Walgreens Key West, Strand Theater

How to Spend One Day in Key West

(Last Updated On: December 15, 2019)

For as long as I can remember, I have always wanted to spend one day in Key West. A visit to this beach paradise meant relaxation, sunshine and fun.

Key West is the laid back southern most part of the United States. It is situated just 90 miles from Cuba and has always held a reputation in my mind as a laid back beach town.

I imagine a place where people can get around by the ease of a one speed bicycle.

Bikes on sidewalk - Key West

Last February my husband and I took our first cruise together that left from Fort Lauderdale, Florida.

(Check out my post on What You Need To Prepare For A Cruise Vacation.) On our last day of the cruise we arrived back to the Ft. Lauderdale cruise terminal at 7:00 AM and we had planned on driving to Key West.

After all, our plane back to Portland, Oregon was not departing from Miami until 10:00 PM that evening.

Plenty of time to make the two and a half drive south to Key West we thought to ourselves.

With a car rental reserved at the Miami airport, just about 25 minutes from Ft. Lauderdale we figured we had this last day of our vacation planned out perfectly.

Long story short, everything took longer than expected on that last day of our vacation.

Our cruise ship was at the terminal at 7:00 AM but we did not get off the boat until about 8:00 AM.

We had booked a shuttle service through the Holland America cruise line to take us to the Miami airport from the Ft. Lauderdale terminal and that also took longer than we thought to depart.

When all was said and done, by the time we got our rental car in Miami it was almost 11:00 AM.

Cool Van in Key West

Mileage wise the trip from Miami to Key West should only take about two and a half hours.

But, the truth is it takes way longer. That’s because the road through the Florida Keys is at mostly a single lane with slower speed limits, the trip was taking far longer.

We made it as far as Islamorada, Florida. Islamorada is about halfway to Key West before deciding to turn the car around and head back to Miami.

Fast forward a year later to January 2019…

It’s redemption time! We had another week long cruise vacation planned through the western Caribbean and the first cruise stop was, you guessed it, Key West!

I must say that Key West exceeded my expectations and I would happily book a vacation in the future there.

If your time is limited, as mine was, here is what you can see and do if you only have one day to spend in Key West, Florida.

Stroll Duval Street

Duval St. is the main drag of Key West. This is where you will find most of the restaurants, cafes, clothing stores, gift shops and bars.

By walking through Duval St. as one of the first things you do in Key West will help you get the “lay of the land”.

Walgreens Key West, Strand Theater
The prettiest Wallgreens you will ever see. Located in the historic Strand theatre on Duval St. Key West

Visit the Southern Most Point

A trip to Key West is not complete if you don’t visit the monument representing the southern most point in the continental United States. Is it touristy, sure, but you just have to visit it!

Don’t be alarmed if you see a line that wraps around the street.

It is very common to have a long line at this attraction. You will notice anxious shutterbugs awaiting their turn to take selfies with the southern most point buoy. But, the line moves quickly.

If its a hot and humid day, which is likely, grab yourself a fresh coconut water from the nearby vendor.

Southern Most Point Key West

Visit Ernest Hemingway’s Home

Whether you are a literary buff or not everyone will enjoy visiting the home of Nobel Prize winner and author Ernest Hemingway.

No reservations are needed to tour this immaculate home.

Simply show up, its doors are open 365 days a year. Admission is cash only and tours last about 30 minutes.

Ernest Hemingway's Home - Key West

Visit the Smallest Bar in Key West

So, it doesn’t win the title of smallest bar in the world…but it’s close. The Smallest Bar is just 72 square feet located right on the bustling Duval Street.

It can claim the title of smallest bar in Key West, and that alone seems to attract a wide audience. With only a few bar stools available this place is more of a stop by, take a shot of vodka and move on sort of venue.

Smallest Bar Key West

Ride a Bike, Vespa or Golf Cart

Key West is fairly easy to get around. At just over seven square miles its easy to explore on foot, but its more fun wheels! No matter where you stroll in Key West you will find rental shops ready to lend a fun bike, vespa or golf cart for your exploring pleasure.

One spot that is known for its good prices on rentals is:

Tropical Rent A Car on Duval Street. But don’t let the name fool you, they have more than cars. You can rent bikes, scooters and electric cars that are more like golf carts.


Visit Mallory Square & Boardwalk

Mallory Square and the nearby boardwalk lined with restaurants, shops, breweries and souvenirs is a fun place to enjoy the evening and sunset. Mallory Square is particularly known for its crowds that come to watch the sunset every night while street performers juggle and dance.

Downtown Key West

Visit Key West’s Oldest Lighthouse

Enjoy stunning views from the top of the 65 foot Key West Lighthouse. Completed back in 1825, this makes the Key West Lighthouse the oldest in town. For a small admission fee of $10 you can climb the 80 steps to the top of the lighthouse and delight in the birds eye view of the entire town.

Try Key Lime Pie

In my opinion, tasting key lime pie in Key West is a must do activity. You will find that just about every restaurant and bakery in town has key lime pie on the menu. But if you want to try the the most famous spot in town go to Kermit’s Key West Lime Shoppe located on 200 Elizabeth St. This is located in the heart of downtown just a few blocks from Duval St.

Kermit's Key West

I hope you are inspired to visit Key West and try some of these fun things to see, do and eat! I will leave you with a short video that highlights some of these activities from my recent trip. Bon voyage!


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