159 miles SW of Miami
There are two schools of thought on Key West -- one is that it has become way too commercial, and the other is that it's still a place where you don't have to worry about being prim, proper, or even well-groomed. I think it's a bizarre fusion of both -- a fascinating look at small-town America where people truly live by the (off) beat of their own drum, albeit one with a Coach outlet, Banana Republic, Starbucks, and, most recently, a handful of multimillion-dollar condo developments, thrown in to bring you back to reality. The locals, or "conchs" (pronounced conks), and the developers here have been at odds for years. This once low-key island has been thoroughly commercialized -- there's a Hard Rock Cafe smack in the middle of Duval Street, and thousands of cruise-ship passengers descend on Mallory Square each day. It's definitely not the seedy town Hemingway and his cronies once called their own. Or is it?
Laid-back Key West still exists, but it's now found in different places: the backyard of a popular guesthouse, for example, or an art gallery, a secret garden, a clothing-optional bar, or the hip hangouts of Bahama Village. Fortunately, there are plenty of these, and Key West's greatest historical charm is found just off the beaten path. Don't be afraid to explore these residential areas, as conchs are notoriously friendly. In fact, exploring the side streets always seems to yield a new discovery. Of course, there are always the calm waters of the Atlantic and the Gulf of Mexico all around.
The heart of town offers party people a good time -- that is, if your idea of a good time is the smell of stale beer, loud music, and hardly shy revelers. Here you'll find good restaurants, fun bars, live music, rickshaw rides, and lots of shopping. In recent years, Duval Street has actually struggled to maintain its raw, raucous flavor, as a spate of newer, swankier spots have opened in the spaces that formerly housed raunchy T-shirt and souvenir shops. Key West is still very gay-centric, except during Spring Break. Same-sex couples that walk hand in hand are the norm here; if you're not open-minded and prefer to avoid this scene, look for the ubiquitous rainbow flag hanging outside gay establishments and you'll know what to expect. For the most part, however, the scene is extremely mixed and colorful. If partying isn't your thing, then avoid Duval Street -- the Bourbon Street of South Florida -- at all costs. Instead, take in the scenery at a dockside bar or ocean-side Jacuzzi. Whatever you do, don't bother with a watch or tie -- this is the home of the perennial vacation.
When entering Key West, stay in the far-right lane onto North Roosevelt Boulevard, which becomes Truman Avenue in Old Town. Continue for a few blocks and you'll find yourself on Duval Street, in the heart of the city. If you stay to the left, you'll also reach the city center after passing the airport and the remnants of historic houseboat row, where a motley collection of boats once made up one of Key West's most interesting neighborhoods.
Several regional airlines fly nonstop (about 55 min.) from Miami to Key West. American Eagle (tel. 800/433-7300), Continental (tel. 800/525-0280), Delta (tel. 800/221-1212), and US Airways Express (tel. 800/428-4322) land at the recently expanded Key West International Airport, South Roosevelt Boulevard (tel. 305/296-5439), on the southeastern corner of the island.
Greyhound (tel. 800/231-2222; www.greyhound.com) has buses leaving Miami for Key West every day for about $35 to $48 one-way and $69 to $93 round-trip. Seats fill up in season, so come early. The ride takes about 4 1/2 hours.
You can also get to Key West from Fort Myers or Marco Island via the Key West Express (tel. 866/KW-FERRY [593-3779]; www.seakeywest.com), a 155-foot-long catamaran that travels to Key West at 40 mph. The Big Cat features two enclosed cabins, sun seated deck, observation deck, satellite TV, and full galley and bar. Prices range from $85 one-way and $140 round-trip per person.
Old Town Key West has limited parking, narrow streets, and congested traffic, so driving is more of a pain than a convenience. Unless you're staying in one of the more remote accommodations, consider trading in your car for a bicycle. The island is small and flat as a board, which makes it easy to negotiate, especially away from the crowded downtown area. Many tourists choose to cruise by moped, an option that can make navigating the streets risky, especially because there are no helmet laws in Key West. Hundreds of visitors are seriously injured each year, so be careful and spend the extra few bucks to rent a helmet.
Rates for simple one-speed cruisers start at about $10 per day. Mopeds start at about $20 for 2 hours, $35 per day, and $100 per week. The best shops include the Bicycle Center, 523 Truman Ave. (tel. 305/294-4556); the Moped Hospital, 601 Truman Ave. (tel. 305/296-3344); and Tropical Bicycles & Scooter Rentals, 1300 Duval St. (tel. 305/294-8136). The Bike Shop, 1110 Truman Ave. (tel. 305/294-1073; www.thebikeshopkeywest.com), rents cruisers for $12 per day, $60 per week; a $150 deposit is required.
Parking -- Parking in Key West's Old Town is particularly limited, but there is a well-placed municipal parking lot at Simonton and Angela streets, just behind the firehouse and police station. If you've brought a car, you may want to stash it here while you enjoy the very walkable downtown part of Key West.
The Key West Chamber of Commerce, 402 Wall St., Key West, FL 33040 (tel. 800/527-8539 or 305/294-2587; www.keywestchamber.com), provides both general and specialized information. The lobby is open daily from 8:30am to 6pm; phones are answered from 8am to 8pm. The Key West Visitor Center (tel. 800/LAST-KEY [527-8539]) is the area's best for information on accommodations, goings-on, and restaurants; it's open Monday through Friday from 8am to 5:30pm, Saturday and Sunday from 8:30am to 5pm. Gay travelers may want to call the Key West Business Guild (tel. 305/294-4603), which represents more than 50 guesthouses and B&Bs, as well as many other gay-owned businesses. (Ask for its color brochure.)
While you're in one of the above offices, be sure to pick up a free copy of Sharon Wells' Walking & Biking Guide to Historic Key West. Though I still couldn't find all the spots I wanted to in the Key West Cemetery while using the guide, it was helpful for historic descriptions throughout town. Sharon Wells also leads guided walking tours around the island. For information, call her at tel. 305/294-8380 or go to www.seekeywest.com.
A mere 2*4-mile island, Key West is simple to navigate, even though there's no real order to the arrangement of streets and avenues. As you enter town on U.S. 1 (Roosevelt Blvd.), you will see most of the moderate chain hotels and fast-food restaurants. The better restaurants, shops, and outfitters are crammed onto Duval Street, the main thoroughfare of Key West's Old Town. On surrounding streets, many inns and lodges are set in picturesque Victorian/Bahamian homes. On the southern side of the island are the coral-beach area and some of the larger resort hotels.
The area called Bahama Village is the furthest thing from a tourist trap, but can be a bit spotty at night if you aren't familiar with the area. With several newly opened, trendy restaurants and guesthouses, this hippie-ish neighborhood, complete with street-roaming chickens and cats, is the roughest and most urban you'll find in the Keys. You might see a few drug deals happening on street corners, but they're nothing to be overly concerned about: It looks worse than it is, and resident business owners tend to keep a vigilant eye on the neighborhood. The area is actually quite funky and should be a welcome diversion from the Duvalian mainstream.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.