Best Places to Eat in Key West

Open air seating at First Flight Brewery restaurant.

Key West is touted for having “the southernmost” everything! That’s why as soon as December hits, people flock to Florida. The island feels exotic and tropical without the need for a passport! Because it’s basically paradise, it’s also prone to overcrowding and expensive price tags. Spending a fair amount of time on the island, I have compiled some of my favorite places to eat (and drink.) Vetted mostly by trial and error, here are the best places to go while in town so you can get right to the good stuff!

Eggs benedict and Bloody Mary at Blue Heaven
Eggs Benedict (try the “BLT” with Florida Lobster) for a delicious breakfast with chickens at Blue Heaven, Photo Credit Wayfaring Mandy

Blue Heaven

This is my hands-down favorite spot for the best spot for breakfast in Key West. If you’re looking for the best things to do while in Key West, make sure you treat yourself to an incredible breakfast at least a few times! The portions are gargantuan. My favorite is the “BLT” Benedict. Blue Heaven offers ample shade and if dining with fowl is your jam, they’ve got you covered. Resident chickens and roosters are happily scuttling around the open air restaurant. Blue Heaven also has a gift shop and sells their baked goods there (including the Banana Bread you can opt-in on as your side carb!) I bought a loaf before departing the island.

Rooster strutting along the ground at Blue Heaven restaurant.
Rooster strutting along the ground at Blue Heaven restaurant in Key West, Photo Credit: WayfaringMandy

Little Pearl

A Chef’s Tasting menu of delightful seafood prepared in ways that make flavors pop, you’ll want to snag a reservation (and set aside about two hours) for this evening feast. If you don’t care about the sunset one evening, getting a reservation might be easier at the earlier seating. This is a very cozy spot so there are limited tables at each seating time. This is perfect for a celebration but is perfectly casual, so no need to stress over formal attire. Parking is a bit of a bugger, so plan ahead; Little Pearl Key West is a spot which should make your itinerary without a doubt.

Beer selections and drink coaster.
First flight selections at First Flight Brewery, Photo Credit: WayfaringMandy

First Flight Brewery

Most come for the beer, but the menu has really lovely variety. Pretzel bites from the Happy Hour menu and fish tacos (a no brainer from the dinner menu) delighted my taste buds and my stomach. So many tasty sounding options! A flight with a mix of regular brewery offerings and some seasonal varieties was a fun way to drink through their beer menu. There are other domestics and drinks available as well. The history of First Flight Brewery, being the birthplace of Pan-American World Airways is what drew me to want to visit but the food will be what brings me back! The seating is open air and again welcomes many chickens and roosters, as well as live music from the bar across the street.

If I’m Being Honest…

While you should always make decisions for yourself when it comes to travel planning, after careful research and consideration, I feel it’s only fair to share those places (if I’m being honest) I might not waste my time, if I had it to do again.

Oysters Rockerfeller at the Stoned Crab
Oysters at the Stoned Crab, Photo Credit WayfaringMandy.

Pepe’s was a restaurant I heard great things about and being a bit of a history buff, I liked that it was the second oldest restaurant in Florida, after the Columbia in Tampa/Ybor City. It wasn’t bad and it had character, but nothing about the food blew me away. Pepe’s was just average with an interesting history. It was busy though, so maybe I’m the outsider on this one!

The Stoned Crab might have been the seafood spot to make sure to visit before you leave Key West ten years ago, but changes in ownership and steep prices, along with subpar service experiences have put this former favorite to the bottom of the list for me now. Nothing about our most recent experience made it stand out much more than a Red Lobster.