17 Best Fun Things to Do in Uptown, Key West

Uptown Key West is a lively neighborhood filled with exciting and unique activities for tourists. Located away from the hustle and bustle of downtown, this charming neighborhood offers a different side of Key West that many visitors often miss out on. From historic landmarks to fun outdoor adventures, there’s something for everyone in Uptown Key West. Let’s explore the top things to do in Uptown, Key West.

Key West Butterfly and Nature Conservatory

The Key West Butterfly and Nature Conservatory is a must-visit if you love nature and beautiful scenery. This unique indoor tropical garden is home to over 50 species of butterflies from around the world and vibrant exotic birds. Take a leisurely stroll through the enclosed garden and marvel at these creatures’ stunning colors and delicate movements. You can even learn more about their life cycle and habits through the informative displays throughout the conservatory.

Designer Octagon House of Key West

History buffs, this one’s for you! The Designer Octagon House of Key West is a stunning example of Victorian architecture and was once home to famous artist Robert Eugene Otto. Take a tour of this beautifully restored home and learn about this octagon-shaped gem’s unique design and history. You might even spot a ghost or two – the house is rumored to be haunted!


No trip to Key West is complete without some beach time! And Uptown has its lovely stretch of sand known as Beachside. This small and secluded beach offers crystal clear water and soft white sand, perfect for a day of swimming, sunbathing, or simply relaxing with a good book. Plus, there are several local eateries nearby where you can grab a bite or a refreshing drink.

The Hemingway Home and Museum

Literary enthusiasts will not want to miss the opportunity to visit the iconic home of one of America’s most beloved authors – Ernest Hemingway. This beautiful Spanish colonial-style house is where Hemingway lived and wrote some of his most famous works, including “A Farewell to Arms” and “For Whom the Bell Tolls.” Take a guided tour through the home and see how the writer lived, or simply wander around the lush gardens and visit with the famous six-toed cats that roam the property.

Mallory Square

Located on the western end of Key West, Mallory Square is a lively and bustling hub for tourists and locals alike. Every evening, visitors gather to watch the stunning sunset over the Gulf of Mexico while enjoying live music, street performers, and delicious food from local vendors. It’s a must-see for anyone looking to experience the vibrant culture of Key West.

Truman Little White House

History buffs, get ready for another unique and fascinating attraction – the Truman Little White House. Harry S. Truman once used this presidential retreat as a vacation home and has since hosted numerous other presidents and dignitaries. Take a guided tour through the house and learn about its rich history, including its role in the Cuban Missile Crisis.

Southernmost Point

Head to the southernmost point of the continental US for the perfect photo opportunity. A large buoy marks this iconic landmark and is a popular spot for tourists to snap a picture and marvel at how close they are to Cuba. It’s also a great place to enjoy the stunning ocean views and cool off with a refreshing sea breeze. 

Simonton Beach

No trip to Key West is complete without some time spent on the beach, and Simonton Beach is a hidden gem that shouldn’t be missed. Located just steps away from the hustle and bustle of Duval Street, this quiet and secluded beach offers a peaceful escape from the crowds. With crystal clear waters, soft sandy shores, and breathtaking views of the turquoise ocean, it’s the perfect spot to relax and soak up some sun.

Nancy Forrester’s Secret Garden

Nestled amidst the hustle and bustle of Uptown is Nancy Forrester’s Secret Garden, a hidden gem that will transport you to a tropical paradise. This lush oasis is home to over 80 rescued parrots, as well as a variety of other exotic plants and animals. Take a guided tour or simply wander around the garden on your own, and don’t forget to stop by the gift shop for some unique souvenirs.

City Zoo Gallery

For art lovers, a visit to the City Zoo Gallery is a must. This funky and eclectic art space features the work of local artists and showcases a wide range of styles and mediums. From paintings and sculptures to jewelry and home decor, there’s something for everyone to admire and take home as a one-of-a-kind souvenir from Key West.

Dry Tortugas National Park

Located just 70 miles west of Key West lies the stunning Dry Tortugas National Park. This remote and unspoiled island is accessible only by boat or seaplane, making it a true hidden gem. Spend the day exploring the pristine beaches, snorkeling in the crystal-clear waters, and marveling at the historic Fort Jefferson. Dry Tortugas National Park is a nature lover’s paradise with abundant marine life and breathtaking views.

Duval Street

While it may be one of the more well-known attractions in Key West, no trip to Uptown is complete without a stroll down Duval Street. This bustling street is lined with colorful shops, lively bars and restaurants, and various street performers. It’s the perfect place for people to watch, grab a drink or a bite to eat, and soak up the vibrant atmosphere of Key West.

Key West Lighthouse

For a unique perspective of Uptown, make your way to the top of the historic Key West Lighthouse. Built in 1847, this lighthouse offers stunning views of the surrounding area and is a great spot to snap some Instagram-worthy photos. Don’t forget to stop by the Keeper’s Quarters Museum to learn about the fascinating history of the lighthouse and its keepers.

Southernmost Point

You can’t visit Key West without photographing the iconic Southernmost Point buoy. Located at the southernmost tip of the continental United States, this colorful buoy marks just 90 miles to Cuba. It’s a popular spot for tourists, so be prepared to wait in line for your turn to snap a photo.

Sunset Key

Just a short ferry ride from Uptown lies Sunset Key, a private island resort that offers breathtaking views of the famous Key West sunset. Spend an evening sipping cocktails and watching the sun dip below the horizon at one of their waterfront restaurants, or simply relax on the beach and take in the spectacular view.

Tennessee Williams Theatre

For theater buffs, a visit to the Tennessee Williams Theatre is a must. This historic venue has been hosting performances since 1912 and is named after the famous playwright who called Key West home for many years. Catch one of their shows or events and experience the rich cultural history of Key West in a truly unique setting.

South Beach

Last but certainly not least, we have South Beach – a beautiful and secluded spot with crystal clear water and soft white sand. This beach is perfect for swimming, sunbathing, or simply taking in the stunning views of the Atlantic Ocean. Plus, it’s located near many local restaurants and shops, making it a convenient stop for visitors exploring Uptown Key West.

Uptown has so much to offer and is not to be missed on your next trip to Key West. Whether you are looking for a peaceful escape or an exciting night out, this vibrant neighborhood has something for everyone.

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