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Sunset Pier in Key West, Florida

Things to do in Key West with Kids

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On a thin strip of land settled at the end of a long stretch of roadway where ocean waters is all the eye can see, is a place filled with village like charm, Caribbean flair, and literary influence.  I’m talking about Key West.


With a little preparation, Key West is an easy day trip from Hilton Key Largo Resort.  Like many locations in the keys, it’s a straight southwestern shot down the Florida Keys Overseas Highway, just a two hour drive to what will make you feel like you’re standing on the edge of the earth.  Here are a couple of tips to ensure that you’re able to optimize your time in the area. These are especially good practices if you’re traveling during a high tourist season and you only have one day to devote to the area.

1. Plan to Leave early

A boating, diving, and beach-going haven, weekends draw throngs of water enthusiasts to the keys. This situation can quickly clog up the largely two-lane (one direction in and one direction out) Overseas Highway with traffic that includes slow moving vehicles toting boats. Leaving early can mean less time spent sitting in traffic with your blood boiling.

2. Secure a bike rental

Congested streets and often limited parking make traveling via bicycle the most efficient way to cover a lot of ground in Key West.   My family had a great experience with Island Bicycles.  Not only was the rental affordable, the staff was thorough and knowledgeable.  Each of our bikes was adjusted accordingly and some of those adjustments tweaked further after a technician watched while we each took a spin around the bike shop parking lot.

We even received an education on bike terms as it turns out there was one in particular we were misusing.  We thought we needed a bike trailer for your youngest child.  What we really needed was called a, “Tug-a-Bug.”  This is a youth bicycle that can be attached to an adult bike making it a bicycle built for two.  A Tug-a-Bug has no front tire, only a rear one.  It is a great contraption to have when cycling with a kid who is old enough to forgo training wheels but does not have the speed or dexterity to keep up with the rest of the family just yet. Book ahead, on weekends bike rentals can quickly sell out!

3. Do Your Research, then Pick and Choose

There’s a lot to see in Key West.  If you have only a day to take in the sights, you will need to pick and choose because there won’t be time for everything.  In the end, my family went with a selection of places that gave us a nice overview and left us wanting to come back and see more.


Key West’s unique architecture will be your first indication that you’ve arrived in the right place.  This key has street after street of gingerbread mansions, conch houses (wooden homes set on posts or piers which allow air to circulate under the floor) and simple shotgun style homes lovingly preserved by their occupants.


One of the most famous homes drawing visitors to the area is that of American author Ernest Hemingway.  A two-story New Orleans romantic style colonial, the Hemingway Home was occupied by the author, his wife and sons for nearly a decade. Despite being filled with art, photographs, and many other pieces of memorabilia connected to the author, it is not difficult to imagine raising children here.  The grounds are spacious enough for there to be bikes and toys strewn in them just like in any other yard where children live.  There are also lots of cats. Hemingway loved cats and apparently some the current feline residents of the home are direct descendants of one of his kittens.

When you consider that he wrote The Snows of Kilimanjaro and other short stories from the writing studio behind the house, the ordinariness of this home is pretty striking as is the intimacy of the tour itself.  Not much is roped off here so you can actually stand in Hemingway’s living room, bedroom and other parts of the home, as if you are a family member or an invited house guest.

If you’re interested in going, I’d advise that you either wait until the kids are old enough to appreciate the works of Hemingway or that you introduce them to him beforehand otherwise you might be in for an exchange like the one I had with my daughter, a sixth grader at the time.

“What did this guy write, Mom?”
A Moveable Feast
“He wrote about take out?”
“No child, that book is about Paris!”
“Hmmm… I did not get that from the title.”

Ernest Hemingway's house in Key West.

Ernest Hemingway’s house in Key West.


Located just a short walk from the Hemingway home is the lively Duval Street.  Outdoor cafes, galleries, bodegas, and cigar shops hint at the street’s long time Cuban and other Caribbean influences as does the colorful architecture. By day the area offers family-friendly and fun shopping and dining experiences.  By night though, a vibrant and more adult carnival atmosphere emerges and often goes on until morning.

Duval Street, Key West

Duval Street is a lively shopping experience filled with Cuban and Caribbean influences.

Not far from the Duval Street you’ll find the Southernmost Point of the Continental United States. It isn’t difficult to spot the giant red, yellow and black marker that lets all who pass by know they are 90 miles from Cuba. If you don’t see it immediately, it could be because there are so many people around it.  On the day my family visited, there was a line stretching for blocks and loaded with folks wanting this marker as a backdrop for a group photo. Immediately we opted to move on, motivated by the fact that our children threatened to stage a boycott on good behavior if we didn’t!

Here are a few options for grabbing this photo opportunity without standing in line:

  1. Forget about the family portrait style picture and snap the monument quickly as one group exits and before the other step up for its turn.
  2. If the family portrait is an important keepsake for you, then arrive early ahead of the crowds to get your photo.
  3. Pick up a Christmas ornament and take a miniature version of this marker home with you.  They can be found in multiple shops in and around Duval Street.


As the sun begins its descent, street performers, artists, craftsmen, and food vendors take over Mallory Square and a sunset celebration commences. This funky street party takes place nightly all year round (weather permitting) and because it is intended to be impromptu (meaning never planned), you could encounter a different kind of party here each night. My family enjoyed magic tricks, juggling, comedy, and fire eaters and dancers along with an array of musical groups.  Sunset Celebrations begin two hours before sunset and end two hours afterward.


Before you head over to the Mallory Square celebration, my family highly recommends that you try to get a table near the water’s edge on Sunset Pier.  The sunset here is dazzling (hence the name of the place) and the constant parade of boats of all shapes, sizes, and motor power making their way into the marina is quite a sight to see!  We spotted vessels ranging from a lone boat with only one couple aboard to an obviously pricey yacht to a flotilla of sailboats and a packed party boat brimming with music and song. The color burst produced by the sunset provided a fantastic backdrop for this floating party.


As the historic story goes, Ponce de Leon and fellow Spaniard Antonio de Herrera set a course toward Florida in 1513 in search of the Fountain of Youth. They never found the fountain but maybe that was because that elusive Fountain of Youth came in a different form — the Florida Keys themselves. And from what my family saw, youthful fun is alive and well in Key West.

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Kristine lives in Mountain View, California, where she is the mother of a gifted girl athlete and a special needs charmer. Like almost everything in her house,…

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