At the southern tip of Florida, Key West is a quintessential island town. It’s full of history and quirky island flair. Spending at least a day in Key West is something that should be on everyone’s bucket list.
Of course, you could easily spend more than one day in Key West. But, we know that not everyone has unlimited vacation time. And, getting to Key West is not necessarily easy. So, we’ll focus on how to make the most of just one day.
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Planning Your Key West Trip
Let’s start with some of the logistics of planning a trip to Key West. Yes, you can fly straight to Key West. But, it’ll cost you. And, honestly, the drive through the Florida Keys from Miami to Key West is one of the best drives in the country.
Thus, our recommendation is to fly into Miami, rent a car and make the drive to Key West. In fact, this is exactly what we did when we visited in August 2021. Our long weekend was just enough time to enjoy the trip, though we easily could have enjoyed more time in Key West.
Read Grant’s article on the drive from Miami to Key West.
Another thing to consider when planning your trip to Key West is the time of year. I’m going to be honest, August is just about the worst time to go. Not only is it hot but it is also hurricane season so your trip could easily get canceled or could be very rainy.
We knew booking this trip for August was risky. But, we were looking to use a couple of free night hotel certificates before they expired at the end of August. So, we rolled the dice.
The day we arrived in Key West, Hurricane Ida was passing over Cuba, just 90 miles south. Yes, we did get the very tips of the rain bands and some high winds and waves. Overall, though, it wasn’t bad enough to ruin our day in Key West! Honestly, though, we got lucky.
It’s best to avoid visiting the Keys during hurricane season, if possible.
One Day in Key West
Once you make it to Key West, you’ll find much more to do than just sit on the beach. And, if you’ve only got one day in Key West, we suggest you spend that time exploring. Of course, if you have two or three days, then you should definitely plan to spend time soaking up the sun!
As you tour Key West, you’ll find many references to the fact that it is the southernmost city in the contiguous United States. And, of course, there is a marker noting the Southernmost Point. You’ll find it on the southeastern side of Key West, at the corner of South Street and Whitehead Street.
I would suggest hitting the Southernmost Point early in the day to avoid the long lines of people waiting to get a picture. Or, just forgo the selfie and take a picture of the buoy between the other visitors, as we did!
US 1 Mile Marker 0
At 2,370 miles, US Highway 1 is the longest north-south road in the United States. It runs from Key West, FL to Fort Kent, ME connecting many major cities on the east coast. While it does not hug the coastline for its entire length, it is the only highway through the Florida Keys. As such, you’ll know you’ve arrived in the heart of Key West when you reach Mile Marker 0.
Yes, the location is clearly marked, at the corner of Whitehead Street and Fleming Street. Of course, there are plenty of souvenirs if you are looking for one.
Conch Tour Train
We usually find the tourist trains and trolleys in various towns a bit too, well, touristy. Not in Key West, though. In fact, we highly recommend you take a ride on the Conch Tour Train as one of your first activities in Key West.
The Conch Train is an open-air tram that takes you through the streets of Key West. Along the way, you’ll pass many of Key West’s most popular attractions. Train engineers will narrate the journey, providing information on Old Town Key West and its history.
Tours depart daily from Front Street and make three stops on the 75-minute journey. While it may be a little hokey, we cannot think of a better way to start your day in Key West. It really is a great way to learn about the city.
Ernest Hemingway Home and Museum
One of Key West’s most famous residents was Pulitzer and Nobel Prize winner Ernest Hemingway. Hemingway initially arrived in Key West for a visit that ended up being longer than anticipated. It didn’t take long for him and his second wife to fall in love with the city and decide to make it a permanent home.
The Hemingways bought an 1851 Spanish Colonial-style home, which they spent considerable time and money restoring. Here, Hemingway wrote and enjoyed life, particularly big game sport fishing. He also loved a six-toed cat named Snow White, who was gifted to him by a ship’s captain.
Today, you can visit the Hemingway Home, which is still home to approximately 60 six-toed cats. Some of the cats who live on the grounds are descendants of that original cat. In addition to seeing the cats, you will learn more about Hemingway’s personal and professional life.
Allow 1-1.5 hours for a visit.
Harry S. Truman Little White House
Constructed in 1890 as naval officer’s housing, this building has housed several famous visitors over the years. Most notably, President Harry S. Truman spent 175 days of his presidency here. A visit to the Little White House is a step back in time and a glimpse into American history.
A guided tour through the Little White House will take you through the house and will include the history of the building and some highlights of Truman’s presidency. Visitors can tour the grounds on their own, free of charge.
Allow about 1-1.5 hours for a visit.
Fort Zachary Taylor Historic State Park
Whether you are looking to explore a bit of American history or are just looking for a nice beach, head over to Fort Zachary Taylor Historic State Park. As you might suspect, the park is the southernmost state park in the contiguous United States.
You can tour the brick fort on your own, past cannon and gun ports overlooking the water. Exhibit signs tell about the fort’s history and importance in the Civil War and the Spanish-American War.
After touring the fort, soak up some sun at one of Key West’s best beaches. With sandy shores, shady palm trees and a cafe, this is the perfect beach stop as you enjoy a day in Key West.
Allow 30 minutes to an hour to tour the fort. Spend as much time as you want on the beach.
Set on the western waterfront of historic Key West, Mallory Square is known as the best sunset celebration in Key West. But it is more than just a sunset. During the day, Mallory Square is a center of shopping, attractions and dining.
Two hours before sunset, the party begins, complete with street performers and food vendors. As the sun dives towards the horizon, the sky fills with purples and pinks of sunset. Many consider this the best sunset in the Keys.
Of course, your day in Key West doesn’t end with sunset. Head on over to Duval Street for some of Key West’s best nightlife. Lined with restaurants, bars and shops, Duval Street is a great place to grab dinner, enjoy some after-dinner drinks or just people-watch.
One warning: if you have young kids with you, it might be best to time your stroll along Duval Street for the daylight hours. While Duval isn’t quite as racy as Bourbon Street in New Orleans, it is certainly more appropriate for adults after dark.
Dry Tortugas National Park
If you only have one day in Key West, then you won’t have time to tour the city and visit Dry Tortugas National Park. But, if you have a second or third day, we highly suggest you spend a day visiting the park.
Dry Tortugas NP is located 70 miles west of Key West and is only accessible by boat or seaplane. The 100-square mile park consists of seven small islands and the surrounding shallow waters. The main island houses Fort Jefferson, a Civil War-era fort that was used as a prison.
A ferry trip to Dry Tortugas NP will also include breakfast and lunch, entry into the national park, a narrated tour of Fort Jefferson, and complimentary snorkeling equipment. In addition to touring the fort or snorkeling, you can walk around the beach or just relax in the sun.
If you have the time, you can even spend a night camping at Dry Tortugas NP.
Where to Eat and Drink in Key West
As you might suspect, there is no shortage of great places to eat and drink in Key West. Whether you are looking for a meal, a snack or the island’s famous Key Lime Pie, you certainly won’t go hungry here!
Garbo’s Grill started as a tiny little food cart on a street corner. Today, it’s a full-fledged food truck with a permanent location behind Hank’s Saloon on Caroline Street. The menu consists of tacos, burritos, burgers and dogs, all served with a Caribbean flair.
The Korean BBQ and Cayo Fish tacos both consisted of the perfect mix of seasoning and toppings. Of course, we topped it off with a beer and a mixed drink from the bar.
There really isn’t a better lunch than this in Key West.
Captain Tony’s Saloon
Captain Tony’s Saloon is easily Grant’s favorite dive bar in Key West. Located in the original spot of Sloppy Joe’s, this dingy bar has tasty drinks and live music.
The owner, Tony Tarracino, had lived a ton of lives. He started out working for the Mob in New Jersey, before moving to Key West, where he worked as a shrimper, charter boat captain and gunrunner before starting his saloon in 1961. He even ran for mayor of Key West several times before being elected in 1989.
He saw countless musicians come through his bar but one caught his eye and later took off as a star. His name was Jimmy Buffett, who immortalized both Tony and his bar in the tune “Last Mango in Paris.”
I went down to Captain Tony’s
To get out of the heat
Then I heard a voice call out to me
‘Son, come have a seat’
I had to search my memory
As I looked into those eyes
Our lives change like the weather
But a legend never dies
He said I ate the last mango in ParisJimmy Buffett – “Last Mango in Paris”
Took the last plane out of Saigon
Took the first fast boat to China
And Jimmy there’s still so much to be done
For traditional Key West cuisine, we headed over to Mangoes on Duval Street. With a large open-air porch and bar, it really was the perfect setting for a late dinner. The fantastic food and drinks just topped off our evening.
We started with Grant’s favorite Key West appetizer of Conch Fritters. For entrees, we chose the Yellowtail Snapper and Blackened Cobia. Of course, no dinner in Key West is complete without a slice of Key Lime Pie.
The mixed drinks were fantastic as well: the class Pilar Blonde mojito was perfect and Grant really enjoyed the Spicy Mexican Mule, made with Pineapple Jalapeño Tequila.
If you’re looking for a good dinner on Duval Street, we recommend Mangoes for food, drinks and ambiance.
Clemente’s Trolley Pizzeria
If I’m being honest, I would not have had expected to eat at a pizza joint in Key West. We tend to choose more local flavors when traveling. But, we ended up at Clemente’s after arriving on our first night and were suitably impressed by our meal.
We ordered the sausage pizza, which is dusted with pecorino. All I can say is YUM! The brick-oven fired pizza was cooked perfectly, with flavorful sausage and melty cheese. A Key Lime cannoli for dessert was a perfect finish to the meal.
The restaurant is fairly small but it is certainly worth the wait.
Where to Stay in Key West
Even if you only have one day in Key West, you certainly should plan to spend a night or two. The drive from Miami, or even the Upper Keys, is a nice one and you want to have time to enjoy it. Plus, one day is already not quite enough time to really enjoy all that Key West has to offer.
As you might expect, there is no lack of places to stay in Key West. You’ll find the major chain hotels, local hotels and resorts, bed & breakfasts and, of course, vacation rentals. There are even a few campgrounds if you are interested in taking your RV or a tent.
Casa Marina Key West
On our most recent visit to Key West, we made use of two free night certificates from Hilton. As such, we stayed at the Casa Marina Key West, A Waldorf Astoria Resort. Our goal when using a free night certificate is to find a hotel that we could not afford to pay cash for.
I believe the room we booked was worth at least $500/night. And then we got upgraded to an Oceanview room. Yes, having automatic Diamond status with the Hilton Aspire credit card definitely has its perks!
The hotel is located right on the beach on the south side of Key West. In fact, it’s not far from the Southernmost Point. If you are interested in spending some time relaxing on the beach or by the pool, this is a great option!
Dating back to 1920, the hotel was once a hideaway for Old Hollywood’s elite. Now, it houses Key West’s largest private beach. We stayed in the Historic Flagler Building and I have to admit, our room felt historic. Still, we enjoyed our stay and the outdoor space certainly made up for the lack of modern touches in our room.
DoubleTree Resort by Hilton
On a previous trip, we spent one night at the DoubleTree Resort by Hilton. This hotel is not waterfront but is certainly a more affordable option when staying in Key West. As a resort, you’ll find a nice outdoor space around the pool, including the Gumbo Limbo Tiki Bar.
Your resort fee includes internet access, shuttle service to the airport and downtown, access to Sunset Watersport Beach club and more.
Boyd’s Key West Campground
The first thing to know about camping in Key West is that it is not inexpensive. That is especially true if you are looking for a waterfront campsite. But, enjoying the warm salt air from the steps of your RV or tent is a great experience.
In terms of amenities and location, you can’t go wrong with Boyd’s Key West Campground. You can choose from waterfront, dockside, or inland campsites with full hookups. Tent campers can choose from primitive sites or water and electric hookups.
Amenities include a pool and poolside tiki hut, game room, kayak and paddleboard rentals, and more. You are sure to enjoy the well-manicured landscaping and walking paths throughout the campground.
Yes, it’s pricey, with full hookup sites starting at about $100/night but it is an experience you are sure to enjoy. And, let’s honest, it’s still cheaper than most hotel rooms on the island.
Final Thoughts on Key West
Key West is one of those towns that everyone should visit at least once. Yes, it’s a tourist destination and a beach town but it’s also full of history. In fact, there’s much more to do in Key West than in most other beach towns.
With one day in Key West, you can learn about its varied history, including why it’s called the Conch Republic, enjoy some fantastic food and drinks, soak up some sun and enjoy a fabulous sunset. If you have more time, check out more of the local attractions, such as the Key West Butterfly and Nature Conservatory, the Key West Lighthouse or the Aquarium. A day trip out to Dry Tortugas National Park will reward you with even more history and some great snorkeling.
Whatever your interests, you’re sure to find something to enjoy in Key West.
We use Skyscanner to find deals on flights. Skyscanner has a great interface and compares tons of airlines for the best pricing and routing. That said, it does not always have every airline and some airlines will have better deals on their website. Still, Skyscanner is a great place to start.
Click here to search for a flight.
We typically stay at Hilton properties, so we use the Hilton website. You can find good Hilton Honors discounts or AAA discounts for a hotel there. We make great use of our free night certificates from our Hilton Honors American Express.
Click here to book a Hilton property.
If there are no Hilton properties available, we use TripAdvisor to read reviews and book the hotel. We find we can get the best price that way.
Click here to search for a hotel.
We use Vrbo for the times when we have rented a cabin for a weekend getaway, like this cabin in Townsend, TN, or needed to rent a house for a large family vacation. We had a great experience with them in terms of refunding deposits when COVID hit and will continue to use them.
Click here to search for a vacation rental.
As a general rule, we book with Hertz for rental cars. We have had nothing but good experiences with them. Plus, we really like unlimited mileage and not worrying about crossing state lines. We have even rented from Hertz overseas in both Slovenia and Croatia.
Click here to book a rental car.
We have found some amazing prices booking a cruise through Cruise Direct. We have saved a lot of money on our cruises compared to what we found elsewhere, making a last-minute Bahamas cruise even cheaper.
Click here to book a cruise.
We highly recommend Outdoorsy for RV rentals. We rented a camper van for a week to visit Rocky Mountain National Park for the elk rut and Custer State Park for the Buffalo Round-Up and had a blast. The program was easy to use and we really enjoyed the freedom of having a camper van for that trip.
Click here to rent an RV.
We don’t often book tours. Typically, we like to do stuff on our own. That said, there are some experiences you just can’t have any other way. So, when we do want to book a tour, we always check Viatour first.
Click here to book a tour.
We make extensive use of both Good Sam and AAA on the road. Good Sam is normally regarded as a discount card for RVers at campgrounds and Camping World but anyone can use the 5 cents off a gallon at the pump at both Pilot and Flying J.
Click here to get a Good Sam membership.
We have had AAA as long as we have been married and it has more than paid for itself in discounts at hotels, aside from the peace of mind of having roadside assistance. Add in paper maps and the ability to get an international driver’s license and it is more than worth it for any traveler out there.