A 1-Day Itinerary for Key West, FL for an Unforgettable Trip
Key West has an atmosphere all of its own. From the beautiful “gingerbread” houses to the resident “feral” chickens, there is a lot to see that is unique to Key West.
How To Spend One Day in Key West
- Check out Hemingway House and Museum
Ernest Hemingway lived in Key West for many years. A fun fact is that his swimming pool was the first personal use pool built in Key West. You can see it by visiting the Hemingway House and Museum in Old Town on Whitehead Street. Another fun aspect is that more than 60 cats – descendants of Hemingway’s six-toed cat given to him by a ship captain – now live on the grounds of the estate. Some of the grand kitties even have six toes, too!
While at the Hemingway House and Museum, you can see the location that motivated Hemingway to write “The Old Man and the Sea.”
The museum and house are open daily at 9am and have an admission fee. - Visit Key West Lighthouse
Across the street from the Hemingway House is the Key West Lighthouse. If you climb the 88 steps to the top, you’ll have a great view of Key West; the lighthouse dates back to the mid-1800s and is more than 80 feet high.
Don’t miss touring the museum where the lighthouse keeper used to live. It tells the story of how the lighthouse saved many ships from wrecking on the reefs and put the pirates who looted the wrecks out of business.
- Walk along Duval Street and do some window shopping
The famous Duval Street is the center of activity in Key West. Grab some lunch here after your morning activities and then get ready to explore.
In addition to great window shopping, street performers, and people-watching (you will see it all), the majority of the bars and a handful of the restaurants (such as Sloppy Joe’s) have free live entertainment at all hours of the day and night.
So meander down Duval Street and enjoy the atmosphere. If you get tired or hot, just pop into any of the open-air bars (all with the A/C blasting and the windows open), order a drink or a soda, and enjoy the action of Key West! - Enjoy the Sunset at Mallory Square
In the Keys, it seems everything is celebrated…and at Mallory Square, they celebrate the sunset every night. As sunset approaches, thousands of people make their way to the historic Mallory Square (historically Mallory Docks) to watch the amazing sunset.
In addition to the breathtaking view, there are numerous street performers that are worth seeing, including traditional mimes, jugglers, and musicians, there are normally glass walkers, escape artists, trained cats, tight-rope-walking dogs, sword swallowers, etc. It is truly a can’t-miss experience.
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Other Fun Things To Do In Key West When You’re Short On Time
Southernmost Point and House
Since Key West is the southernmost of all the Florida Keys and the US, there’s a buoy that declares this to be true. In fact, Key West is actually closer to Cuba than to Miami.
There’s also a hotel that is said to be the southernmost house in the US. This house, built in 1896, is aptly called Southernmost House Grand Hotel & Museum. Although there are supposedly other houses more southern than this one, and also a military base, it was southernmost for a long, long time and so retains the name. The house is very lovely and much-photographed. If you want to stay there, the hotel rooms are quite pricey, but of course, guests are paying to stay at the southernmost point in the US.
Dry Tortugas National Park
During a visit to Key West, nature lovers can visit the Dry Tortugas National Park, located roughly 70 miles west of Key West. This unique national park consists of seven small islands.
You have to take a boat or seaplane to reach this remote park. Once there, spend the day bird-watching or snorkeling. Also located within the park is Fort Jefferson, which was built in the mid-1800s to protect trade in the Gulf of Mexico.
Conch Tour Train
Key West is a city rich in history. It was at one time the richest city in the United States (due to the many shipwrecks in the area) and has thrived in many different industries, such as producing cigars and cultivating sponges. To learn about the history of this fascinating island, a good place to begin is by taking a tour on the Conch Tour Train.
Tour guides provide an entertaining and lively history of the area that includes information about Ernest Hemingway (one of the most famous residents), marine history (pirates once freely roamed the seas), and the earliest inhabitants of the area (who gave Key West its name).
Another Tour Option: If the supernatural interests you, another tour, The Ghosts and Legends of Key West Tour, might also catch your fancy. This 90-minute tour relates the stories of haunted houses in the area and spins legends of pirates and voodoo from the area.
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How To Enjoy The Water In Key West
Key West Water Sports
Many couples go to Key West to enjoy water sports, both on and under the water. Boating is popular; you can take your own boat, charter one, or pay admission to ride on some. Sail on a catamaran, look at the amazing sea creatures and coral reefs underneath you on a glass-bottom boat, or charter a fishing boat for a deep-sea adventure. Take a boat out to go snorkeling or scuba diving on the reefs or out to the Dry Tortugas.
Key West may not have the white sand beaches the rest of Florida is known for, but there are still many good experiences to be had in the ocean and the gulf.
If the great outdoors is more your forte, Key West will not disappoint. Kayak the waters surrounding Key West on a guided tour. Jet ski in the Gulf of Mexico. View dolphins swimming in the wild from a charter boat. You can also snorkel in the waters of the Atlantic Ocean, enjoy marine life, or explore shipwrecks. If you want to see the abundant sea life but don’t want to get wet, take a glass-bottom boat tour of the waters surrounding the island.
Key West Fishing
Fishing in Key West is world-famous. Charters are available for both deep-sea or backcountry fishing or bring your own boat. The deep-sea fisherman might angle for barracuda, sailfish, or blackfin tuna while the backcountry fisherman might hope to catch bonefish or tarpon.
Be Your Own Tour Guide
Still not sure how to spend your perfect day in Key West? Be your own tour guide and see where the day leads you! There are free maps of Key West located in many of the businesses in Key West that map out the majority of the attractions and historic sites in Key West.
Pick one up and be your own guide on a walking tour of Key West. There are many unique homes and historic buildings in Key West including the Hemingway House, the Truman White House, the old customs office, and Fort Zachary Taylor to name a few. Other great sites and photo opportunities include Mile Marker 0 on US 1, the Southernmost Point, and the Statue Garden.
Enjoy Your Day in Key West, Florida!
Key West has many fun things for you to do; if you like the sun, the ocean, and a laid-back atmosphere, it’s the place for you. The weather’s usually nice, the people there are friendly, and there are lots of fun activities you can enjoy together.
And even better for travelers, Key West is a city where you can have a great time on any budget. While it is easy to spend big bucks while you are there are also a lot of activities that you can do that are free.
