Family Getaway to Key West – 5 Days of Sunshine to Escape the Chicago Winter. February 2020
In February 2020, we decided to treat ourselves to a winter break and fly to a sunny destination: Key West, Florida. Our stay was a wonderful family getaway, with a perfect mix of cultural discoveries, relaxation, and fun activities, all in a tropical atmosphere. Here's a glimpse of our enjoyable escape to the Keys.
Day 1: Arrival in Key West and First Sightseeing
We took a direct flight to Key West and landed in this little slice of paradise bathed in sunshine. Upon arrival, we were greeted by a pleasant sea breeze and palm trees swaying gently under the blue sky. After picking up our rental car, we drove to our accommodation. We had chosen a charming hotel, the Ocean Edge Resort, on the marina near the town center, so we could easily explore the island on foot.
In the late afternoon, we strolled along Duval Street, the main street, soaking up the local atmosphere. This street is full of colorful shops, bars, and restaurants where you can enjoy local cuisine with Caribbean influences. We ended our day with a delicious dinner of fresh seafood, where everyone could enjoy naturally gluten-free dishes, such as grilled prawns and conch salad.
Day 2: Discovering the History and Beaches of Key West
The next day, we started with a visit to Ernest Hemingway's house. This iconic place allowed us to learn more about the writer's life and to discover his famous six-toed cats who still roam the grounds. The children especially enjoyed listening to anecdotes about the author's eventful life and exploring the house's lush gardens.
In the afternoon, we headed to Fort Zachary Taylor State Park, one of Key West's most beautiful beaches and a fort steeped in history. The crystal-clear waters and magnificent scenery provided us with an ideal moment of relaxation as a family. This fort, built in 1840, played a key role during the Civil War and then the Spanish-American War. Today, it is a designated historic landmark.
At the end of the day, we went to Mallory Square for the famous sunset. The street performers, the music, and the lively atmosphere added a touch of magic to the moment.
Day 3: Kayaking Excursion and Bike Ride
On the third day, we took a short kayak trip which allowed us to observe the pelicans.
In the afternoon, we rented bikes to explore the island at our own pace. Since Key West is a relatively small island, it's the ideal way to discover the quaint little streets, the colorful houses, and even take a ride to the Southernmost Point Buoy , the southernmost point of the continental United States.
Days 4 and 5: Boat Trip and Unforgettable Sunset
To end our stay, we opted for a catamaran excursion. We wanted to explore the turquoise waters of the Keys and snorkel around the coral reefs. The children were thrilled to see the colorful fish and to sleep aboard this magnificent catamaran. The sunset was simply magical.
Day 5: Shopping and Returning Home
For our last day in Key West, we decided to do some souvenir shopping. We explored the island's many artisan shops, where we found local products such as shell crafts and sea-inspired items. We also took the time to enjoy one last Key Lime Pie , a local specialty that's fairly easy to find gluten-free (check the recipes!), made with lime, which we loved.
Why Choose Key West for a Family Trip?
In conclusion, our family trip to Key West was a lovely getaway, filled with moments of togetherness, discoveries, and relaxation under the Florida sun. Between its beaches, museums, water sports, and welcoming atmosphere, this small island in the Florida Keys has everything to please.

