At least one night in Key West you should treat yourself to the phenomenal food at Little Pearl. Enjoy the Japanese inspired tasting menu, based heavily in seafood. You’ll get to make a selection in each section – don’t miss the BBQ eel if the option presents itself. It also prides itself on its wine […]
Itineraries
Eat & Drink
Little Pearl
Afterdeck Bar at Louie’s
Louie’s Backyard is comprised of both a house and a porch with incredible views over the water. The food is fresh and contemporary. It’s a particularly excellent spot for brunch or lunch. Here you’ll see more locals than tourists. The Afterdeck Bar is right on the Atlantic and serves up delicious cocktails. Stop at Dog […]
Little Room Jazz Club
Walk up a blue lit staircase and enter this intimate and candlelit music venue. You can check the lineup online before to see who’s playing (and this place does get artists from all over the world), but regardless of the artist, it’s a perfect after-dinner venue to finish your evening. Two good drinks include the […]
Moondog Cafe
This spot is quite close by to the Ernest Hemingway Home and Museum. It’s a great place for vegetarian and vegan fare, brunch, and fish tacos. Don’t miss their homemade pastry case – we recommend perusing before ordering dessert. It offers both indoor and outdoor dining.
Salute! On The Beach
Want to dine on the beach? This is your place. Set on Higgs Beach, you can’t get closer to ocean-front dining. Enjoy especially the fresh fish or pasta. Check ahead to see if there will be live music while you dine.
Blue Heaven
This is on all the best of Key West lists and for good reason. Set in a beautiful backyard with a tall banyan tree towering above, this relaxed restaurant serves food heavily spiced with Caribbean and Creole influences. More often than not there’s live music. Hopefully you don’t mind a few chickens strutting around while […]
More
Eaton Street Seafood Market & Restaurant
This is both a seafood market and restaurant serving up excellent and casual seafood. Here you’ll find more residents than tourists, and the best lobster rolls and fish dip in Key West. The fresh catch of the day is a can’t-miss as well. The only seating is outside, but shady. Stroll up to the counter […]
Date & Thyme Organic Cafe and Market
This excellent health store and cafe serves up tasty coffee, matchas, smoothies, and sandwiches (including vegetarian and vegan options). While you can take it to go, they also have a nice seating area right out front.
Cuban Coffee Queen Roasters
Probably the most famous coffee in Key West, you should try Cuban Coffee Queen. Here you can grab an extra strong cafe con leche or a Cuban sandwich. While this not necessarily our favorite coffee in Key West, it’s a solid option and, as we said, this is an institution and you’ll see it top […]
Sandy’s Café
Part laundromat, part cafe, this is the place to go for a Cuban sandwich. You’ll order from the sidewalk through a takeout window. Also try their excellent Cuban Coffee.
Papa’s Pilar Rum Distillery, Hemingway Rum Company
This Rum Distillery offers both tours and an excellent bar with craft cocktails, and, more often than not, live music. Named after Ernest Hemingway “Papa” and his ship “Pilar” they embrace his spirit – you can even sidel up to the bar and take a selfie with the life sized statue of him. The cocktails […]
Seaside Cafe at the Mansion
An outdoor cafe abutting the southernmost house, a historical hotel from 1897, grab a seat and enjoy famous mojitos, margaritas, or a mango daiquiri. Their pizza is also excellent. This makes a nice place to enjoy sunset.
Green Parrot Bar
Built in 1890 as a grocery store, this is now fondly known as the oldest bar in Key West. This saloon can have locals outnumbering tourists on any given night. This is an excellent place to enjoy a dive bar while listening to great music.
See
Dry Tortugas National Park
This is one of the hardest national parks to get to in the country, but it’s well-worth it for its beautiful waters, fantastic sea life, and history. The archipelago is about 70 miles off the coast of the Keys. This was the site of the wreckers during Key West’s heyday. These wreckers made a living […]
The Key West Butterfly and Nature Conservatory
There are more than 50 species of butterfly and 20 species of exotic birds from around the world in this glass conservatory. Here, you can learn everything you could ever want about butterflies, however the best part is simply wandering the conservatory itself with hundreds of butterflies everywhere you look. It’s magical. This is also […]
Truman Little White House
The Harry S. Truman Little White House is where President Truman spent 175 days of his presidency. Before that the same building served as a naval station’s command headquarters during the Spanish-American War. You’ll visit the house as it was in 1949 and see the rooms where the Trumans lived and worked during their time […]
Do
Fort Zachary Taylor Historic State Park and Beach
Fort Taylor was built for defense during the American Civil War and the national historic monument remains, but so does the lovely beach it is set upon. If you love history, start by visiting the monument which houses the largest collection of Civil War military equipment in the world and learn about the fort’s role […]
Smathers Beach
This is Key West’s prettiest and largest beach which runs along the southern shore of Key West for nearly 2 miles. The sand is brought in from the Bahamas, making it soft and fine. The water is calm and perfect for a swim or dip. The beach is clean, peaceful, and relaxing, and you can […]