Bar Hopping Like A Local In Key West Florida – 7 of the Best Bars in Key West

March 1, 2010 | By | Reply More
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Find the best bars and cafes secluded along quiet lanes and tucked into hidden gardens. While throngs of tourists swarm the main thoroughfares of Key West stopping in every garish bar blasting rock music and Buffet tunes, the locals weave their way through quiet side streets arriving at hidden garden cafes, neighborhood bistros and seaside bars that few tourists are lucky enough to discover.  These are the establishments full of charm and panache that can turn Key West visitors into Conch Republic devotes.  Clint and I went bar hopping with some locals a few weeks back, and I’m happy to share with you a few of the amazing and entertaining spots they introduced us to.

The Afterdeck At Louie’s Backyard
Each evening as hundreds of vacationers jam themselves into Mallory Square to watch the famous Key West sunset, a more discerning group gathers at Louie’s Backyard Restaurant at the Afterdeck Bar which sits right on the beach close to the Southernmost Point.  This is a bright and sunny open air spot to begin your evening with a seaside happy hour cocktail, enjoying the last sunny rays of the day.  The sun drops dramatically behind an adjacent pier pavilion.

Kelly’s Caribbean Bar, Grill & Brewery
Just up the street and around the corner at the junction of Whitehead Street and Caroline, you’ll find Kelly’s (owned by Kelly McGillis of Top Gun fame).  Walk into the deceptively small white bay front cottage and enter the historic former Pan Am sales office – turned chic bar.  (If at all possible claim your spot just before happy hour begins at 4:00 pm, as an enthusiastic crowd gathers quickly).  The hot wings fly all around cooled by the famed margaritas or one of their renowned home brews.  Step out back to take in the impressive garden restaurant lit by twinkling white lights.

The Gardens Hotel
Located just a block off Duval Street, (but a world away),  you’ll find the beguiling Gardens Hotel and its sensuous courtyard patio. While this tropical enclave is usually open for hotel guests only, the public is welcomed often for exhibits showcasing local artists.  We spent a very entertaining hour viewing a fashion show, sipping aperitifs, while a jazz band played on the porch – enchanting!!  The next time we return to Key West, we’ll definitely stay at this property – it’s a knock out!

Santiago’s Bodega
By now you’ll be needing some delicious unfussy food to balance your sojourn – enter Santiago’s Bodega Tapas Restaurant – the perfect interlude in a night of cocktail sampling. Located on Petronia Street, 3 blocks off mid-Duval in the Bahama Village neighborhood, this intimate restaurant has seating inside or outside on the porch.  Selections are imaginative, artfully executed and most importantly, yummy.  My favorite selection?  Without a doubt, the warm prosciutto wrapped dates stuffed with goat cheese – mmmmmm!

The Keys
Time for some entertainment!  The Keys on Duval Street is a fun stop for everyone who loves a piano man and can’t keep their foot from tapping out a show tune.  Reminiscent of a New York piano bar and attracting a robust range of local talent, The Keys also welcomes visiting artists to it’s nightly open microphone sessions.  I felt like we had had front row seats to a Broadway show by the time we left!

Turtle Kraals Tower Bar
While the location of the Turtle Kraal Restaurant is definitely right on the main tourist route (at the old seaport wharf) many folks pass right by and never look up. Perched atop the restaurant is a great bar with some of the best views in Key West. The bar is only open if the weather is warm and clear, but when the gate to the stairway is open…. it’s a climb that shouldn’t be missed!  This perch will give you the optimal vantage point for watching the crowds pass by, the boats move in and out of the harbor, and for watching the ebb and flow of  the Key West waterfront.  They run a great happy hour starting at 4pm, and it’s an optimal location for watching day turn to evening.

Finnegan’s Wake
Would any  bar crawl be complete without a stop at an Irish Pub? – Of course not!  You’ll find a warm Gaelic welcome on Grinnell Street, a few blocks back from the harbor at Finnegan’s Wake.  This pub has everything you need for a great time, loads of brews to select from, generous portions of good food, and live traditional Irish music performances.

These are our favorite choices for local hang outs in Key West, but we’re sure we may have overlooked one or two of your favored stops –  so we invite you to share, share, share – where have you found magic in Key West?

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Category: Featured, Florida Travel Tips