14 Things You Won’t Want To Miss in Key West, Florida

Key West, Florida is one of the most desired vacation spots in the country. Known for its laid-back charms and spectacular water adventures, Key West is a sensational place to get to know. From the iconic drive getting here  to cocktails at sunset and delicious key lime pie, here are 14 things you won’t want to miss in Key West to enrich your trip just a little more. 

#1 Sightseeing with Old-Town Trolley

See the best of Key West on the 13 stops aboard Old-Town Trolly Tours showcasing over 100 points of interest. With stops including the rum factory, Hemingway House, Little White House, and Mallory Square, it is a wonderful way to see the area. They also help with saving money and time looking for a parking place. Old Town Trolley runs every 30 minutes (from each stop) from 9 AM to 4:30 PM.

Get the most out of your tour by riding the entire loop (90 minutes) before deciding which stops you want to take. Children 12 and under ride for free. Buy your tickets online for bonus savings. 

#2 Sipping Cocktails at First Flight

Enjoy outdoor seating and stellar cocktails at First Flight Island Restaurant and Brewery, a friendly aviation-themed eatery serving American style dishes. Fittingly named, the first Pan-Am flight tickets were sold at this location in 1927. Beer lovers might fancy a Southern Clipper Wheat or Havana Red Ale at this Southernmost Microbrewery. I recommend the First Flight Mules, available in blueberry, orange, basil, or  strawberry.

#3 Eating a Tasty Key Lime Treat 

Indulge in a world-famous chocolate-dipped Key Lime Pie on a Stick or one of the other classic favorites at everybody’s preferred key lime shoppe in the Keys, Kermit’s Key West Key Lime Shoppe. You may even catch Kermit outside of the store as he waves to the passersby encouraging them to stop for a look. Kermit’s creations range from cheesecake to salsas, and cookies to cocktail sauce. My favorite? The Strawberry Key Lime pie. 

#4 Taking Nature Photos

Take a selfie or group photo in front of the enormous, sacred Kapok tree in the heart of Key West. If you are not familiar with these exquisite trees, Mayans believed that souls of their dead climbed a (mythical) kapok tree’s branches to reach into heaven. Key West also has beautiful banyan trees— another perfect photo opportunity. 

#5 Staying in a Luxury Hotel

I can’t think of a better place to call home during your Key West trip than Oceans Edge Key West Resort Hotel & Marina. This luxury hotel (with all rooms facing the ocean) offers plush accommodations, free Wifi, and six outdoor pools. The setting is fantastic, with an heir of privacy, excellent customer service, and stellar amenities being their top goal.

Though located on Stock Island, Key West’s friendly neighbor, you are afforded beautiful views of the harbor and have much less traffic. A hotel shuttle will take you to the popular Key West attractions and you won’t have to fight for a parking space. These luxury digs are most impressive and destined to be your favorite hotel in the Florida Keys. 

#6 Exploring Fort Jefferson

Located 70 miles from Key West, either via boat ride or seaplane, explore the history of Fort Jefferson, a magnificent National State Park and unfinished coastal fortress. The fort and national park are located on the Dry Tortugas Island, a remote area with water every bit as beautiful as the Caribbean islands.

Fort Jefferson spreads over 16 acres on the island and contains 16 million bricks, all of which had to be transported and hand carried to this remote location. Bring your bathing suit and enjoy swimming or snorkeling at the world’s third largest reef while you are there. The array of fish you can see is second to none!

Learn more about discovering the Dry Tortugas in this post.  

#7 Experiencing Mallory Square Sunsets

Visitors and locals alike pile into Mallory Square for possibly the best sunsets they’ve ever seen. There is nothing like a Key West sunset. While it may sound redundant, people come out daily at sundown to experience the magnificent showing night after night. Along with the sunset show are food vendors, street performers, music, and other entertainment making this a most lively part of town.

This is also where you will find some of Key West’s best shopping, including Shell Warehouse and Caribbean Congo. Come early, as the square gets very busy when it gets to be that magical time of evening. 

#8 Touring a Famous House

Hemingway is one of America’s most prolific writers and Nobel Prize winners. He penned some of his greatest novels and short stories from his modest estate home in the Florida Keys, including A Farewell to Arms. The historic Spanish-Colonial home became a US National Landmark in 1968 and continues to draw thousands of visitors each year who want to see where the magic took place.

While at the Ernest Hemingway Home and Museum, be on the lookout for Hemingway’s six-toed cats, still wandering around the property. You can also see the Key West Lighthouse across the street. 

#9 Going Clubbing

It wouldn’t be a trip to the Florida Keys without letting your hair down and getting funky at one of the countless bars, clubs, drag shows, or discos in Key West. It’s always  5 o’clock somewhere in the Keys. From traditional bars to risqué clubs, there is plenty of fun for everyone in this special location.

Mary Ellen’s Bar and Restaurant is a dive bar with a cool vibe, tasty menu (gourmet grilled cheeses, y’all!), and nightly events/entertainment. 801 Bourbon Bar and Bourbon Street Pub (both LGBT) were perfect for people watching, live entertainment, great music, and a vibrant atmosphere. Bull and Whistle and Green Parrot Bars are other popular choices. 

#10 Browsing Incredible Art 

Browse unique fine-art pieces by well-known artist Robert Wyland and other contemporary names in this beautiful gallery. The Key West location of Wyland Galleries is actually the flagship of the brand and 40-year location of the talented marine-life artist. Wyland’s pieces include Disney-themed paintings to bronzes, and lucites to paintings. 

#11 Checking Off the Southernmost Point

A bucket list item of yours might be seeing or having your photo made at the Southernmost Point landmark (in the continental US), a popular spot for tourists to capture the memory of Key West. You can also see the tip of Cuba from this point. Be prepared to wait in a line, but the big red-striped concrete buoy photo is a must in Key West. Around three million people visit the Southernmost Point each year. 

Consider visiting the Key West Shipwreck Treasure Museum across the street for a look at the 1800s version of the town. 

#12 Visiting the Harry S. Truman Little White House

Take a guided tour of the only Florida Presidential Museum, on the National Register of Historic Places. The Little White House was built for a military commandant (officer in charge) and paymaster in 1890, but the dual residence was converted into a single family dwelling that attracted US presidents. Clinton spent the weekend there, FDR came three times, JFK prepared for a summit prior to the Bay of Pigs Invasion, and Eisenhower recovered at the house after a heart attack. It is also where the Department of Defense was created. 

Nobody loved or spent more time at the Little White House than Harry Truman, of which the name was changed to in later years. Truman spent 11 working vacations at the charming house where he and wife Bess loved having friends and dignitaries over for card games and entertaining. 

#13 Enjoying the Beaches of Key West

Explore one of the six beaches of Key West while you work on your tan, read a good book, or relax. The nearby beaches are Higgs, Smathers, South, Dog, Simonton Street Beaches, and Ft. Zachary Taylor Historic National Park. 

Photo by Rob O’Neal.

#14 Celebrating Mile Marker Zero

The Mile Marker Zero sign is one of the most popular Key West attractions. Getting your picture taken in front of the sign it is half the fun of arriving at it. The US1 Mile Marker Zero sign is an Instagram-Worthy stop, but like the Southernmost Point, serves as proof of your being in Key West. The 2,369 mile interstate runs from upstate Maine to Key West. 

Eat Delicious Key West Cuisine, Too

Key West is a place for foodies to sink their teeth into amazing cuisine and the freshest seafood around. From peel & eat shrimp to mussels and lobster, you are going to love the local eateries. Not a seafood fan? No worries. We had plenty of other decadent dishes, too, including gourmet tacos, impressive steaks, burrata salads, and buffalo wings. Your options are unlimited, but do save room for a key lime dessert. Check out our guide to the best restaurants in Key West. 

Key West: An American Favorite Vacation Destination 

Besides these 14 things, there are countless other ways to spend time in Key West, Florida. This coveted Southernmost destination remains sacred for sipping cocktails, watching sunsets, and enjoying a low-key vacation with plenty of fun for the entire family.

With great historical attractions, scenic beaches, and photo-worthy spots, Key West has it all. What is your favorite thing to do in Key West? 

More Things You Won’t Want to Miss in Key West

Thanks to the Florida Keys for hosting our adventures. As always, opinions and reviews are 100% mine and unbiased. Thank you for reading.

You can learn more about the Key West and the Florida Keys by visiting their tourism site. 

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