Who doesn’t love happy hour? It’s the perfect way to enjoy a few beverages and sample some of the cuisine from a restaurant without committing to an entire meal. When I first moved to Key West, I searched diligently for an all inclusive list with no success. Here you will find an extensive list of happy hours, categorized by location so you can maximize your happiest time. (updated 7/2021)
Lower Duval (Caroline Street to Mallory Square)
By far my favorite happy hour in this category is Bagatelle. In fact, Bagatelle is one of my favorite restaurants on the island. Another fun happy hour in this part of town is General Horseplay: roll the dice for the price of your drink in a Bill Murray themed bar.
Mid Duval (Caroline Street to Catherine Street)
This category is tough as there are so many happy hours on mid Duval Street. Manic Monday at 22&Co is ridiculous not to mention my favorite bar in Key West. Make sure you get one of their signature Martinis and all the drinks come with free glitter. Lost and Found has a broad selection of happy hour menu items to please every palate. If upscale is your thing visit Thirsty Mermaid ($5 Mermaid Lager and mussels) or Santiagos Bodega which are two of my favorites in this category.
Upper Duval (Catherine Street to the Southernmost Point)
Martin’s is the top contender in this category for happy hour as their tapas menu is equivalent to a fine dining experience with choices from lobster bisque to lamb chops all 1/2 off.
Another tough category as the vibe changes when you wander from Duval to the more local side of town. Marilyn’s is my neighborhood go to happy hour and they offer a local discount. Dante’s shares a kitchen with Prime, our upscale steak house, so the food is spectacular and is a great people watching location with a public pool as part of the bar. Half shell has great seafood for happy hour and Onlywood 1/2 off wine with brick oven fired personal pizza for $9
Stock Island and beyond……
Roostica is a must visit for Stock Island. Brick oven fired pizza and an expansive wine list, not to mention I love their catch phrase “Make Marinara Legal”.