Must-Do Guide to Key West According to Locals

• The Hemingway Home and Museum: Ernest Hemingway lived in Key West from 1931 to 1939 and wrote some of his most famous works here. His home is now a museum that offers tours of the property, including his writing studio and the famous swimming pool. The grounds are beautiful and you have to see the famous six-toed cats for yourself!

• Key West Lighthouse: I might be a little biased because I got married on the grounds of the Key West Lighthouse but in my opinion, it’s definitely worth the trip! If you’re looking for a little aerobics, climb the 88 steps to the top and take in the best aerial views of Key West.

• Skydiving: This thrill-seeking activity is not for everyone, but if you are an adrenaline junkie like me, you're not going to want to miss skydiving over the Florida Keys. It has been named one of the top 10 skydiving destinations in the world and I can confirm the views are incredible. When I jumped we could see nursery sharks in the water and we even flew through a rainbow!

• Rum Runner Boat Sandbar Trip: If you’re in Key West you have to make sure to get out on the water. One of my favorite ways is by renting a Rum Runner boat to take you out to one of the nearby sandbars for an afternoon of relaxation. Most of these depart from the east side of the island but if you rather depart closer to Duval, I recommend renting through Lagerheads Beach Bar & Watersports. It’s BYOB so make sure to bring whatever drinks you want to fill up the onboard cooler with.

• Sunset Sail: Another classic way to get out onto the water is by going on a sunset sail. Multiple companies will take you out and serve cocktails while you take in the views. Some even include live music onboard. My recommendation is Sebago Watersports. They have a variety of boats with different price points depending on what you’re looking for.

• Conch Train Tour: One of my favorite things about Key West is its walkability. But when your legs are tired, I recommend hopping on the Conch Train. It’s a fun and informative way to explore the island’s charm and history aboard a quirky, open-air train. Is it touristy? Yes. A little cheesy? Also, yes. But it’s the perfect way to see the island, especially on a hot day if there isn't much of a sea breeze.

• Kayak through Mangroves: Another unique Florida Keys experience is kayaking through the Mangroves. This adventure is perfect for nature lovers, kayakers of all experience levels, and anyone seeking a unique perspective of the island’s ecosystem. Lazy Dog Adventures offers well-priced tours and who knows, you might even see a manatee!

• Head to the Beach: Key West isn’t necessarily known for its beaches… but when you come to a tropical destination with turquoise waters, it’s hard to resist wanting to dip your toes in. You have three main options: Smathers Beach, Higgs Beach, and Fort Zachary Taylor Park. I’d recommend Fort Zachary Taylor Park. They have lounge chairs with umbrellas to rent and a snack bar for when you get hungry. Make sure to bring some water shoes though. The sand is made up of small pieces of coral and can be pretty rough on your feet.

Day Trips:

Day Trip to Dry Tortugas

If you’ve made it all the way to the Southernmost Point of the Continental U.S.A., you’ve got to go a little farther and take a day trip to the Dry Tortugas. This unique National Park is 70 miles west of Key West in the middle of the Gulf of Mexico. There are two options to get there: The Yankee Freedom High Speed Ferry or a chartered seaplane.

Upon arrival, you'll be greeted by the majestic Fort Jefferson, a massive 19th-century military fortress. This fascinating structure is the largest brick fort in the Americas and offers a glimpse into the island's rich history. Make sure to head to the top to snap some incredible pictures.

After a quick tour of the fort, head down to the beach for some incredible snorkeling along the walls of the fortress. The coral reefs are so colorful and you'll see so many different fish! There isn’t much shade on the island so make sure to keep lathering on that reef-safe sunscreen.

After several hours exploring the island, you’ll head back to Key West. If you’re taking the ferry, make sure to grab a piña colada to sip on as you enjoy the ride. Tickets are booked up sometimes months in advance so if you’re interested, let your travel advisor know ASAP so they can snag tickets for you. You don't want to miss out on this once-in-a-lifetime experience!

• Mo's Restaurant: Mo’s is the epitome of a hidden gem. If you’re looking for a fancy establishment, don’t come here. If you’re looking for some of the best Caribbean/Haitian food you’ve ever had in your life, this is your place. The snapper here is incredible and don’t skip the oxtail! The portions are huge so can easily split an entrée. However, we never do because you better believe I’m taking the leftovers with me.

• Doing Work Coffee Shop & Roaster: There are tons of great coffee options in Key West, so many that they all start to blend together in my mind. This one, however, stands out. They source their beans from all over the world and roast them in-house, ensuring the freshest and most flavorful coffee possible. You won’t find this shop unless you’re looking for it. I walked past it many times and never noticed it until a local told us we had to check it out!

• Pepper Pot Island Café: This cafe specializes in Trinidadian cuisine and is the perfect spot to grab a bite before heading to Fort Zachary Taylor Beach. Expect flavorful dishes like curried goat, stewed chicken, and roti, a flatbread filled with savory fillings. Everything on the menu is excellent so you really can’t make a wrong choice here!

• Lagerheads Beach Bar & Watersports: I am a big-time beach lover, which sadly, Key West does not have a lot of. However, tucked away at the end of Simonton Street is a small beach bar where you can relax, enjoy the soft sand, and grab a bite to eat. The drinks here are cheap so you can have plenty. Their dock is also where the Rum Runner boat departs from.

• Sunset Pier: This is probably the most touristy of all my recommendations. However, it is undeniably the best spot to watch the sunset from land. Tons of people will flock to Mallory Square but if you go just north, there is a long dock lined with colorful bar stools giving everyone a great vantage point to watch the sun go down. Come here early and snag a spot because it does fill up.

• Red Shoe Island Bistro: This bistro offers a charming escape from the typical Key West scene. They’re only open for dinner six days a week so be sure to grab a reservation in advance. Expect a touch of French sophistication with a focus on fresh seafood. Everything we ate was incredible, but I will return time and time again to have what is, in my opinion, the best key lime pie ever.

• General Horseplay: If you’ve had your fill of sweet, fruity drinks, head over to General Horseplay for some creative craft cocktails. It does get pretty crazy here on the weekends so I would recommend coming here on a weeknight. Hang out inside in the dimly lit bar with vintage décor, or head out back for some fun live music. The mocha espresso martini is a must!

• The Rum Bar: This bar boasts a massive selection of over 350 rums from all over the world! Whether you're a rum aficionado or just curious to explore, the bartenders here are very knowledgeable and will help you find the perfect sip. The inside is small and probably only seats 15 people. Perfect place to end the day with a nightcap and strike up a conversation with the locals.