Top 5 places for an afternoon libation in Key West

There is nothing that says, “I’m on vacation” quite like the decadence of settling in for relaxing mid-day cocktails.   These lovely spots are my favorites for whiling away a long afternoon in Key West…

#5… The After Deck at Louie’s Backyard

You’d be hard pressed to find a more “waterfront” spot than this.  The After Deck at Louie’s Backyard is not only a great place for an after dinner cocktail, but is a great place to hang out after a delicious lunch.   Off the Old Town beaten path, it feels as if you’ve stumbled upon a little secret.  Great views, great bar, great food.

Photos of Louie's Backyard, Key West










Photo Courtesy of TripAdvisor

#4… Hog’s Breath Bar

Although I typically avoid the Duval Street scene, and although the place isn’t even on the water, there is just something magical about a mid-day Corona at the Hog’s Breath Bar.  Maybe it is the constant live music, maybe it’s the “tucked away” feeling (from Duval Street), or perhaps it is the fact that when I’m back in real life, I can log in and see “my seat” from the Hog’s Breath Cam.  Regardless, when we find ourselves there, we feel like we are on vacation.  Most times we’ve landed there, it hasn’t been at all crowded.  But the spell seems to break once 4:00 rolls around and it starts to feel more like a tourist spot.

#3… Blue Heaven

Since you will likely wait quite awhile for a table at this uber-popular Key West staple, don’t be in a hurry.  Just make plans to sit back, relax, and enjoy the best restaurant wait on the face of the earth.  I fondly recall a Bellini (or two?) one lovely Sunday afternoon.  Stretch your toes in the sand, listen to some live music, and enjoy the quintessential Key West of Blue Heaven, chickens, cats, and all.

Important Brunch Tips:  Although you are in Key West, you are still in the South where no one is allowed to drink before noon on a Sunday.  Avoid disappointment and plan accordingly.  Order some banana bread to tide you over, get the lobster benedict if you are at all inclined and stay as long as possible.

#2… Sun-Sun Bar at the Casa Marina.

One of the simple pleasures of Key West is simply walking around the residential neighborhoods, particularly the Casa Marina district.  After all that walking, you’ll need a Corona Break, no doubt.  Take a load off at the Sun Sun Bar at the Casa Marina Resort (and don’t miss touring this historic property itself) located right between the two beautiful twin pools and the Casa’s beach.  If you are staying at the resort (which we usually do whenever we are in town), you absolutley must take advantage of a long day by the pool, complete with cocktail delivery direct to your chair and even complimentary afternoon popsicles.

#1…  Latitudes on Sunset Key

Make a reservation for lunch, catch Sunset Key’s shuttle boat at the Marina and set sail for a lovely afternoon on Sunset Key, an island just off of Key West, home of the Sunset Key Guest Cottages Resort by Westin.  Another toes in the sand restaurant, this is a can’t miss Key West spot, although it takes a little pre-planning.  The boat ride is a blast, the food delicious, and the view and setting is hard to beat.  Again, order a long lunch, several margaritas and hang out for as long as possible before taking the oh-so-pleasant journey back to the main island.

Enjoying my favorite refreshment at Latitudes on Sunset Key



  1. […] that to concentrate on the delicious food and tropical breezes.  The afterdeck bar is one of the best places for a drink in Key West, so plan to hang out there before heading back for an evening beach stroll or swim at […]

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