past mangrove flats. From Stock Island you can string together miles of car-free coastline. Best for a cycling morning that gets you out of town along the water.

The only frost-free botanical garden in the continental US, with shaded nature trails winding through native hardwood hammock, freshwater ponds, and migratory-bird habitat on Stock Island. It's a cool, quiet green pocket most visitors never reach. Best for a calm nature walk and birdwatching away from the crowds.

A short boardwalk over salt ponds and mangroves near the airport, threading a slice of native wetland that survives in the middle of New Town. It's flat, quick, and surprisingly birdy. Best for a brief nature stop or sunrise birdwatching close to the residential side of the island.

A small native-plant park and wildlife-rehab center in Old Town with a quiet looping trail through tropical hammock and a pond of resident birds. It's a peaceful pause a few blocks from the beach. Best for a short, shaded walk and a look at recovering native wildlife.

A long, flat concrete pier reaching into the Atlantic off Higgs Beach, the local spot for sunrise walks, fishing, and a stroll past the AIDS Memorial and the historic African Cemetery site. It's a calm waterfront promenade away from Duval. Best for an easy morning or evening walk with open-water views.

A museum built around treasure hauled from the 1622 wreck of the Atocha, with gold bars you can touch, emeralds, and the story of a decades-long salvage obsession. It's a tight, genuinely thrilling hour of real sunken treasure. Best for a rainy afternoon or anyone who's ever daydreamed about shipwrecks.

A glass-domed conservatory filled with hundreds of free-flying butterflies, tropical birds, and a pair of resident flamingos in a warm, misty garden. It's calm, beautiful, and a guaranteed hit with kids. Best for a gentle indoor escape from sun or rain near the Southernmost Point.

The island's contemporary arts hub, with rotating gallery shows, resident artists' studios, and a calendar of talks, music, and the popular rooftop events. It's where the local creative scene actually gathers. Best for an evening event or a quick gallery browse with a view.

The southernmost brewery in the US, set in the historic building where Pan Am was founded, pouring house beers in a leafy garden and bar. It mixes a bit of aviation history with a relaxed happy-hour scene. Best for an easygoing drink under the trees with a sense of place.

A beloved nonprofit art-house cinema showing independent and foreign films in comfortable theaters with a real bar in the lobby. It's a civilized, air-conditioned alternative to another night on Duval. Best for a rainy evening or a film-lover's break from the heat.

A small historic aquarium on Mallory Square, open since the 1930s, with touch tanks, a shark feeding, and local reef species in an open-air setting. It's modest but hands-on and easy with kids. Best for a short family stop before the sunset celebration next door.

A grand red-brick Romanesque former custom house holding the island's art and history collections, from shipwreck-era paintings to Conch culture exhibits. It's the most substantial museum in town and often overlooked. Best for a cultured hour with a wide view of the island's layered past.

The original Sloppy Joe's location, a dim, story-soaked dive hung with bras and business cards where a tree grows through the bar and live music plays nightly. It's the locals' antidote to the polished tourist bars up the street. Best for a late, atmospheric drink with genuine Key West grit.

The Spanish-colonial house where Hemingway wrote through the 1930s, now a museum still run around the descendants of his polydactyl cats. The studio above the carriage house and the gardens are the draw, along with the dozens of six-toed cats lounging on the furniture. Best for a first-morning dose of the island's literary myth before the streets fill.

The painted concrete buoy marking the southernmost spot in the continental US, 90 miles from Cuba and one of the most photographed objects in Florida. The photo is the entire experience, and the line for it can be long. Best caught early or at dusk when the queue thins.

A pre-Civil War fort holding the largest cache of Civil War armament anywhere, fronted by what locals call the island's best beach. The combination of history, shade, and clear snorkeling water makes it the rare attraction that fills a whole afternoon. Best for swimmers who want fewer crowds than the Duval-end beaches.

The waterfront plaza that throws a nightly sunset celebration of buskers, fire-eaters, and food carts as the sun drops behind the harbor. It's touristy but genuinely fun, and even locals admit the sunset earns the crowd. Best for an early-evening wander an hour before the sun actually sets.

The 1890 naval quarters that became Truman's winter retreat and a working presidential office, preserved down to the poker table and period furniture. The guided tour is a tight, genuinely interesting slice of mid-century history. Best for a shaded hour of substance between beach and bar.

An 1848 lighthouse you can climb for one of the only elevated views on this famously flat island, with a small keeper's museum at the base. The 88-step climb pays off with a panorama over Old Town's tin roofs. Best paired with the Hemingway house directly across the street.

A 19-acre above-ground cemetery in the heart of Old Town, famous for its wry epitaphs and the tangle of Cuban, Bahamian, and Conch family histories packed into raised tombs. The most-quoted headstone reads 'I told you I was sick.' Best for a quiet, offbeat wander away from Duval's noise.

The historically Afro-Bahamian neighborhood just off Duval, with pastel conch houses, roaming chickens, and a slower pace than the tourist strip. Petronia Street is its spine, lined with the kind of cafes and bars locals actually frequent. Best for an unhurried walk that shows the island's other, quieter half.