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A visit to Key West, Florida is a trip like no other. A vibrant island located at the southern tip of the Florida Keys, Key West is the land of tropical sunshine, amazing water activities, and a lively downtown known for its haunting history and world-famous sunsets. It’s the ideal spot for a weekend jaunt – as relaxing or invigorating as you want it to be. Here’s an itinerary for a weekend in Key West to help get your adventure started!
Though Key West is only four miles long, it is jam-packed with enough gems to easily fill a week. But if you only have three days, here’s an easy Key West weekend itinerary that works for families as well as adults-only trips. Plus, there are many free things to do in Key West.
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Weekend in Key West Itinerary – Getting Around
There are so many incredible things to explore on Key West, Florida – both indoors and out. My family had an amazing time on our recent visit.
We got around via the trolley, which serves as public transportation to many Key West attractions. Both the Conch Tour Train and Old Town Trolley companies have multiple stations and ticket windows and offer narrated tours of the town with hop on/hop off privileges. It made getting around easy.
If you don’t hop off, the trolley ride takes about an hour and a half to make the full loop. But I recommend using the trolley as both a tour and a mode of transportation throughout your stay, saving time and making it easy to get from place to place.
Day One: Learn About Key West’s Historic Past
Hemingway House and Museum – 907 Whitehead Street
Not going to lie – I wanted to visit this iconic place just as much to see the famous six-toed cats as to see where Ernest Hemingway lived and worked during his years on Key West.
Nestled in the heart of Old Town Key West, this unique property was home for more than 10 years to one of America’s most honored and respected authors. It’s where Hemingway worked on many of his literary masterpieces. It is now a museum dedicated to the writer. Beautiful gardens surround the house.
The Ernest Hemingway Home is also home to approximately 40-50 polydactyl (six-toed) cats. (You don’t need to pay to go inside to see them—they’re everywhere!) A ship’s captain gave Ernest Hemingway a white six-toed cat. Some of the cats lounging around the museum grounds are descendants of that original cat, named Snow White. The cats are well cared for and obviously used to visitors, so don’t hesitate to reach down and give the kitties some love if they look willing.
Key West Lighthouse
After you visit the Hemingway House, walk to the nearby Key West Lighthouse. Built in 1848 by the U.S. Navy, the Key West Lighthouse today serves as a museum dedicated to the lighthouse keepers who lived and worked there over the years. Climb the 88 steps to the top for a fantastic view of the city, and go into the adjoining Keeper’s Quarters to view photographs and belongings of the former lighthouse keepers.
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Discover Haunted Key West
After dinner and perhaps a few drinks at Sloppy Joe’s on Duval Street, cap off Day One by exploring the darker side of Key West with a nighttime ghost tour. My 13-year-old son and I went on the Ghosts & Gravestones Tour, which is a combo trolley and walking tour. The trolley took us past the city’s most notoriously haunted sites, and then into two buildings – the East Martello Fort and the Shipwreck Treasure Museum – to experience some haunts first hand. Tours are led by “Ghost Hosts.”
The Ghosts & Gravestones Tour was cool and just moderately scary enough for my 13-year old. For older teens and the truly daring, make sure you borrow an electromagnetic meter from the tour guide to detect the presence of ghosts.
Day Two: In, On and Near the Water
With its tropical warm waters and some of the most amazing coral reefs in Florida, Key West is prime for snorkeling, jet skiing, parasailing, and other ocean adventures.
There are several tour companies that offer fishing and watersport excursions in Key West. We did a combo sailing and snorkeling tour with Sebago Watersports. If you prefer more action, choose the Power Adventure excursion, with snorkeling, jet skiing, parasailing, kayaking, and paddle boarding. All tours provide food and drinks, and the staff is attentive and friendly.
If you are more of a landlubber, spend Day 2 at Dry Tortugas National Park, home to the magnificent 19th Century Fort Jefferson. Located about 70 miles from Key West, the cluster of seven small islands is only accessible by boat or seaplane. The park is home to a wide range of tropical birds, marine life, coral reefs. Fort Jefferson is surrounded by a moat and was used as a prison during the Civil War. Take the guided tour to get the full experience.
Whichever excursion you choose to start your day, plan to get to Mallory Square before nightfall. Facing the Gulf of Mexico, the waterfront plaza is a hub in Key West’s historic Old Town and world famous for its sunsets. This nightly “Sunset Celebration” is one of the most popular things to see and do in Key West. This tradition began in the 1960s, and the celebration still takes place every day.
TravelingMom Tip: Get there early! Every evening before the sun begins to set, hundreds of tourists gather at Mallory Square. That draws artisans selling their wares and live music and street performers. The area fills up fast!
Day Three: Butterflies and Beaches
Start your final day in Key West at the Key West Butterfly and Nature Conservatory. More than 60 species of butterflies and 20 exotic birds fly freely throughout the glass-enclosed, tropical habitat. It’s also home to a wide spectrum of bright and beautiful flowers, plants and bushes for the butterflies to land on, putting visitors quite literally in the center of all the action.
Just down the street from the Conservatory is the Southernmost Point, arguably Key West’s most famous landmark. A massive, colorful concrete buoy marks the Southernmost Point of the USA. It is closer to Cuba (90 miles) than it is to mainland Florida.
The Most Photographed Spot in Key West
Southernmost Point is one of the most photographed spots in all of Key West. As such, it also tends to get crowded as people line up to wait their turn to get a photo. It is not unusual to see upwards of 100 people in line. On our visit we got lucky (if you can call it luck) to hop off the trolley at the site just as a torrential rainfall started. Armed in our rain ponchos, we were the only ones crazy enough to be at the shore. So while we didn’t have to wait in line to get a picture, we did get more than a little wet! Rain or shine, don’t miss your chance to get a photo at the Southern Most Point in the United States.
Since you are already at the waterfront, end your visit to Key West with some beach time and perhaps a fruity cocktail at the Southernmost Beach Café, located right on the sand by the Southernmost Point.
Where to Stay for a Weekend in Key West
We made the Best Western Hibiscus Motel our home base and I highly recommend it. This lovely hotel is centrally located (I realize that’s a cliché … but it really IS centrally located), just a short walk to the beach in one direction and a short walk to the island’s main attractions, restaurants and shops in the other. The 61 guestrooms are surprisingly spacious, with two queen beds, a refrigerator, coffee maker, complimentary Wi-Fi and a bountiful free breakfast. There is a lovely courtyard with heated pool and Jacuzzi, which we enjoyed every night.
The Best Western Hibiscus Motel also is an easy walk to downtown and an even easier walk to the nearest trolley stop.