Key West, Florida
When you need to escape the cold winter in Cleveland, Key West is the perfect long weekend or week-long getaway! We’ve detailed some of our favorite spots for you to enjoy when you visit below.
This blog contains affiliate links, meaning: at no additional cost to you, we earn a small commission if you click-through and make a purchase. We appreciate you using our links to explore and book travel!
First off, you’re going to need a place to stay. We recommend:
Santa Maria Suites Resort - this is where we most recently stayed. It offers rooms with two separate bedrooms with on-suite bathrooms, plus a spacious downstairs with a pullout sofa and a kitchen. We loved having all of the space to share with another couple. Its located on the opposite end of Duvall from Mallory Square, which was a quiet location we really enjoyed.
Fairfield Inn & Suites by Marriott Key West - this one is a bit farther from the heart of town, but is a great group travel option… note there are two Fairfield’s on this Island and this is the one we prefer.
There are plenty of amazing hotels in Key West, if you are ready to pay a premium - we’ve had good experiences with Key West Marriott Beachside Hotel, Kimpton Key West, Ocean Key Resort & Spa, or Margaritaville Beach House Key West.
You can always try Airbnb in Key West as well - just read the reviews! Pro-tip, always check to see if you can connect with the hotel/inn/location directly and you may be able to skip some fees.
You’ll be able to get around Key West via walking, biking, and rideshare so a car is not necessary. Plus you can even rent a golf cart or a scooter for the weekend!
Arrive in Key West Friday:
Get situated at your hotel and bask in the sunshine at your pool, or take a stroll down Duval to see what you need to explore that evening!
What are you feeling for dinner? As of February 2022, we recommend booking reservations for dinner on the island when you are able.
Upscale dining: Milagro Restaurant and Bar or Bagatelle
For the Views: Louie's Backyard, Hot Tin Roof Restaurant, or Sunset Pier
Seafood: Alonzo's Oyster Bar, Half Shell Raw Bar, or The Stoned Crab
American: Fogarty's or First Flight Island Restaurant & Brewery
Enjoy dessert at Better Than Sex - A Dessert Restaurant, make sure to make a reservation about a week - two weeks in advance!
Drinks: Your visit to Key West is not complete without trying a frozen cocktail. Our favorites are at Flying Monkeys and Fat Tuesdays.
Saturday:
Wake up and grab a donut at Glazed Donuts
Breakfast: Banana Cafe, Sarabeth's Key West, or Cuban Coffee Queen Downtown
Or Brunch: Ocean Grill & Bar (Bottomless Mimosa's & Bloody Mary's @ Brunch 10am-3pm - $7.95), or Rams Head Southernmost (Bloody Mary bar)
Your afternoon:
Explore: The Ernest Hemingway Home and Museum, or Key West Butterfly and Nature Conservatory, take a photo at Southernmost Point (get there early to avoid a wait), hang out at one of the beaches, see more ideas here.
Lunch:
Your Evening:
Catch the sunset at the famous Mallory Square, grab dinner, and then hit up the nightlife on Duval + beyond
Dinner Suggestions:
Our favorite bars include:
Sunday:
If you can wake up early, head to Blue Heaven and get in line for the best food you’ll enjoy all weekend. If you don’t get there early, be prepared to wait!
Head back to the airport and rave on social media about your visit. We’d love it if you’d tag us in your photos!
Additional Ideas:
If you have a full day - take a trip to Dry Tortugas National Park.
Book a sunset cruise (we preferred Sunset Cruises’ live music option, but there are plenty of other options as well with other vendors).
Book an excursion, like jet-skiing around the island, snorkeling, parasailing, dolphin watch, glass-bottom boat tours + more!
