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IT'S tough to slap an itinerary on Key West. The whole point of this two-by-four-mile island, after all, is to kick off your shoes and let it all hang out. But here's the rub: do Key West wrong and you might not relax. Witness lower Duval Street, that cacophony of sound, sunburn and daiquiris. (Hemingway used to drink there, but he might think twice today.) So where is the strange, laid-back island that everyone fell in love with? It's still there, if you know where to look. It's found biking through Old Town at dusk, when the porches light up and jasmine fills the air. Or kayaking across the quiet, teal-blue ocean, or catching an old-timer's tale, drifting across a lonely bar. Done right, Key West is still a place where time stands still.

Friday

5 p.m.
1) SLOW AND STEADY

Why begin your weekend by watching two turtles race? Because this is Key West, man, and you need to chill out. Oh, and there's beer. The Friday night turtle race at Turtle Kraals (231 Margaret Street, 305-294-2640; www.turtlekraals.com) is just the kind of maverick genius this town was built on. Grab a ticket from the bartender for the 6 p.m. race, and join the crowd as people pump their fists and hurl mock threats at a handful of box turtles inching their way down a shuffleboard table. Betting is free, and winners get a chance to vie for a cash prize. At sunset, head to the rooftop bar overlooking the Key West Bight for a cold draft and one of the sweetest views in town.

8 p.m.
2) NO JACKET REQUIRED

You don't need to dust the sand off your feet to eat right in this town. For the perfect fish sandwich, head to B.O.'s Fish Wagon (801 Caroline Street, 305-294-9272), a hopping little open-air shack that turns out fresh food with zero fuss, as well as great live music on Friday nights. The owner, Buddy Owen, is something of a local legend, having started his operation more than 25 years ago out of a little wagon on Duval Street. Last year, Bobby Flay and his Food Network camera crew paid a visit. And no wonder. Don't miss the cracked conch sandwich ($12), tiny strips of fried conch stuffed between fresh Cuban bread and shot with Key Lime mayo. Sounds simple, but no — heaven.

Saturday

10 a.m.
3) ROLLING MANGOES

How long does Lloyd's Tropical Bike Tour (305-294-1882; www.lloydstropicalbiketour.com) last? “In your mind,” Lloyd Mager likes to tell his customers, “forever.” If you only take one tour, make it this strange, awesome trip through the back streets of Key West. The Bronx-born, mango-obsessed Mr. Mager ducks in and out of private gardens (including his older brother's, much to his chagrin), hacking at coconuts with his machete, cracking jokes and spreading the local lore he has cultivated in his 35 years on the island. The stop at Nancy Forrester's Secret Garden, a stunning little rain forest with exotic parrots and an artist gallery, is worth the cost alone. The tour is $35 and lasts (in real time, anyway) two hours.

1 p.m.
4) A CUT OF THE CARIBBEAN

Skip the sit-down lunch and take a stroll down Petronia Street in the historic Bahama Village. Settled by black Bahamians in the 19th century, the neighborhood is a gentle mix of old and new charms, including a cluster of shops and some surprising food finds. Stock up on candles and Kiehl's at Bésame Mucho (315 Petronia Street, 305-294-1928), then cross the street to the Art of Baking by Henrietta (316 Petronia Street, 305-295-0505; www.henriettakeywest.com) for a piping hot café con leche and coconut strips — long, crunchy cookie-like pastries. Walk past the iconic Blue Heaven restaurant, and look for an unmarked lime-green market, Julian's Grocery (730 Emma Street, 305-292-1222). No one would guess it, but it sells an excellent conch ceviche ($8).

3 p.m.
5) CHICKEN RUN

People in this town don't kid when it comes to chickens. They're on the loose everywhere, and it's a battle — half the island is trying to save the little cluckers, the other half is endlessly annoyed. And then there are the kids stealing them for cockfights. Learn all about the Key West chicken wars at the Chicken Store (1229 Duval Street, 305-294-0070; www.thechickenstore.com), where you can hold a fuzzy baby chick, feed a rooster or buy a clever T-shirt. If the heart is swayed, you can even file for adoption.

4 p.m.
6) SEA OF OPTIONS

In a town not known for its beaches, Fort Zachary Taylor Historic State Park (tip of Southard Street, 305-292-6713; www.fortzacharytaylor.com) is a beauty, with wide stretches of sand and tranquil waters. If swimming sounds tame, these islanders like their watersports (a former mayor once water-skied to Cuba to make a political statement). You can rent a snorkel set ($10) or a two-person glass-bottom kayak ($20) from the concession area. Back on the beach, soak up the generous shade while you can; the state recently felled a row of pine trees, briefly displacing the chickens as the controversy du jour.

7 p.m.
7) ABOVE THE FRAY

If you have to bite on one tourist haunt, make it Mallory Square, where crowds gather to watch the sunset. This nightly hoopla down at the historic waterfront is loads of fun, even if it's difficult to see the dipping sun between the jugglers and tightrope walkers. If the crowds get too heavy, head to the Roof Top Café (308 Front Street, 305-294-2042; www.rooftopcafekeywest.com), where you can replace the ruckus with a bird's-eye view of the bustling street and a cold cocktail.

8:30 p.m.
8) NO RESERVATIONS

For a beach bum town, Key West takes its food very seriously. Ask a resident for dinner recommendations, and you'll be chatting for days. Problem is, most of them require reservations — and who feels like planning in paradise? Enter Café Med (425 Grinnell Street, 305-294-1117), a pretty little restaurant tucked so deep inside Old Town that there's rarely a wait. Try the excellent mushroom soufflé with truffle oil ($8.50), followed by a freshly seared yellowtail snapper ($28). Also under the radar is Prime 951 (951 Caroline Street, 305-296-4000), a sexy mahogany-lined steakhouse that serves fat tumblers of martinis.

11 p.m.
9) A SEAT OF ONE'S OWN

Contrary to popular belief, people in Key West are not drunk all the time. But let's just say it's late, and you have some catching up to do. Finnegan's Wake (320 Grinnell Street, 305-293-0222; www.keywestirish.com) is the kind of split-personality bar you dream about. Though it hugs a quiet corner of Old Town, inside you'll find live music and frothy $5 pints of Smithwick's. Out back is even better — a secluded backyard pub where you're almost guaranteed a seat while the band plays in the distance. If you're looking to hit a drag show — and the ever-popular Aqua (711 Duval Street, 305-294-0555; www.aquakeywest.com) is packed — check out the lively and less crowded cabaret at 801 Bourbon Bar (801 Duval Street, 305-296-1992; www.801bourbon.com).

Sunday

Noon
10) THE NEXT ISLAND OVER

The real Key West? It's not even on Key West proper anymore, but just over the Cow Key Channel Bridge, on the even tinier Stock Island. Follow Front Street past a row of old trailers, and you'll stumble upon a little miracle: the Hogfish Bar and Grill (6810 Front Street, 305-293-4041; www.hogfishbar.com), a big, clamoring seafood joint at a marina that is rumored to have been the headquarters for the Bay of Pigs operation. Grab a table by the water, and try a fresh hogfish sandwich ($12.95), loaded with Swiss, mushroom and onion. Soak up the afternoon sun, toss some bread at the passing fish, and don't rush home. Local investors plan to develop this area over the next 10 years — they figure that when Cuba opens up, Stock Island will be the next Key West.

The Basics

How best to get to the southernmost point in the United States? Several major airlines offer frequent connections through Miami and other Florida airports, with flights from New York starting at about $400. Many visitors choose to drive the scenic 155 miles from Miami.

A shiny new option is the Key West Express (866-593-3779, www.seakeywestexpress.com; $98 round trip), a four-hour ferry departing twice a day from the Miami Seaquarium. You won't need a car in Key West: most people walk or ride bikes.

In a sea of boutique hotels, the Gardens Hotel (526 Angela Street, 305-294-2661; www.gardenshotel.com) has 17 impeccable suites, spread across an acre of tropical gardens, that are steps from everything but as quiet as a country inn. Rates begin at $285 in high season.

The Mermaid & the Alligator (729 Truman Avenue, 800-773-1894; www.kwmermaid.com) has nine rooms in a Victorian-style mansion in the historic district. The Key Lime and Papaya rooms are a steal at $168 a night each.