When you’re on vacation, it can be tough to find good food at inexpensive prices. Key West, an island in the Straits of Florida, isn’t the most budget-friendly vacation spot, but you’ll fall in love with island life. We talked to lots of locals on our recent trip to the Keys and discovered many great places to try, all at lower price points. We also learned that happy hours are a fantastic way to get a great bang for your buck.
Thanks to some of these restaurants for hosting me. All opinions are my own.
Kaya Island Eats
Kaya Island Eats was a stop on our fantastic Southernmost Food Tasting and Cultural Walking Tour and won raves from everyone in attendance. Chef Taylor and crew serve up island-fusion eats in a casual, come-as-you-are atmosphere. Don’t let the small door front fool you; part of the charm of Kaya is all the nooks and crannies out back in the courtyard. Go in and explore the bars, have a cocktail, listen to music, and enjoy all the fresh creations on the menu. Kaya has a daily happy hour from 4-6 PM. Try their famous tuna poke nachos.
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Half Shell Raw Bar
This gem on the waterfront has been in town since the early 1970s and was packed the Tuesday night we were there. We came just after happy hour, so we didn’t get in on those specials, but our meal was one of the best we had during our stay.
Oysters are the signature dish at Half Shell Raw Bar, so we asked our waitress to bring us oysters. If you like oysters, Half Shell is the place to be. That goes for any raw seafood, since their raw bar is known far and wide as one of the best.
According to the locals we talked to, their happy hour is one of the best, too, and features all the raw bar goodness including half-priced oysters on the half-shell, peel-and-eat shrimp, steamed clams, and conch fritters, among other selections. Next time, I’ll grab a few more friends and try the SS Minnow Boat. This mega-meal serves 4-6 and includes oysters, clams, shrimp, and chilled lobster tail.
For dinner, I tried shrimp, scallops, and mahi skewers with grilled vegetables. Served with new potatoes, I loved the flavor and lightness of the meal. We grabbed the coconut shrimp appetizer to start things off, and that may have been my favorite appetizer of the trip. Those crunchy, deep-fried shrimp dipped in sweet and sour sauce hit the spot.
We made the super smart decision to finish things off with the bread pudding dessert. I know a good bread pudding when I taste one, having taste-tested my way through New Orleans’ bread pudding a few years ago. Half Shell Raw Bar’s warm bourbon sauce, ladled on top and dripping down the sides, makes theirs completely over-the-top delicious.
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We’d heard from so many folks about Kermit’s famous key lime pie on a stick that we had to get down there and try it for ourselves. But first, we had lunch. Kermit’s Cafe is a casual spot where you order at the counter and grab a table out front. We chose to sit right up against the street to get in on all the good people watching. The streets of Key West are never dull, and we found plenty to keep us entertained as we sipped our homemade Bloody Marys.
We chatted with Diane, the lovely manager who’s one of the few people we met actually from Key West, and she recommended a few things from the menu. She brought me a steaming bowl of the Damn Good Chili, which was darn good. The homemade poppy dressing on the bean salad was also really tasty. All the sauces and dressings are made in-house. If you go, you must get the key lime pie; it has been voted best on the island (by locals) since 2018. The grand finale for me, was in fact, that key lime pie. It lives up to all the hype, served on a stick and dipped in chocolate.
Make sure you stop into Kermit’s Key Lime Shop shop attached to the cafe. You’ll find all sorts of sweet and savory goodies to try. We loved the mini cookies, and yes, they do have the mini key lime pies on a stick. They will even ship everything straight to your home.
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Conch Republic Seafood Company
We had just been told that our sunset cruise was rained out. So what to do? Head over to the local watering hole and watch it rain. That’s exactly how we ended up at the Conch Republic for happy hour.
We had a great time watching the boats bob up and down in the harbor as the skies opened up. Rain isn’t so bad when you’re not stuck in it, and it’s even better when you’re nursing a cocktail, munching on fresh salmon patties and meeting new friends. Conch Republic allowed us to do all three. It’s a fun place to hang out, even in good weather, and their happy hour is legendary.
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We walked around Key West a lot, and somehow we ended up in front of Ram’s Head more than once. We took this as a sign that we were meant to be there. The music was blasting, and it looked like everyone was having a good time, so we ventured in and had a blast. The Bloody Mary bar gets rave reviews, and the happy hour, with loads of half-priced appetizers, got rave reviews from everyone we talked to.
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If a restaurant has been around for over 100 years, it must be doing something right. Serving breakfast, lunch, and dinner seven days a week, Pepe’s draws a crowd for their homemade food any time of day. The oldest restaurant in Key West is worth a stop just to see the cool history of the place. Check out their happy hour from 4-6 PM.
Key West has plenty of inexpensive places to grab a great meal. To find the best places, be flexible with your plans, be prepared to wait a little while for a table, and avoid prime time if you can. Above all, enjoy yourself and have a great time.
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