Cue the Jimmy Buffett and pour a daiquiri – we’re officially on island time! If you’re heading to the Florida Keys anytime soon (or just dreaming about it like us) this post is for you! While the LIY Team has either A.) never visited Key West or B.) hasn’t been in the last 10 years – we do happen to know a few thousand friends who have visited recently. You – our LIY Community! Today, we’re sharing all the best Key West recommendations from the Living in Yellow Community. Below you’ll find the best places to stay, best places to eat, and the best activities to plan for your next trip to Key West. Get your suitcase ready friends, you’re going to want to book a trip in 3, 2, 1 . . .
Click here to see all LIY Travel Guides!
Where to Stay
- Almond Tree Inn – Highly suggested!
- Kimpton Winslow Bungalows “2 blocks from Duval. Super convenient to everything!” -Brittaney, Florence, AL
- Kimpton Ella’s Cottages
- Simonton Court Bed and Breakfast “Walking distance to Everything, 2 blocks from Duval street, quaint and quiet and 4 mini pools!” -Grace, Granger, IN
- The Truman Annex “Great location and quiet, so close to the downtown activities and sites but quiet and relaxing for down time.”
- Key West Villas
- Southern Most Beach Resort
- The Southernmost House
- The Reach Resort
- Curio Collection by Hilton
- Hyatt Centric Key West
- Santa Maria Suites
- Casa Marina
- The Capitana
- The Perry Hotel Key West
- The Saint Hotel (Marriott)
- The Marker Key West
- Havana Cabana Key West
- Casa Marina Key West, A Waldorf Astoria Resort
- The Banyan Resort
- The Stars & Stripe House
Where to Eat
Lunch & Dinner
- Firefly Key West [Dinner + Brunch daily 10am -3pm!]
- Blue Heaven Key West [Breakfast, Lunch, & Dinner] “Great for brunch. Eat outside with live music and chickens. Lobster eggs Benedict is amazing.” -Bevin, Fort Myers
- Pepe’s Key West [Breakfast, Lunch, & Dinner] Oldest restaurant in the Keys!
- B.O.’s Fish Wagon [Lunch & Dinner] “My husbands favorite place. Funky little seafood shack. Awesome fish tacos and cracked conch. On same street as Pepe’s.” -Bevin, Fort Myers
- Conch Republic Seafood Company [Lunch & Dinner] “At the marina just minutes from Caroline Street (where Pepe’s and Bo’s are) You can feed tarpon here. Good seafood.” -Bevin, Fort Myers
- Latitudes [Breakfast, Lunch, & Dinner] “The most amazing views and upscale environment!” -LIY Follower, New Orleans
- Two Friends Patio Restaurant [Breakfast] “Great breakfast in a casual atmosphere” -LIY Follower, New Orleans
- First Flight Island Restaurant and Brewery “Dinner in the garden under the hanging lights” -Heather, Naperville
- Corner Sandwich Shop “Hidden gem that the locals love!” – Paula, Nashville, TN
- Onlywood Pizzeria Trattoria “Delicious Italian food!” -Larissa, Lawton, MI
- Sunset Pier, Ocean Key
- Santiagos Bodega
- Louie’s Backyard
- Old Town Mexican Cafe
- Hot Tin Roof, Ocean Key
- Four Marlins
- Hogfish Bar & Grill
- Boat House Bar & Grill
- Alonso’s Oyster Bar
- Square Grouper Bar & Grill
Breakfast & Brunch
Glazed Donuts // Cuban Coffee Queen
- Glazed “Best donuts!!” -LIY Follower, Easton, Ma
- Cuban Coffee Queen
- Firefly Key West [Dinner + Brunch daily 10am -3pm!]
- Moondog Cafe & Bakery
- Blue Heaven Key West [Breakfast, Lunch, & Dinner] “Great for brunch. Eat outside with live music and chickens. Lobster eggs Benedict is amazing.” -Bevin, Fort Myers
- Pepe’s Key West [Breakfast, Lunch, & Dinner] Oldest restaurant in the Keys!
- Latitudes [Breakfast, Lunch, & Dinner] “The most amazing views and upscale environment!” -LIY Follower, New Orleans
- Two Friends Patio Restaurant [Breakfast] “Great breakfast in a casual atmosphere” -LIY Follower, New Orleans
- Seaside Cafe
- Banana Cafe
- Bagatelle
- Croissants de France
Dessert
- Better Than Sex Dessert – Highly recommended!
- Kermit’s Key Lime Shoppe “Key lime pie on a stick!” -Cassie, Catonsville, Maryland
Happy Hour Spirits
Sloppy Joe’s // Flying Monkey’s Saloon
- Irish Kevin’s – Live music!
- Flying Monkey’s Saloon “Large selection of yummy adult frozen drinks” -Larissa, Lawton, MI
- The Green Parrot “Get the root beer barrel shots as night cap!”
- General Horseplay
- Dante’s Key West Pool Bar
- Sloppy Joe’s
Things to Do
Visit The Hemingway House
- Hemingway House – “If those walls could talk! Fun to visit with the many six toed cats on the property too.” -LIY Follower, New Orleans
Visit the Southernmost Point
- Visit the Southern Most Point (just to get a picture!)
Visit Fort Zachary Taylor
The Butterfly Conservatory
Go Fishing
Go fishing! Take your own catch to take to southernmost point grill.
Jeep Rentals
Sea Plane Tours
- Sea Plane “Def a spurge- but amazing and I do not even love flying 😉 ”
- Rent bikes, Scooters, or Golf Carts & Cruise the Island
- Sunset Celebration at Mallory Square – “Starts a couple hours before sunset. Street performers, stilt walkers, magicians. Best sunset views. Kind of tourist, but a must do if you have time. The kids will love it.”
- Key West Aquarium– “You can buy tickets online at a discount. Can also buy packages for multiple attractions!” -LIY Follower
- Conch Train– “Good way to see the town and learn local history. Also a good break from walking and the heat.” -LIY Follower
- The Truman House – “If you like history the Truman House is cool!” -LIY Follower
- Lazy Dog Marina “They do fantastic eco kayak tours. It’s a good day on the water and so educational as well.” -LIY Follower, New Orleans
- Dry Tortugas National Park – “Be sure and book well in advance!” -LIY Follower, New Orleans
- Visit the Key West Cemetery “Fascinating & very old gravesites & wild chickens all over” -LIY Follower
- Night Kayaking
- Smathers Beach
- Aqua Drag Show
- Rent a Catamaran
- Key West Eco Tours – Snorkel/Kayak
- Wind and Wine Sunset Sail with Danger Charters
- Trolley Tour
- Wine or Rum Tasting
- Dolphin Cruise
- Tiki Boat
- Visit a Sandbar
- Walk Duval Street
And that’s a wrap! Thank you to the entire LIY Community for all the wonderful recommendations & sharing your photos with us! Happy travels, friends!
