Key West is a funky, fabulous cruise destination. While first-timers should do the tourist thing -- get their bearings on a Conch Train tour, visit the Hemingway Home and museum, have a drink at one of Hemingway's favorite bars, Sloppy Joe's, enjoy a "Floribbean" lunch at Mangoes and watch the daily sunset celebration at Mallory Square -- next-timers can venture off to explore an insider's view of the Conch Republic.
The Southernmost Point of the continental U.S., where Route 1 dials down to Mile Zero, offers an astounding number of sights, hot spots and only-in-Key West attractions. Here are 10 of our favorite things that never get old, no matter how often we visit.
Banana Café (1215 Duval, 305-294-7227) is a sweet French bistro known for its crepes and wine menu. They serve "Breakfast/Lunch" daily from 8 a.m. to 3 p.m. and dinner from 6 p.m. Monday through Sunday (Tuesday through Saturday in the summer). It's also in the quieter, refined portion of Duval Street, next to art galleries and specialty shops. The two-story building, two blocks from the Atlantic Ocean, is the birthplace of famous Key West folk artist Mario Sanchez.
Key Westers love their ice cream and often head to Flamingo Crossing (1105 Duval, 305-296-6124), where local flavors include Mango, Sour Sop/Guanabana, Key Lime and Cuban Coffee. Gelatos include a few liquor-infused treats like Rum Runner and Chocolate Amaretto, and frozen yogurt and non-dairy sorbets are also on the menu. Enjoy your treat outside in the garden or as you stroll the quieter side of upper Duval. Fun fact: The building next door, 1107 Duval Street, was originally a home built from salvaged materials from a World War I blimp hangar.
Garden of Eden (224 Duval 305-296-4565), above the Bull & Whistle Bar, is Key West's clothing-optional rooftop bar. Yes, we mean naked, but the bartender will give you a towel upon request. Venture up the stairs to the garden at the building's top, and hope there are people there worth seeing in the buff. Be aware that photos are not allowed, and the policy is strictly enforced. The bar opens daily at 10 a.m. If the setting doesn't suit your tastes, the Bull is always right below.
There is a long list of galleries in the tiny arts mecca of Key West, but, for something different, check out Hands On (1206 Duval, 305-296-7399), where all of the art is ready to wear. The shop, inside one of the island's iconic "Conch" houses, sells distinctive wearable art in clothing, accessories and jewelry.
It stands out as the towering, red-brick historic building on the waterfront. And if you venture inside the beautifully restored Custom House, built in 1891, you'll also find the Key West Museum of Art & History (281 Front Street, 305-295-6616), with its two floors of exhibitions that stitch together 200 years of history, art, people and events. Collections include Mario Sanchez's vivid, painted woodcarvings of his childhood memories, Henry Flagler's Overseas Railroad and Hemingway's life and legacy in Key West. There's a small admission fee for both children and adults.
When Ernest Hemingway first came to Key West in 1928, it was to buy a car. He stayed at what is now known as Casa Antigua (314 Simonton Street at Caroline, 305-292-9955), one of the island's first hotels that catered to folks who'd traveled to the island to buy a car -- and wound up waiting for it. It had a Ford dealership on the ground floor. Hemingway and his wife Pauline ended up staying two weeks and falling in love with the seaport town; the author finished "A Farewell to Arms" inside one of the rooms. To get inside, you have to enter the gift shop known as Pelican Poop, where you can tour the property for a small fee. Casa Antigua is also where the awards are presented in the annual Lorian Hemingway Short Story competition, named after and directed by Hemingway's granddaughter.
When Conchs -- islandese for Key West natives -- want a quick lunch, they stop by 5 Brothers Grocery and Sandwich Shop (930 Southard Street, 305-296-5205). Try a Cuban Mix: cold cuts of sweet ham on grilled bread with pickles with a side of Yuka fries. The store is in the residential neighborhood of Old Town, but it's worth every step off the beaten path. Buy a sandwich or a Cafe con Leche, strong espresso coffee with steamed milk, and sit outside on one of the benches to watch the real Key West saunter by.
Sure, Duval Street is full of bars, but if you want to drink like a local, go to the Green Parrot (601 Whitehead Street, 305-294-6133). Just a few blocks away from Duval, this open-air tropical saloon opened in 1890 and remains a Key West icon where everyone is welcomed, as long as they adhere to the bar's official motto: "No Snivelling." The jukebox is a treasure chest, featuring bluesmen like B.B. King and John Lee Hooker. There's live music on weekends and some weeknights, and there's never a cover charge. It's open daily from 10 a.m. to 4 a.m. Happy hour is daily from 4 p.m. to 7 p.m.
This tropical island takes pride in natural beauty, and nowhere is that more evident than inside the Key West Butterfly and Nature Conservatory (1316 Duval St., 305- 296-2988). Visit hundreds of the breathtaking and winged creatures, along with exotic birds, cascading waterfalls and trees, all under a climate-controlled glass-enclosed habitat. The newest residents are a pair of young flamingos. It's open 9 a.m. to 5 p.m. daily. There's a small admission fee for children and adults.
One of Key West's most affordable eateries is the Cuban Coffee Queen (284 Margaret Street, 305-294-7787), where breakfast and lunch are served daily from 6:30 a.m.to sunset, right in the heart of the island's historic seaport. Try the Mojo roasted pork on a sandwich named after Jose Marti or a classic Cuban Mix. They offer a host of coffee selections, from traditional Cafe con Leche to Bucci (espresso shots) and iced coffees. They encourage you to dip their Pan Cubano -- warm, buttered, pressed Cuban bread -- into the brew. The little building is known for its "Greetings from Key West" postcard mural that takes up one wall.
--Updated by Gwen Filosa, Cruise Critic contributor