I finally made it to one of the most iconic spots in the United States, Key West, Florida. Three days were filled with fun on the water, tasting around town, and of course, watching sunsets. If you’re planning your own trip to the southernmost point of the US, here’s my list of the best things to do in Key West!
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Drive Down the Keys
Unless you’re flying into Key West, there’s a good chance that the first thing on your list of things to do will be to take a Florida Keys road trip. I flew into Fort Lauderdale, met up with my bestie, Tamara, and we headed down the Keys.
It’s important to know that Google Maps will tell you that it should take just over three hours to reach Key West from Miami…but that’s not reality. Things are slow going and you’re going to want to stop and see sights along the way.
On our trip, we stayed at the Baker’s Cay Resort in Key Largo for two nights before continuing down to Key West so we could enjoy the journey more.
Read my friend Tamara’s post about our FL Keys roadtrip.
This is probably one of the most notable activities everyone must do in Key West. You have to go to Mallory Square at night about an hour or two before sunset and walk around the sunset celebration.
Performers will set up in an open area of Mallory Square and put on a free show. It might be music, magic, or even a show all about cat tricks! All performers are hoping to earn a thank you tip from those who chose to stop and watch.
This is not an organized event and you’ll notice there’s an interesting give and take with the artists where they each take turns to get everyone to gather around and watch.
You’ll want to arrive early and find a good spot early to watch the sunset along the edge of the water because it will build up and be three or four lines of people deep. Mallory Square is also right by the cruise terminal so if a cruise ship is in port things will be busier.
If you have multiple nights to enjoy Key West sunsets, consider going early to one of the bars that are set up along the water. The Sunset Pier looks like it has some of the best views of the sunset and we were bummed we discovered it on our final day of our trip.
Food tours are becoming one of my favorite ways to see a new city. You’re normally paired with a great guide who walks you around the city, letting you taste bites of food at 4-6 local restaurants.
Doing a tour like this makes a great lunch time activity on your day of arrival. You’ll get some good food along the way, but more importantly guided tours help you identify any places you want to go back to later. If you tasted something especially yummy, you can head back there for dinner or lunch the next day!
We did the Seafood Lover’s Tasting & Cultural Walking Tour with Rose from Key West Food Tours and he was fabulous. He had a great personality and shared so many fun stories about Key West and it’s citizens. I loved tasting tacos, lobster mac n’ cheese, conch ceviche, and some local brews on the tour.
I love a good sunset, and a sunset on the water is definitely my happy place. We headed out with Sebago tours on their Land’s End Sunset Sail. Our catamaran style boat had about 25 guests onboard, some stood along the railings; Tamara and I were lucky enough to snag a front bench spot.
While aboard we enjoyed some wine while the attendants brought around a four-course appetizer tasting for us to eat. We gently cruised around the water not too far from the coast of Key West while we listened to music, talked, and enjoyed the gorgeous Florida sun on our faces.
Eventually we made our way to the other side of Sunset Key, a luxurious island where some celebrities have homes. Sunset Key can block the sunset view from Mallory Square. But on the water we were given a full horizon view of the sun as she dropped below the water. The colors were gorgeous and it truly felt like a little bit of magic was in the air.
Eat Key Lime Pie
No trip to Key West would be complete without eating some key lime pie. It’s a huge thing down there and restaurants brag about having “the best”!
I took a different approach and tackled some other Key Lime foods besides pie. I had a key lime soda pop, key lime ice cream, and even a key lime martini! Take a walk around Key West and along the famous Duval Street and just watch how many key lime foods you’ll see advertised.
Tamara made it her mission to taste as much key lime pie as possible and compiled her picks for the best Key Lime Pie in the Keys.
Swimming and Snorkeling Tour
This was one of my favorite activities that we did! We headed out with Fury Water Sports on their Eco Tour. It was a bit cramped at first since we all had to ride along with a bunch of kayaks that were stacked in the center of the boat.
Our first stop was at a coral garden snorkeling spot. Some of the coral areas still show signs of damage from Hurricane Irma. A couple of snorkelers spotted a sea turtle while snorkeling.
We all got back onto the boat and headed to a new location where we anchored onto a sandbar to go exploring. We unloaded the kayaks and half of us headed out for a tour along the shore of a nearby island.
Our guide told us about all the wildlife living in those waters and we spotted a baby sting ray, baby nurse share, and she even picked up an upside down jellyfish.
After our kayak tour we headed back to the sand bar where we played and waded around in the water while enjoying a cold beverage. They had a couple of paddle boards available and I took one out for a little spin to see if I could spot any more wildlife.
Lunch was served on the boat while we were anchored. It was fried chicken and sandwiches with a few sides like fruit and veggies. It was surprisingly yummy! After lunch we watched a barracuda eat some chicken bones before heading back to Key West.
Our tour ended on a perfect note when we spotted a pod of dolphins that swam right by us.
Snap a Photo at the Southernmost Point of the Continental US
This is probably the most iconic symbol of Key West. This massive concrete buoy is painted declaring the point and there’s sure to be a line up. Try to go early if possible, otherwise find your favorite people and chat while you wait in the long line.
We only had three days in Key West, so here are the other top things to do that I didn’t get to experience but would have if I had more time!
Dry Tortugas National Park
Our National Park system is something to be celebrated and the Keys has their own National Park. Dry Tortugas National Park is about a 2 hour boat ride away from Key West and there are only certain operators that are allowed to transport guests to the islands.
My friend Bryanna visited Dry Tortugas and made this visit highlighting their visit:
And my friend Lesli has a great post sharing what there is to see and do at Dry Tortugas NP.
Visit the Ernest Hemingway Home
One of the most famous people that called Key West home was Ernest Hemingway. He lived and wrote in Key West for over 10 years and guests are able to tour his home.
Some of his most famous works were written while living in his home in Key West. ‘A Farewell to Arms’ was completed just shortly after moving to Key West with his wife, Pauline.
Another quirky thing about visiting the Hemingway House is that it’s home to around 40-50 polydactyl cats — cats with six-toes. The cats are the descendants of Ernest’s original six-toed cat, Snow White.
Climb Up the Key West Lighthouse
The Key West Lighthouse has a long history in Key West. It was demolished in a storm and later rebuilt again. You can pay for admission and learn about the history as well as getting the chance to climb the 88 steps to the top for a lookout over Key West to the ocean.
Bonus: Take a Photo at the Key West Postcard Mural
I snapped this photo of this great postcard mural while we were hurrying to another reservation. If you’re looking for a great memorable photo from the trip, or if you’re just doing it for the gram, grab a photo here.
BONUS: Head to the Beach
I say this with a bit of caution. The beaches of the Florida Keys aren’t the same as what you see on the beaches of the mainland of Florida. However, there are a couple of beaches in Key West.
I’ll also mention that there is a lot of sargassum along the beaches of the Keys recently and it often brings an unpleasant smell along with it. Many of the Keys beaches also have a lot of coral so you’ll want to have water shoes.
Smathers Beach on the south side of Key West near the airport. You’ll find palm trees and a good stretch of sandy beach to walk along. There’s another popular beach at the Fort Zachary Taylor State Park.
Hopefully, this post has given you plenty of ideas for things to do in Key West. I had so much fun during my girls’ trip to the Keys. It’s the perfect place for a laid back vacation! If you’re exploring more of Florida, check out these other scenic drives and areas in the state.