Free Self-Guided Walking Tour of Key West
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Key West, Florida is a small 7-sq mile island in the Florida Keys archipelago. It is home to the southern-most point of the continental US, residences of famous Americans, beautiful pastel Caribbean-style homes, dozens of bars on the famous Duval Street, and great beaches and snorkeling spots. Due to its small size and high density of sights, it is an extremely walkable city. We arrived in Key West via Cruise ship which docks right in the center, perfect for a fun (and completely free) day of exploring this eccentric island.
Key West Art & Historical Society Museum
The cruise ship docks right outside of the Key West Art & Historical Society Museum, which is a great place to start. The museum includes details of the history of Key West including wreckers that made fortunes from recovering sunken ships in the area, the Navy's occupancy of Key West, its prohibition days, and famous paintings and statues. The museum's building was once the customs house for the island. Entry to the museum is $10 for adults. If you want to skip out on the history, the outside of this historical 1891 red-brick building and the giant iconic kissing couple statue is still a must see.
The Harry S Truman Little White House
While president, Harry Truman vacationed down in Key West and used this provisional White House for meetings and official work. Since it has been used by many subsequent presidents during working vacations with their families. Feel free to read the sign below for all of the significant events that occurred at this location. I graduated from his namesake university, so I have a special love for Truman.
You can get a tour of the house for $20, but we just stopped by to see the outside of the house. The home is located in an affluent neighborhood of other gorgeous white houses with colorful window shutters and accents.
Mile Marker 0
Head to the end of the road next. Or the Mile 0 marker sign of US Highway 1. If you were to follow Highway 1 up north, you will hit most of the major cities on the East coast. This is a good spot to take a quick snap of yourself by and then move along. There are many souviner shops around this area as well.
One thing you will definitely notice while walking around Key West is the dozens of free-range chickens. They have been protected inhabitats ever since cockfighting was outlawed in the 1970's.
Key West Cemetery
So a cemetery might be a weird place to check out while you are on vacation. However, this cemetery is a bit different. It has a very similar feel to New Orleans cemeteries, where all of the graves are above ground. While walking around the cemetery, you will find monuments to Cuban martyrs, victims of shipwrecks, and a Navy memorial. The cemetery's residents are stuffed in shoulder-to-shoulder and many tombstones are decorated displaying the personalities of the departed. You may also catch a few famous names as well.
Southernmost Point of the Continental USA
There is a large concrete painted buoy marking the southernmost point of the continental USA a short walk from the center of town. It is not actually the southernmost point, as that honor belongs to a private island 10 miles away. To be even more accurate, it is not even the southernmost point in Key West, as a bit of Fort Taylor Navy Base is a tad more south. It is still an extremely popular place to visit when in Key West.
On a busy day, there will likely be an hour-long line to get a photo in front of the painted buoy. I'd skip the line and get a photo of it in the few second break before the next tourists gets in front of it.
The Ernest Hemingway Home and Museum
Walking back up Whitehead Street, you will come across the Ernest Hemingway Home. It costs $14 for adults to enter and they only accept cash. They have guided tours or you can explore on your own. Ernest Hemingway has not been in the house since he died in 1961, but his cats' descendants still occupy the home. Take a look at the paws of the cats and you will notice most have 6-toes!
Across the street from the Ernest Hemingway Home is the Key West Lighthouse. You can walk up the steps and see the Keeper's quarters for $10. Once again, being frugal, we skipped the tour and admired it from the outside.
As it gets later in the day, it is a perfect time to hit up the famous Duval street. Duval street has neat hole-in-the-wall bars, art galleries, outdoor cafes, and restuarants. You will find bakeries selling their version of a Key Lime Pie and the original Sloppy Joe's bar. Key West has the most bartenders per capita and you will definitely believe it as you walk down the 1.3-mile street packed with bars. Key West is the perfect place for the ultimate bar crawl!
Near the end of Duval street, is Mallory square. It is where locals and tourists alike come to watch the sunset. Here in Key West, every sunset is a celebration. You will find jugglers, musicans, magicians, and all sorts of entertainers filling the square. This is a must-do and a perfect way to end your day in Key West.
Other Ways to Explore Key West:
Going on a group Key West Pub Crawl is an amazing way to explore Duval Street and make new friends. Having a local lead you around to the best bars to get the most popular drinks is so much better than just aimlessly trying to do it on your own. You get a bit of history, but a whole lot of the party. Or you can experience a bar crawl with a bit of a paranormal twist, by taking a Haunted Pub Crawl.
Key West is one of the most popular spots for parasailing and due to the high competition, prices are quite affordable. After we walked around Key West, we went out parasailing. It was an amazing, exhilarating experience seeing Key West and the ocean from above.
Want to be on one of the boats in the picture above enjoying some champagne while watching the sunset? You can sail out on a catamaran enjoying the views floating on the gorgeous turquoise water.
Don't want to or can't walk the whole way around Key West? You can take a hop-on hop-off trolley tour. You will be able to get to all of the sights in Key West with more time at each one.