When you are in Key West, you drink. You have a cocktail at brunch. You explore the town with a beer in your hand. And you enjoy the bargain that is happy hour. It’s not only an excuse to drink; it also provides you with an affordable way to eat more seafood.
Best Happy Hour: Solo American Bistro
610 Greene Street
Happy Hour: 4 – 7, 1/2 off drinks & select menu items
Most places offer beer, house wine and well drinks at half price, but Solo American Bistro also extends their entire cocktail menu. Try the ginger margarita with graham cracker on the rim or their ridiculously refreshing cucumber cocktail, organic vodka with muddled cucumber, sugar, basil, lemon and a splash of soda. They also have a great selection of wines and beer.
I highly suggest taking advantage of the discounted food as well. We enjoyed the yellowfin tuna tartare, with arugula, seaweed salad, tobiko caviar, avocado wasabi aioli and shrimp chips. I also suggest one of the flatbreads. We went for the four cheese, with Gruyere, gouda, shaved parmesan, gorgonzola, roasted onion and garlic on a thin, crust with just the right amount of chew. We also enjoyed the conch and shrimp fritters, served with chipotle cilantro honey mustard and lobster mayo dipping sauce.
The restaurant’s interior is exquisite, with comfortable leather booths lining the exposed brick. The covered patio looks out onto the street. The vibe is groovy whether you’re in or out.
806 Caroline Street
Happy Hour: 4 – 6:30 PM, discounted drinks and oysters
Established in 1909, this Old Town cafe claims to be the oldest eatery on the island. They served my very first oysters of the trip, so I’ve got a sweet spot in my heart for them. It’s a very friendly place serving traditional diner faire, like a pork chop-smothered steak, which I never tried but would like to mention.The margaritas are on the sweeter side but are pretty good.
231 Margaret Street
Happy Hour: 4:30 – 6:30 PM, deals on food and drinks
If you want fresh fish at a steal, this is your place. This waterfront restaurant gathers seafood fresh from their fish market next door and serves up appetizers for about $5 each. We enjoyed a dozen monstrous oysters for $6 and fried calamari for $5, in addition to half priced beers. Though they share the same owners, our happy hour oysters weren’t quite as tasty next door at Turtle Kraals. The happy hour specials are the same, so I recommend enjoying the better drink selection at Half Shell. Try to grab a seat by the water and watch the parrot fish.