Key West has two distinct halves. The eastern end of the island is largely residential and full of modern buildings, while the western end, or Old Town, is where most of the action is. Duval Street is the main north-south drag there and most of the hotels are located around it, making it easy to walk to most of the attractions, like the quirky cemetery, the Southernmost Point, and the Hemingway house. Make time to wander the backstreets shaded by leafy succulents and soak up the no-worries-man vibe that so defines Key West. Bahama Village, to the east of Duval, has remained largely unchanged despite the town's tourist surge. Here you'll find the old cigar makers' cottages as well as some of the local wildlife, including lizards scurrying across the street and prowling cockerels (it's against the law to slaughter them since they help control the scorpion population). Key West's beaches are mostly found along the southern rim of the island, including Fort Zachary Taylor Beach in the far west.
WHEN TO GO
It's always a perfect day in paradise from October to early June, when temperatures average a comfortable 80 degrees. Hurricane season runs June through November and is Key West's hottest, rainiest—and cheapest—season. Be advised: New Year's Eve and Fantasy Fest, a ten-day bacchanal costume bash at the end of October, bring a ton of tourists, sky-high room rates, and minimum-stay requirements. There are also many large fishing tournaments and boat races held throughout the year. Also keep in mind that when the big cruise ships are in port, the streets (particularly Duval) are swollen with the T-shirt-and-fanny-pack crowd. The good news is that they usually set sail by 5 pm and rarely dock here on Saturdays.
HOW TO GET THERE
Most visitors fly into Miami International Airport and drive four hours south on the dramatic and beautiful—if somewhat monotonous—Overseas Highway (U.S. 1), a 127-mile series of bridges and causeways. However, there are also regular puddle-jumper connections to Key West from Miami and Fort Lauderdale airports on American, Delta, Cape Air, and Continental (305-809-5200; www.monroecounty-fl.gov). From the Key West Airportwhich got a new terminal building in February 2009hop one of the pink cabs into Old Town for $7.50 per person. A smart option is to fly down one way (killer views on the low-altitude journey are a bonus) then mosey slowly back to the mainland by car along U.S. 1, or vice versa. It's also worth noting that traffic on Friday and Sunday afternoons can be epic.
Other options include the Keys Shuttle, a van that makes six runs daily from the Miami airport (305-289-9997; www.floridakeysshuttle.com). The drive takes about four hours and stops at various points around town. Ferry service is also available from Fort Myers and Marco Island, on Florida's west, coast via Key West Express; the ride takes three and a half hours (888-539-2628; www.keywestshuttle.com).
Don't try to drive in Old Town; parking is a nightmare. The best way to get around is by bicycle or scooter. Try renting from one of the three outfitters on Truman Avenue: the Bicycle Center (523 Truman Ave.; 305-294-8888; www.amscooterskeywest.com), Moped Hospital (601 Truman Ave.; 866-296-1625; www.mopedhospital.com), or the Bike Shop (1110 Truman Ave.; 305-294-1073). There are no helmet laws in Key West, but it's worth a few bucks to have extra protection. If you must drive, keep in mind that some—but only some—hotels have parking spaces for guests; otherwise, there are three municipal parking lots (www.keywestcity.com) and a private fee-paying lot on the water by the Westin hotel. Walking is always an excellent option, especially if you're staying in Old Town. Be sure to pick up a copy of Walking and Biking Guide to Historic Key West by historian Sharon Wells. She also leads tours around the city (305-294-8380; www.seekeywest.com).
Key West Chamber of Commerce
402 Wall Street
Tel: 305 294 2587
You can pick up leaflets and plenty of free maps here, though don't expect the staff to be overly knowledgeable.
Key West Business Guild
513 Truman Avenue
Tel: 305 294 4603
A superb resource for gay and lesbian travelers.
Author Joy Williams's guide book The Florida Keys is a fantastic literary-minded take on the area. The most recent update was published in 2003, so be aware that some of the info may be out of date.