Travel: A Family Day in Key West

Key West has long been known as a countercultural, against the grain kind of spot in the United States, where people who want to march to the beat of a different drummer could thrive. Key West is also known as the Conch Republic, a micronation separate from the United States.

One of my favorite high school teachers who nicknamed me “Hippie” always used to tell me, “You need to go to Key West. That’s where all the old hippies go.” His advice stuck in my mind and it became a place on my to-visit list. And this December, we finally went.

Now an educator myself with family in tow, we made the long drive over  the series of bridges and islands you must traverse to reach Key West. Evidence of the hurricane lie heaped on either side of the road, bearing testament to the fact that we are all at the mercy of nature and we best treat our planet with care.

The Southernmost Point Monument

The Southernmost Point monument marks the farthest south you can go in the continental United States. At this point, you are just 90 miles from Cuba. Lines form early for this popular photo spot in a neighborhood full of sprawling Victorian homes and wandering chickens. How popular? It’s one of the most photographed sites in the U.S. so get there early if you want to avoid a long wait.

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Family photo op at Key West’s Southernmost Point monument.

Conch Train Tours

Conch Train Tours offer an easy way to traverse the Old Town area while hearing more about its history and culture. Key West is a walkable town but this tour company’s small vehicle can wind down the island’s smallest streets.

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Hop on and off where you like on Key West’s  Conch Train. (Image: Best on Key West)

El Maison de Pepe

Visit El Maison de Pepe to enjoy Cuban food right by Mallory Square and the Key West Memorial Sculpture Garden. Sit inside to enjoy the air conditioning and whimsical art; sit outside to enjoy people and chicken-watching.

El Maison de Pepe has been serving Key West tasty Cuban food for over 30 years.

Key West Lighthouse

The Key West lighthouse is right across the street from Hemingway’s house. Climb the 88 winding stairs for the best view of the island.

The Key West lighthouse has stood watch over the island since 1848.
The views and breezes at the top of the Key West lighthouse are a delight.

Hemingway’s House

The Ernest Hemingway Home and Museum  is a beautiful 1851 house and its lush grounds. The house is decorated with many items from Hemingway’s travels around the globe. Whether you are a fan of his writing or not, visit for a glimpse of old Key West and to pet those polydactyl (6 toed) cats.

Hemingway House dining room
Cats rule at the Hemingway House. Two take a nap on his bed with a headboard that used to be part of an old temple gate.
Resting a minute on the Hemingway House porch to enjoy the fresh air and Key West vibe.

Mallory Square & Around Town

Mallory Square is home to Key West’s internationally famous daily sunset celebration. Two hours before the sun sets, the square is filled with street performers of all kinds: musicians, jugglers, acrobats, and even a cat circus.

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Key West sunsets are amazing at Mallory Square.

Kermit’s Key Lime Pie

At Kermit’s Key Lime Shoppe savor a slice of frozen key lime pie dipped in dark chocolate or any other key lime tastiness. My oldest daughter and I enjoyed it but my youngest said it was good “except for the lime part.” Ah, kids.

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For over 20 years, Kermit’s Key Lime Shoppe has been serving Key West delicious treats.

Cuban Coffee Queen

At the Cuban Coffee Queen sip a cup of dark and rich Cuban coffee and enjoy a sandwich or snack. According to their website, the cafe is dedicated to a woman in Cuba who made the “best coffee.”

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The tiny Cuban Coffee Queen in Key West serves up big coffee flavor.

Though we only had a day in Key West, we enjoyed soaking up its unique vibe and history. There is plenty to see, do, and taste in this southernmost island.

Have you ever been to Key West? How is it special to you? Please share in the comments. Thanks!

Looking for more ideas for family road trips? Read Travel: An Evening in Savannah and Travel: Funky Florida.

Want to plan a trip to or learn more about Key West? Click here to purchase Fodor’s In Focus: Florida Keys and Key West. A portion of your purchase will help maintain my blog. Thank you for your support!


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