How to Best Spend a Day in Key West

Key West, Florida - Ship wreck in the main square surrounded by colorful buildings and palm trees

Key West, the southernmost point in the United States, offers the perfect mix of sandy beaches, vibrant culture, and fun nightlife. Spending one day in Key West is nowhere near enough time, but you can certainly make the time you have into a wonderful adventure.

Due to strong winds, we found ourselves with an unexpected free day in Key West. We had originally scheduled a day trip to Dry Tortugas National Park, excited to explore Fort Jefferson and snorkel in the blue waters. However, upon check in we were offered a refund as the ride to the fort would have been quite choppy and no snorkeling was allowed. While disappointed not to explore this less-visited National Park, we were quite excited to have a day to explore Key West. This guide provides suggestions of the best things to do if you only have a day in this beautiful place.

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24 North Hotel - Key West

Where to Stay in Key West:

While Key West is only 7.2 square miles, there are plenty of lodging options from popular hotel brands to adorable B&Bs.

Sam and I arrived in Key West the evening before we were due to head to Dry Tortugas National Park, traveling about four hours from our hotel near Fort Lauderdale. We spent the night at a great hotel, 24 North Hotel. With the temperature chilly and very windy, we did not get a chance to try out the glistening pool, but we did grab a drink at the outdoor Toasted Coconut Bar. The rooms were a bit run-down, but cozy and the price for the night couldn’t be beat.

Depending on what you are looking for, consider staying at a Marriott property near the water with a gorgeous pool, or book a decorated Airbnb near Duval Street where you’ll be near the center of the island.

How to Get to Key West:

Surprisingly, there are several ways to get to Key West depending on your preferred mode of transport. If you are roadtripping within the United States, the Overseas Highway will take you the 113 miles through the Florida Keys to Key West. The drive takes approximately four hours one way, but there are numerous wonderful stops along the way.

If you prefer to fly, consider flying into the Key West International Airport, eliminating the need for a rental while visiting Key West. Airlines like Delta, American, and United fly directly to Key West. If you’re looking for a cheaper options, consider flying into Fort Lauderdale – Hollywood International Airport or Miami International Airport and driving the Overseas Highway to Key West.

A unique way to get to Key West is via the Key West Express via a jet-powered catamaran. The boats leave from Fort Meyers and Marco Island and takes about four hours, and pets are allowed for an additional fee.

Ways to Explore Key West:

Key West by Foot:

We started the day at Ferry Terminal for the Yankee Freedom, which would have taken us out to Dry Tortugas. After cancelling the day trip, we ate a quick breakfast we had packed for the ferry ride and walked along the water. Since Key West is known for its nightlife, it stays pretty quiet in the morning hours. We had the streets mostly to ourselves aside from the occasional runner or walker as we explored Mallory Square, the Sculpture Garden, the Truman Little White House and all of the unique buildings and green spaces Key West has to offer.

Key West Exploring

Mallory Square was quite literally a giant, empty square on the water. Every evening it houses a Sunset Celebration where visitors gather to see local vendors, musicians, arts, and more. However, during the morning hours the square was almost empty, except for several individuals calling the square home. A humble reminder that for all the splendid things Key West offers, there are people barely getting by.

Key West by Bike: 

After walking almost 3 miles before 10am, Sam and I decided bikes were a must to really get the full Key West experience. There are several places that offer bike rentals and if you are staying in Key West, your hotel or resort likely offers bike rentals. While walking back to get sub-par breakfast at Harpoon Harry’s, we happened upon a bike rental shop, WeCycle and rented two single-speed cruisers for the day. I highly recommend bikes for your visit as you can get around so much easier, but you must use caution as cars are zooming around you. And don’t forget to watch out for the roaming roosters that are famous in Key West!

Fort Zachary Taylor Historic State Park:

By mid-morning the sun had finally peaked through and it had warmed up quite a bit. I was itching for some beach time so we hopped on our bikes and headed towards Fort Zachary Taylor Historic State Park. The park entrance fee is $7 per vehicle or $2.50 per person if arriving on foot or bike. The park provided great options for both myself and Sam as it had a great beach area and also had the fort area and some hiking trails.

Fort Zachary Taylor State Park

The beach area included a small gift shop, concessions, and beach rentals (snorkels, chairs, umbrellas). There were also bathrooms and changing facilities. I spent four hours at the beach – it was so relaxing! Sam spent a little bit of time exploring the trails, but we both decided to save the fort for our next trip to Key West!

Even with the colder weather, the beach had gathered a small crowd by early afternoon. The beach area was great and the water was beautiful, but the shore was a bit rocky, making it somewhat difficult to enter the water. Not to mention, the water was freezing!

Southernmost Point, Kind of? 

On the way back to drop off our bikes, we made a stop at the Southernmost Point. Okay, I know it is not technically the Southernmost Point of the United States, or even of the lower 48 states, but we were so close to the unofficial point we had to make a stop.

Southernmost Point - Key West

There was a decent-sized line to get a photo with the buoy, so I snapped a solo-buoy photo before realizing I was standing next to this guy with a super cool bike. Turns out, this guy had just completed his months-long bike ride from Washington to Key West. He gave Sam some tips on how to prepare for a long bike ride and we left him to celebrate the completion of his journey.

Duval Street:

After returning our bikes, I was excited to hit up Duval Street for a mini bar crawl. Earlier in the day we had passed a bar with a balcony and Sam was hooked. That was stop one!

On the way up to the second floor porch, we heard that there were actually three bars – The Bull, Whistle Bar, and Garden of Eden. I decided to check out the third floor while Sam ordered our drinks. I should have bought that round. Turns out third floor is clothing optional, hence the no photography and no sex on premises signs. I got to the third floor and was a bit surprised to see a man taking off his towel to reveal his man parts. I quickly made my way back downstairs. Needless to say, there is something for everyone at that bar. We thoroughly enjoyed the second floor as we sat outside and people-watched while overlooking Duval Street.

Duval Street

Next up was Fogarty’s Restaurant & the Flying Monkeys Saloon, right across the street from Whistle Bar. Here we enjoyed a drink and a delicious house salad with grilled chicken. Although I’m not much of a hard-liquor drinker, this place had just about any frozen drink you could ask for. They also offered a virgin option as well.

After some food, I was more than ready for dessert. On the next block over we found ourselves a Hard Rock Café that was very empty – I needed to sit inside as the wind was picking up. The Banana-Split Sundae was AMAZING! I stuffed myself with more calories than I even want to think about (totally worth it!) and Sam and I reflected on the wonderful day we had.

Post-banana-split I was ready to slip into a sugar coma so we hit the road and headed back to the Fort Lauderdale Area.

Overall Impression:

I highly recommend a stop in Key West. From our pre-trip research, Sam and I weren’t expecting much from Key West, but we were quickly persuaded that more than a day should be allotted to truly experience all that Key West has to offer! I loved the lively atmosphere of Duval Street paralleled with the relaxing environment at the beach. Make sure to check out my posts on Jekyll Island, GA and Tampa, FL for additional awesome beach destinations.

Happy Travels! 



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