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.