🍹 Cocktails and More in the Conch Republic 🍹

 

Key West, Florida is a popular destination, especially in the winter months when people are trying to escape to warmer weather, but not infernally hot weather like July and August.

First, we’ll set the scene by saying there is a party atmosphere in Key West all year long. And they sure love any excuse to have a parade! It’s no wonder folks like Ernest Hemingway and President Harry Truman felt drawn to this place. It’s easy to find a list of the “must do” bars for tourists in town, which includes Sloppy Joe’s, Captain Tony’s and the original Margaritaville location. And while tropical drinks are everywhere, there are also some places to get great craft beer and cocktails in the Conch Republic!

Tropical climates are great for sipping dark rum, especially if it’s locally made!  Key West has two main rum distilleries. Both are open for tours and tastings. Our favorite for both is Hemingway Rum Company, home of the Papa’s Pilar line (named for the author’s favorite boat, which was named for one of his favorite ex-wives). There is a small charge for a tour, well worth it for the experience and tasting at the end. They also offer cocktail classes separately for a small fee.

Key West First Legal Distillery is the other option in town. Yes, the name means they were the first to open once distilling became legal. They’ve been operating since 2013. They offer free tours and tastings and it’s definitely worth checking out!  They also have a bar onsite that makes tasty rum drinks like Mojitos that you can even take with you.

If you want to try lots of rum from different parts of the world, including the local brands, then the Rum Bar at the Speakeasy Inn is your place to go! They make just about every rum drink you can imagine, and you can do flights of rum and other spirits. It’s a great way to get a taste of the islands (along with wine, beer and a full bar, of course). Their front patio is a cool place to people watch on Duval Street.

And if you’re wandering up Duval Street, don’t blink or you might miss the Smallest Bar in Key West. That’s literally the name of this tiny watering hole that describes itself as “about the size of a jail cell.” But if you miss it, you’ll be missing a fun little spot for some good cocktails and lively conversation. 

As we mentioned, there are also places to get great bourbon, beer and wine in Key West.  Our “go to” spot has been The Roost. The bartenders make fantastic classic cocktails like Old Fashioneds and Manhattans but they also have a great wine selection. This is the one place we would suggest checking out for a great cocktail experience (once you’ve done the necessary stops we mentioned earlier). It’s a bit #offthetipsypath but definitely a #tipsypick!

Another excellent cocktail bar is Berlin’s. The atmosphere is about as far away from Duval Street as you can get, with lots of leather seating and jazz playing over the speakers. They have an excellent cocktail and wine selection. But in case you need reminders that you are in Key West, the bar overlooks the harbor and has a fantastic view at night.

If you prefer wine, there are several wine bars that fit the bill. Vinos on Duval Street is where we usually visit. The staff is friendly and knowledgeable. They also have charcuterie boards and other nibbles for a reasonable price. Grand Vin Wine Bar is a combination bar and wine store with a wide selection. There’s even a winery – Key West Winery. We’ll check that one out on our next visit.

And not to be left out, there are a number of craft breweries on the island (and a few others if you want to make the drive up or down Highway 1). Since we like history, First Flight Island Restaurant and Brewery is our go to stop for a “flight” of craft beers. It’s located in the old Pan-Am airways office just a few blocks from both the Hemingway House and the Little Truman White House. They have an extensive food menu as well as a full bar. That pretty much covers everything for us! Waterfront Brewery is probably the largest brewery in the Florida Keys, with an expansive space near the harbor in Key West. Their beer menu is also extensive along with their food and other beverages. It’s hard to go wrong with either of these #tipsypicks!

Speaking of food (and the island’s largest Bloody Mary bar), we recommend Ram’s Head Southernmost for brunch or great food and a patio any time of the day – not to mention drinks in buckets for sharing. They also carry a full lineup of beers from Delaware-based Fordham & Dominion brewery.

And finally, if you just want to let someone else give you the grand tour so you don’t have to decide where to start and finish, there are some great pub crawls and food tours to choose from! You can even make your own by starting around Mallory Square and seeing how far down Duval you can get before your liver gives out (with a short detour to The Roost, for sure!)

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