Florida Keys

Watch the sun sink over plates of Caribbean conch and fresh catch from the back deck of a pink Victorian.

Fresh fish sandwiches, key lime coladas, sunsets.

Beloved education center and nonprofit for turtle rescue, rehab and release.

Tasting fresh, from fresh catch to passionfruit sorbet.

Fish and grits, T.J. salsa (also sold by jug) and key lime pies or shakes.

Bahama Village curries, rotis, Trinidadian doubles.

Local favorite going beyond fritters—such as flash-fried conch with ponzu and wasabi.

Buffett sand about it. Hemingway ref'ed boxing where chicken strut. BBQ shrimp, cornbread.

Beloved Cuban sandwiches to-go from back counter of this grocery, since 1978.

Coffee roasting operation named for "Baby" Rodriguez, who once ran a cantina in the 1920s building.

Strip mall favorite run by Jersey expats.

Hidden gem bakery on Stock Island—coffee and key lime beignets.

Post up between the palms on the patio at this coffee shop and cafe across from the Hemingway House.

Pitstop for coffee, Manny and Isa's key lime pie. Halfway between Miami and Key West.

Walk-up window at Cuban cafe draws locals for cafe con leche and guava pastry.

Espresso and fresh croissant in a former church built in 1890, rebuilt after 1935 hurricane.

A charter fishing trip or kayak rental with your latte? Book 'em at this pink-painted, drive-thru coffee hut.

Laundromat in back, Cuban coffees up front. Sandwiches, picadillo, ropa vieja from walk-up window.

"Any given day, it's a dive bar or the cultural center of the universe." -a local

Magical courtyard, twinkling lights in trees, live music.

A favorite watering hole since the '80s. Treasure hunter Mel Fisher was a fan.

Waterfront tiki bar where the bar stools sit on sand. Live music.

From general store (and brothel) to beloved bar and restaurant.

Cold beer and hogfish tacos under thatched shade.

Sip a Pineapple Express (pineapple rum, charred fresh pineapple, coconut cream) looking out on the Gulf.

If-walls-could-talk bar in a former hotel room space at the Pier House Hotel. Hot dogs gratis.

French colonial residence of Hemingway and Pauline Pfeiffer in 1930s. See where he wrote works like, "The Snows of Kilimanjaro."

Chock full of artifacts (diving helmets from more than 20 countries, antique diving suits) and history, included related topics like sponging.

Photographs, first edition plays and typewriter used by the author during his 30 years in Key West.

Museum, library and gallery founded in 1871 by Cuban exiles.

Neon-lit indie film house and gathering space for cultural events.

Treasure box of Florida history inside pink stucco walls. Ace place to meet the real-life characters in Key West's story.

Modern hub for the arts in a 1950s Miami deco building. Music, theatrical performances, visual art, lectures and residencies.

Exhibits about Calusa and the Tequesta tribes, pirates and wreckers, and history of Overseas Railway.

Built in 1891 as the island's customs office, postal service, courthouse. Now holds artifacts, lectures, paintings by Tennessee Williams.

Science activities, dock-to-dish dining, respected dive shop partnership.

Arrive to serenity by boat or seaplane. No TVs, phones taboo.

Seaside Victorian, heckuva past. Tennessee Williams on celeb shortlist.

Book a night (and a slip) at this chic but lively marina hotel. Shuttle to Old Town.

One of five Kimpton Hotel locations—this one tucked into gardens near Key West Lighthouse.

Railroad relic of 1920s. Winter home of poet Wallace Stevens.

Fish, golf, snorkel. Camp Cheeca for kids, with eco-minded fun.

19th-century seafoam-green conch house. Tranquil pools, elegant restaurant.

Cluster of seven remote islands with Civil War prison and fort. Coral reef, camping, bird stopover.

Rugged seascape sprouting palms. Fort, circa 1866, punctuates dramatic landscape.

Tranquil hideaway brimming with orchids, butterflies, aromatic native buds. View of turquoise sea.

Hike hardwood hammock to Florida Bay overlook in 1.5 miles.

Nearly 3,000 square nautical miles of coastal and ocean ecosystem with fish, coral, birds.

Boats slow-roll through mangroves to Molasses Reef as egrets stand watch. Snorkel, dive or kayak.

Wind through shade and quiet (except for warbler song), past coral fossils, wild cotton, mahogany mistletoe.

Snorkel over seagrass near old rail bridge. Stargazing, camping too.

Fine art, jewelry, salts—all local.

Front porch store for local designs and studio space of artist Billy Kearins.

Chic island styles, accessories, scents and gifts.

Coins, bracelets and other rare relics from wrecks.

Since 1926, via Cuban cigar maker turned grocer.

Boho decor, succulents suspended in macrame, hand-crafted jewelry.

Lovely gifts from stationary to cookbooks and scents.

Respected fly-fishing couple's outpost for rods, flies, lessons.

Bookshop at Studios of Key West, founded and run by beloved author Judy Blume.