With more than 500 years of history packed into a two-mile wide island famous for its shimmering teal waters, fresh sea-food, dazzling nightlife, and anything-goes bonhomie, Key West has many layers. Put yourself on relaxed island time as soon as you arrive and don’t try to see it all in one visit. There are, however, a few to do’s that should probably be on your list: attend a drag show, eat fresh seafood, and go the way of the island’s free-roaming chickens and ditch your car. Mixed-use neighborhoods are crowded with residences, bars, historical and architectural landmarks, and restaurants and shops. Some have little signage or appear in improbable locations. Throughout the historic Old Town district that extends from White Street to the ocean, bicycling and walking the streets and alleys is the best way to uncover the island’s delights. There is something for everyone in Key West and, as one of the town’s mottos suggests, “Everyone is welcome.”
3 p.m. Harbor Walk
If you took the Key West Express you’ll disembark at the start of the Harbor Walk and Seaport (keywestseaport.com) on Grinnell Street. Stroll along the waterfront and marina to where it ends at Front Street. It’s packed with commercial fisherman as well as fishing guides, tour operators and charter boats where you can book an array of ocean-going adventures and sports. A local’s favorite, Schooner Wharf Bar (202 William Street; 305-292-3302; schoonerwharf.com), will cook your fresh catch for you. It’s also known for having one of the best fresh mahi-mahi sandwiches in town (ask for it blackened).
5 p.m. Dinner and a movie
After you’re settled in at your accommodations for the night, head over to D.J.’s Clam Shack at the heart of the human parade (629 Duval Street; 305-294-0102; djsclamshack.com). If possible, grab one of the stools out front so you can people watch while you eat. Against your better judgement, make an unholy acceptation to the fresh, local seafood rule by ordering D.J.’s insanely satisfying Maine lobster roll and a sangria.
After dinner meander up Duval a block and dip a toe into the island’s pervasive artistic tendencies at Key West Gallery (601 Duval; 305-292-9339; keywestartgalleries.com).
Two more blocks up and just around the corner you’ll find Tropic Cinema (416 Eaton Street; 305-295-9493; tropiccinema.com) with a life-size statue of Marilyn Monroe out front. Call or check the website for showtimes around 7 p.m. or later as well as special screenings and events. This three-screen, art-deco movie theatre shows major Hollywood as well as indie, classic, and foreign films. It was restored by the Key West Film Society and opened for its first season in 1999.
9 p.m. Spooky nightcap
After the film, walk another block up to The Porch (429 Caroline; 305- 517-6358; theporchkw.com), known for its excellent selection of bohemian craft beer. It opened in 2010 in a 19th Century Victorian mansion that is on the National Register of Historic Places. Located on the corner of Duval and Caroline, it’s easy to miss from the street, set back behind a façade of tropical foliage. Try one of the 18 beers on tap or 50 by the bottle. Take your time (The Porch is open until 4 a.m.) and look around for the ghost of Dr. Joseph Yates Porter, a physician who once owned the place and died here. He’s said to be a friendly spirit.
8 a.m. Hit the beach
Start the day off right with some very chill Yoga on the Beach. It’s held from 8:15 to 9:45 a.m. at Fort Zachary Taylor State Park at the tip of Key West (601 Howard England Way; 305- 296-7352; yogaonbeach.com). There’s an $18 drop-in fee that includes a yoga mat and blanket. It’s a traditional Hatha class for all skill levels lead by Massachusetts yoga instructors Nancy Curran and Don Bartolone. After yoga take a dip, go snorkeling (rent gear at the concession area), or take a nature trail to check out an old Civil War-era fort.
11 a.m. Brunch
Pack for a picnic on the beach, stop by Fort Taylor Park’s Cayo Hueso Café or — better yet — make your way north up Petronia Street about four blocks and dine al fresco at Blue Heaven (729 Thomas Street; 305-296-8666; blueheavenkw.com). Breakfast is served until 2 p.m. and lunch starts at noon. The menu includes an array of a la carte pancakes, eggs benedict with lime hollandaise, and key west pink shrimp and grits. Enjoy a slice of key lime pie for dessert and admire the cats and roosters that wander the property.
12:30 p.m. Get the lay of the land
It’s a roughly 30-minute drive up to Sugarloaf Airport. There, certified instructors jump in tandem with you out of “a perfectly good airplane.” Even though you’re falling two miles above the ground at up to 130 miles per hour, it feels like you’re floating until you land about seven minutes later. You’ll see the keys stretched out to Key West to the south and north to Marathon. Make reservations a day in advance (MM17 US Highway 1, Sugarloaf Key; 305-745-4386; keywestskydiving.com). Flights go up on the hour every day from 9 a.m. through the early afternoon ($265 on a card or $245 in cash per person).
2 p.m. Pay your respects to the dead
Take a walk about town or if your feet are tired rent a bicycle at Red Doors Bicycle Rental (822 Caroline Street; 305-296-6628; bikemanbikerentalkeywest.com).
First, cruise over to the city cemetery at the northeast end of Old Town. As many as 100,000 people are buried here in plots on this 19-acre final resting place, more than three times the island’s population. Key West Cemetery (701 Passover Lane; 305-292-8177; friendsofthekeywestcemetary.com) was established in 1847 — placed at the city’s highest elevation with many of the graves above ground to protect gravesites from flooding. There are separate sections where Catholic and Jewish people have been buried, and a memorial for those who died in the 1868 Cuban revolution. You may also find some witty epitaphs. “See I told you I was sick” reads one stone.
4 p.m. Mansions, museums and shopping
From the cemetery take Margaret Street back to Caroline. Head south down Caroline toward Duval and check out the old world mansions such Amsterdam’s Curry Mansion Inn, an 1869 residence and now a bed and breakfast, whose architecture is a distinct island blend of Bahamian and Victorian sensibilities (511 Caroline Street; 305-294-5349; currymansion.com).
Near the end of Caroline make a right and cut over to Front Street. Here you’ll find yourself in a tangle of streets, a nexus of historic buildings, museums, shopping and dining. Wander like the chickens to the Key West Museum of Art & History (301 Front Street; 305-294-1241; keywestartcenter.com) or explore maritime heritage at the Shipwreck Museum (1 Whitehead Street; 305-292-8990; keywestshipwreck.com).
Visit Clinton Square Market set in a 19th Century building once used as a Navy coal depot (291 Front Street; clintonsquaremarket.com). You’ll find two stories worth of shops such as Island Cigar Factor and The Blue Cat and Red Dog Too (a boutique for pets).
6 p.m. Sunset at Mallory Square
When the sun gets low in the sky make your way to the waters edge at Mallory Square plaza (400 Wall Street; malloryssquare.com), where crowds and performers gather nightly to celebrate sunset. Magicians, clowns, fire juggling acrobats, and psychics show up a few hours before the day ends in the blaze of the dropping sun. Take your pick of restaurants or food vendors near the square for dinner.
Next to the plaza, The Sunset Pier at the beginning of Duval Street (0 Duval Street; 305-296-7701; oceankey.com), is a casual, picturesque place to relax on the water and fortify yourself for Key West nightlife with a plate of pork empanadas, fresh oysters and seafood Cioppino.
9 p.m. — 4 a.m. Nightlife and a drag show
Join the human parade on Duval Street in all its gaudy, racy, neon-streaked, low-brow, Saturday night glory. You are best left to your own devices walking up and down this hustling, bustling street enjoying a drink here or there, popping into art galleries or shopping for a delightfully obscene t-shirt. As one inn keeper advised, “Just follow the music.”
There are a few landmarks on Duval to point out. Sloppy Joe’s Bar (201 Duval) was Ernest Hemingway’s favorite drinking hole. About a block down you’ll find the Bull & Whistle Bar; the rooftop bar here is the “clothing optional” Garden of Eden.
It’s only about a mile from one end of the island to the other on Duval. But if you find yourself listing to port, flag down one of the pedicabs, a guy on a bicycle with a passenger car in tow.
Finally, attend a drag show. You’ll find spectacular-looking queens at the 801 Bourbon Bar (801 Duval) mingling with the customers downstairs or strutting their stuff out on the street to attract passers-by. Buy a $10 ticket for the 9 p.m. or the 11 p.m. show in the 801 Cabaret upstairs, and make sure you also have plenty of $1 bills to tip the queens. The songs are rocking, the costumes eye popping, and the humor full of double entendres.
Noon. Comfort food and coffee.
Sleep as late as possible and treat yourself to Glazed Donuts (420 Eaton Street; 305-294-9142; glazeddonuts.com) whose motto is “everything in moderation, including moderation.” The coffee is strong, organic, fair-trade and fresh brewed. Or try a fresh-squeezed mimosa for some hair of the dog. The scratch-made donuts are fresh each day and full of seasonal and local island flavors such as blood orange marmalade, lemon pistachio and mango hibiscus. The operation is overseen by Megan Pidgeon, an accomplished graduate of The Culinary Institute of America’s Baking and Pastry Program. If you’re an early riser the hours are 7 a.m. to 3 p.m.
3 p.m. One last good look around.
Climb aboard the Conch Tour Train (303 Front Street; 305-294-5161; conchtourtrain.com) for one last good long look at the island on a pleasingly kitschy 90-minute tour through local history. Tickets are $29. This will tie together the places you’ve seen, give you some perspective, and let whatever’s left of your hangover dissipate.
There are accommodations in Key West’s Old Town district ranging from a cheap youth hostel to elegant bed and breakfasts. Room prices during season range from about $200 to $300 per night and up. Call or check rates on websites.
Olivia by Duval offers a number of different guest rooms all near the action (main office on 913 Duval Street; 305-296-5169; oliviabyduval.com). The Wicker Guesthouse includes three homes with 11 rooms, a front porch and heated pool. Guests can use the bicycles on property. There is also a duplex and smaller rooms including for one.
Le Concha Hotel & Spa is the tallest building in Key West at six stories, and also where Tennessee Williams came to rewrite “A Streetcar Named Desire” in 1947 (430 Duval Street; 305-296-2991; laconchakeywest.com).