KEY WEST TRAVEL GUIDE
Florida’s Conch Republic is known for its tropical pastels and picturesque sunsets. Closer to Havana, then Miami, the island is the furthest city south in the continental United States. Key West has a great blend of Architectural styles that can not go unnoticed. Caribbean accents layer onto traditional “cigar- maker’s cottages” and decorative Victorian-era elegance. Sunshine, vibrant greenery, laid back locals, and salty characters give Key West an authentic appeal to any visitor.
WHERE TO STAY
KIMPTON WINSLOW’S BUNGALOWS
This hotel is a charming destination in Key West’s historic old town. Just two blocks from Duval Street, the hotel sits tucked away within a tropical lush landscape.
At each bend along the meandering brick pathways, you can find hammocks swinging and hotel guests sipping cocktails. The independent bungalows make for a unique hotel experience paired with all the luxury IHG amenities you would expect.
HOW TO GET AROUND
BIKE
Take a bike ride around the island. I would say most would feel comfortable cycling. It’s a fun & easy way to get around. Some hotels offer complimentary bikes.
We rented from Eaton Bikes. We wanted to cruise together on a tandem bicycle during our trip! We called to make the reservation, and they dropped off the bike at our hotel & picked it up the next morning.
WALK
Key West is very walkable and pedestrian friendly. However, depending on the time of year you plan to visit, Key West can be extremely hot and humid. If you decide to walk, remember to stay hydrated and have a good comfortable set of walking shoes.
RIDE SHARE
If you are flying into the airport, a quick ride share will get you into the city center/old town within 10 minutes.
FLY
This might be a great option to help save time and might be the easiest way to get to Key West, unless you would like to take a Road Trip! Many commercial carriers have connections and you can easily pick up a rental car, ride share or taxi to take you to your accommodations.
TOURS
Take the opportunity to get know the island by a guided tour. See the major points of interest while relaxing! Key West has a few notable options:
Conch Tour Train
Old Town Trolley Tours (Guided Hop on-Hop Off)
PRO TIP: We saw a lot of people renting scooter’s and golf carts. While they seem like a good option, I only recommend if you are comfortable driving.
EAT
El Meson De Pepe
Superb Cuban food with a lively atmosphere right off of Mallory Square.
MoonDog Café and Bakery
A small charming cottage across the street from the Earnest Hemingway House. It serves as a casual dining spot off Duval street with outdoor patios.
Amigos Tortilla Bar
Sit along the bar facing the street and soak in Key West culture while sipping a margarita. This is another casual eatery with great tacos.
Bagatelle
The perfect brunch spot right on Duval street, near Mallory Square. The historic home was built in the 1800s, and was only converted to a restaurant in 1979. The balcony sets the stage for all the flavors of the Florida Keys.
Eaton Street Seafood Market & Restaurant
Fresh, Local and highly recommend the Lobster Roll! (Picture below is worth a thousand words.)
Cuban Coffee Queen
Grab a morning café con leche and enjoy the imposing roosters and hens hovering over your Cuban breakfast sandwich- the experience is worth the visit! Grab a fresh bag of coffee next door as a souvenir.
DRINK
The Green Parrot Bar, 601 Whitehead St, Key West, FL 33040
Sloppy Joe’s Bar, 201 Duval St, Key West, FL 33040
Captain Tony’s Saloon, 428 Greene St, Key West, FL 33040
The Littlest Bar in Key West, 124 Duval St, Key West, FL 33040
Key West First Legal Rum Distillery, 105 Simonton St, Key West, FL 33040
TO DO
THE EARNEST HEMINGWAY HOME & MUSEUM
Take a guided tour of the Spanish colonial mansion. Its iconic Pantone 618 C green shutters match the lush landscape and shade the multiple lounging six-toed cats! Learn more about the American writer and his passion for traveling and adventure through the collected antiques and architectural details of the house.
KEY WEST LIGHTHOUSE AND KEEPER’S QUARTERS MUSEUM
Check out the historic lighthouse (built 1848) and now operated by the Key West Art & Historical Society. On a clear day climb the 88 steps to see the entire island!
SOUTHERNMOST POINT (Buoy)
Obligatory photo stop. The southernmost point of the continental United States is a Key West iconic landmark (built 1983) and marks “90 miles to Cuba”!
DUVAL STREET
This popular street is the center of all the action in Key West. Shop for anything from original artwork at artisan galleries to famous saloons, classic T-shirt shops and cafes, there’s plenty for everyone. “Duval has it all.”
KEY WEST MUSEUM of ART & HISTORY at The Custom House
A perfect example of Richardsonian Romanesque architecture and a great stop to discover more of the history of the city.
TENNESSEE WILLIAMS EXHIBIT
One of America's foremost playwrights called Key West home for thirty four years. Take a self guided “tour” looking at artifacts and photographs of one of America's greatest literary figures.
MALLORY SQUARE
The stage for the most spectacular sunsets in the city. A waterfront tourist plaza with a nightly celebration including musicians, performers, and food carts rounded out by a perimeter of bars and restaurants including Margaritaville.
KEY WEST BUTTERFLY AND NATURE CONSERVATORY
The magical glass-domed conservatory houses over 50 species of butterflies and multiple exotic birds including two flamingos! Walk slow and stop often. Butterflies will flutter past you and some may even land on you!
Pro Tip: The conservatory is small, do not rush, and take your time and enjoy the serene experience. Take your camera and be patient, but then I also encourage you to put the phones/cameras away and soak in the beauty of the space! It was one of my favorite stops in Key West!
