Party town in paradise |

Party town in paradise

Lauren Glendenning
Vail CO Colorado

KEY WEST, Fla. – After three days in Islamorada kicking back on a boat, fishing and relaxing on a private beach, it’s now time to shift gears for the island of Key West.

Key West is a place that exudes that Florida Keys mentality of relaxation, but this place is full of color, character and history – more so than any other island in the Keys. It’s the southernmost point in the continental United States, just 90 miles from the island nation of Cuba and about 80 miles from Islamorada.

Duval Street, Key West’s main drag, is lined with restaurants, bars, shops and more bars. It’s swarming with pedestrians, many of whom are tourists sipping alcoholic beverages as they walk down the street and window shop.

It’s no surprise that Key West allows open containers throughout town – it feels like a lawless kind of place. That’s not to say there isn’t any order, but there’s an attitude about this place that makes it feel like just about anything goes. It’s easy to see how famous writers like former resident Ernest Hemingway have drawn so much inspiration from Key West.

Take the dessert-only restaurant called Better Than Sex, for example. Flamboyant waiters present a menu of desserts like the peanut butter perversion, the missionary crisp and the “between my red velvet sheets” cheesecake. They talk to you suggestively, and you better have a sense of humor in this place or you’ll be in for a shock.

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Better Than Sex walks a fine line between romantic and sleazy, but it’s just the kind of place you’d expect to find in the side of town that also houses two drag queen clubs and a few gay bars.

It’s a side of Key West that many travelers might not want to see, but don’t worry – you can easily avoid it and enjoy Key West for its luxury, too.

Luxury such as crystal blue waters and amazing snorkeling and scuba diving await, as do sunset sails and cruises available from a variety of tour operators. And the sport fishing, just like in Islamorada, is top notch.

Fury, one of the biggest tour operators, offers a sunset cruise, affectionately referred to as a booze cruise. If you want to feel like you’re out on the water for more than just cocktails, opt for the Rum and Reggae cruise which includes an hour of snorkeling before the bar opens. Then, watch a famous Key West sunset on the cruise back into the marina as you sip on rum punch and listen to soft reggae tunes.


Along Duval Street you’ll find everything from souvenir shops to fine dining restaurants to bars filled with people of all ages. There are frozen drinks galore – don’t miss the rum runner, a Key West favorite, at the Sunset Pier. And everyone wears flip-flops.

That’s another thing about Key West – you can leave your high heels back at the hotel room, or better yet, don’t bring any on the trip at all. This place is relaxed. There’s no need to fuss over what you’re wearing that night, and if you’re in Key West anytime in the summer you might as well forget about wearing any makeup, too, because you’ll just sweat it off the minute you walk outside.

They call this place Margaritaville, and when you spend some time here you’ll quickly realize why. Sure, it had a lot to do with Jimmy Buffet, a former resident of Key West, but you can see where he got the inspiration for those lyrics.

They also call Key West “The Conch Republic,” an identity that was first declared by Key West citizens in 1982 when the U.S. Border Patrol set up a roadblock and checkpoint between the Florida Keys and South Florida, the U.S. mainland.

The Conch Republic was a tongue-in-cheek secession in response to the roadblock, and you’ll see the phrase throughout Key West. On New Year’s Eve, a huge conch shell drops from atop one of the Duval Street bars, a Key West tradition that mimics the New York City ball drop.

While there’s plenty of fun to be had on Duval Street – and the fun often continues until 4 a.m., when many of the bars finally shut down for the night – the west end of Duval Street is home to the Ocean Key Resort and Spa, a tranquil, luxurious resort just steps from the Key West parties.

Some of the best people watching in town is from a balcony in one of the resort’s rooms. You can watch the street performers in Mallory Square, cruise ships entering and leaving the port, or even better, a Key West sunset.

Have a nice dinner at the resort’s Hot Tin Roof restaurant out on the patio, which overlooks the water, and kick back for the night or take a late-night swim in the resort’s oceanside pool for a side of Key West that is elegant and peaceful.

You can always bar-hop the next night – Duval Street never closes.

Community Editor Lauren Glendenning can be reached at 970-748-2983 or

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