In 2017 we booked a long weekend trip to Key West. Then Hurricane Irma happened just a few months before our visit. The category 4 made landfall 20 miles east of Key West before churning through pretty much all of Florida.

I’m not gonna lie, I was a little apprehensive to go, not sure what we would find. But our vacation rental company said their homes sustained no damage and the island fared well.

And if anything, I figured our presence would be beneficial to the businesses and the people who make their living off tourism. Which is a lot. According to the Sun Sentinel, tourism accounts for more than half of all jobs in Monroe County. And 60% of the money spent there comes from tourists, according to numbers from the county’s Tourism Development Council.

Long story short.. it was a great decision. Key West was still kickin’ and looked great. And it’s a great place for a family-friendly vacation, with lots of affordable things to do. Check out some of these reasons why.

I received free passes to some Key West attractions thanks to Historic Tours of America. All opinions are authentic and my own.


Old Town Trolley

I highly suggest kicking off your trip with a ride on the Old Town Trolley.

The hour and a half trip all around the island gives a glimpse into the fascinating history of this nearly 200-year-old town.. from shipwreck salvaging to famous authors.. and even a few ghost stories. And you get to see a lot of the island’s gorgeous architecture.

It’s also a really great way to get around town. You can hop on and off all day so you can explore the different stops up close. And you can get back on a second day for a discount.

Hemingway Home

This was what I was looking most forward to during our trip because I am a big fan of Hemingway. And the tour of his Key West home did not disappoint. Being in the place where he wrote most of his iconic novels, was thrilling.

And the tour guide was so knowledgeable and kind, letting my kids feed the famous Hemingway cats.

*Be sure to take cash to the Hemingway Museum. They currently only take cash at the front entrance. But you can pay with credit cards in the gift shop.

Truman’s Little White House

Along with Hemingway, one of the other men most responsible for spurring modern tourism in Key West was President Harry Truman.

Taking 11 trips to Key West while in office, Truman saw the island as a relaxing retreat, but he also conducted a lot of business there too.

The tour of where Truman stayed, and where other presidents have stayed after him, was fascinating.

Shipwreck Museum

Talk about a colorful history! This museum illustrates how Key West grew to be the richest town in America at one time.. built on the gold and treasures from hundreds of ships that wrecked off the reef that barriers the Florida Keys.

And the role-playing tour guide really brings the history to life, making this a fascinating stop for the whole family.

Free Sights

Mallory Square Sunset

Key West offers amazing sites from sun up to sun down. And the best place to be when the sun goes down is Mallory Square.

When the sky over the ocean lights up with gorgeous amber colors, the square comes alive with performers and vendors.

Southernmost Point

You can’t leave town without stopping at one of Key West’s most famous selfie spots. The Southernmost Point buoy was a little worn from Hurricane Irma and in the middle of a repaint when we visited. But it was still exciting to be standing at the southernmost point in the U.S. and just 90 miles from Cuba.


There are so many awesome things to do in Key West, I wish we’d had a whole week to do them.

Here are some other attractions provided by The Florida Keys & Key West. Check out their website for lots of great ideas and resources.

Florida Keys Eco-Discovery Center – Visitors will take a journey into the world of the native plants and animals of the Keys, both on land and underwater. The center features over 6,000 square feet of interactive and dynamic exhibits including a mock-up of Aquarius, the world’s only underwater ocean laboratory.

The Key West Butterfly and Nature Conservatory – Walk through an inviting environment filled with hundreds of the most beautiful winged creatures in nature. Guests will discover an impressive collection of flowering plans, colorful birds, cascading waterfalls and trees that set the stage for the “flowers of the sky.” Attractions also include a learning center where guests can explore butterfly anatomy, physiology, lifecycle, feeding and the migratory world of the monarch.

Don’t Forget…

A few things you want to make sure you have with you while exploring Key West include the obvious.. water, good shoes, sunscreen, a camera and a map.

And a few things you might not think of.. like cashAll of the tour guides we met while exploring the museums and attractions were so knowledgeable, dedicated and kind. And they accept tips, which they all so greatly deserve.

Also, if you catch the sunset at Mallory Square you’ll want to tip the amazing performers and maybe buy a beautiful handmade trinket.

You might also want a bicycle. The island isn’t that big and neither are the streets. Free street parking can be hard to find and lot parking isn’t cheap. Popular modes of transportation around the island are bicycles and scooters. If you can’t bring your own there are plenty to rent.

And you’ll need a bag for all your souvenirs. From ‘Mile 0’ stickers and Conch Republic flags to Hemingway novels and Sloppy Joe’s t-shirts.. you’ll want to take home lots of island paraphernalia.

I hope you get to visit soon!

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