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By Lena Katz

It’s sunset in Key West, and as usual, at least three people in Mallory Square are playing with fire. One’s juggling it, one’s dancing with it, and the third seems to be ready to eat it. A few yards away, a man in a straitjacket and chains hangs upside down above an excited crowd.

Mallory Square, Sunset Celebration. Photo by Gary Sibley

Mallory Square, Sunset Celebration. Photo by Gary Sibley

Oblivious to the street theater, German tourists push forward to the seawall, straining to snap photos of the sunset over the ocean. A cruise ship looms large on the horizon, with a few sailboats floating serenely in the mist. Even though autumn’s officially started, this town is eternally on a beach holiday—as are all of the Florida Keys. It’s one of several island clusters that offer Midwest and East Coast residents an easy golf getaway, fishing trip, spa weekend…not quite a full vacation, but enough to tide you over till the holidays.

The Florida Keys are just a half-hour jaunt from Miami, but many of its return guests are from Indianapolis and Ohio, Chicago and Boston…chilly cities that excel at business, but have forgotten how to relax. With mile after mile of peaceful, barely trafficked islands connected by narrow bridges and populated mostly by birds, the Keys literally offers a journey into to serenity.

The uppermost island, Key Largo, is the busiest except for Key West. Dozens of fishing expeditions and dive boats go in and out daily, the fishing boats in search of tarpon and bonefish (catch-and-release only), and the dive boats cruising to the offshore coral reef.  It’s hard to choose between the many boat operators, but locals recommend Florida Keys Outfitters for fishing. Atlantis Dive Center is a hugely popular snorkel/dive boat operator—founder Spencer Slate’s shtick involves feeding moray eels chunks of fish from his mouth (he used to do barracuda till one of the fish chomped his mask off).

There are hotels all over Key Largo:  Pines and Palms, offering breezy and spacious cottage-style accommodations mere footsteps from a private beach; the deluxe self-contained Key Largo Bay Marriott; and the ever-reliable Ramada.  Villa-style Dove Creek Lodge is great for water enthusiasts, especially fishermen—it has a marina on-property and runs motorized and non-motor boat expeditions into local waters for guests’ choice of activities.

Baby turtle in Key Largo Wildlife Preserve

Baby turtle in Key Largo Wildlife Preserve

Most of the Keys are obscure, sparsely populated, and difficult to know by name. While a few little galleries, wildlife preserves and fine dining restaurants can be found on picturesque Islamorada, the middle Keys directly south of it are simply grouped under the district Marathon. And indeed, it is a marathon, traversing the everlasting narrow bridge, skimming over islands so narrow you can see water on either side. These islands are too small to even hold towns; a few have “neighborhoods” comprised of clusters of houses. Every resident has a boat out back of their house, and the few resorts are spread-out, self-contained, very tranquil and very upscale with a Southern plantation feel. Hawk’s Cay is great for families, offering everything from sailing to spa.  Tranquility Bay boasts the biggest pool in the region, as well as a small but picturesque beach where the water’s so still and warm, it feels like a wading pool.

Pines and Palms Resort, Key Largo

Pines and Palms Resort, Key Largo

When you get to Key West hang onto your hat. Even if you’re forewarned that this island is very different from its neighbors, nothing can prepare you for the spectacle that assails you upon entering Old Town Key West. Suddenly the action-ometer spikes from zero to almost 100, and you’re agog wondering, “Where did all this come from?”  Crowds of people meander along Duval Street, chugging beers at 1PM and buying up $5 tee-shirts. The seafood restaurants in the marina can seat hundreds of people, yet they’re invariably filled up by 6PM on a weekday, in low season. The bars are packed till 2AM, the trolleys are standing room only, and the parties are legendary. (The biggest is actually coming up—Fantasy Fest kicks off October 23rd this year and runs through November 1st.)

In spite of how utterly chaotic it can be, Key West somehow steers clear of being a tourist trap. It’s colorful and offbeat, populated by an interesting combination of ex-hippies, possible former smugglers, wealthy East Coast transplants, professional artists and lifelong seafarers (sailors, fishermen, Navy contractors). Old Town has hundreds of preserved historic homes and inns that look unnervingly alike from outside. Its attractions, however, are diverse, ranging from the Pirate Soul Museum to the Ernest Hemingway House (now home to between 40-50 six-toed cats) to the legendary 801 Cabaret drag club (Sushi, the star performer, appears on CNN’s New Year’s Eve countdown every year). Offshore activities are just as numerous—you can jet ski, take a glass bottom boat ride, dive for sunken treasure, or take a ferry to Dry Tortugas National Park. The Sunset Celebration at Mallory Square occurs nightly, weather permitting, and immediately afterward the nightlife scene kicks into high gear.

Since you have to sleep sometime, there are plenty of hotels in Key West:the Ocean Key, the Pier House, and a new Westin Key Resort and Marina right next to Mallory Square. However, insiders say that the truly authentic guest experience can only be had at a historic B&B. Charming, reasonably priced picks include Island City House and Orchid Key Inn. Duval House and Dewey House are slightly more expensive, and better for couples.

Stay tuned as we bring you even more island getaways—no passport required, and right in your backyard.  There’s a lot of weekends between now and the holidays, and we at Orbitz figure you might as well make the most of them.

Related Resources

Lena Katz is the author of SUN: California and SIP: California, part of the Travel Temptations series published by Globe Pequot Press.

Tagged: Florida

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