A Historic Gem by the Sea in Key West
During our recent trip to Key West, my wife and I made sure to spend an evening at Mallory Square, and it quickly became one of the highlights of our trip. Standing at the edge of the Gulf of Mexico, Mallory Square has been part of Key West’s heart since the 1800s. Originally, it served as a bustling hub for the wrecking and salvaging industry, where goods from shipwrecks were brought in, auctioned, and sold.
Today, while the ships and sailors have mostly been replaced by artists and street performers, Mallory Square still holds onto that same adventurous spirit. Walking through the plaza, we could almost feel the layers of history beneath our feet, blending perfectly with the lively energy all around.
Why Tourists Flock to Mallory Square Every Night
Every evening as the sun begins to set, Mallory Square transforms into something magical. My wife and I had heard about the Sunset Celebration, but seeing it in person was something else entirely. Hundreds of people gathered together, all ready to toast the day’s end in the most joyful, Key West way imaginable.
It’s not just about the sunset—although most nights watching the sun melt into the horizon is breathtaking, our night was pretty cloudy—it’s about the atmosphere. Musicians playing island tunes, performers juggling
Waiting for the Sun to go down at Mallory Square
fire, the smell of fresh conch fritters in the air, and everyone, locals and tourists alike, sharing in the same carefree moment. It’s like one big, nightly festival that feels spontaneous yet timeless.
A Tapestry of Performers
The real soul of Mallory Square’s Sunset Celebration is the performers. Everywhere we turned, there was something incredible happening. We saw a magician pulling off unbelievable tricks, a tightrope walker performing daring feats high above the crowd, and musicians pouring their hearts into every song.
One of our favorite acts was a performer named Will Soto, who dazzled the crowd with his high-wire stunts. Another was Mustafa, a local legend whose soulful ballads filled the evening air. From sword swallowers to comedic clowns, it was an amazing showcase of human talent and creativity. You never knew what you might see next, which made wandering from act to act so exciting.
Every night, performers are out on the square
Where We Grabbed a Bite Nearby
After soaking in the performances, my wife and I worked up quite an appetite. Luckily, there are some fantastic places to eat just steps away from Mallory Square:
- El Meson de Pepe
A family-owned Cuban restaurant located right at Mallory Square. We enjoyed traditional dishes like Ropa Vieja and Cuban paella, all while sipping on mojitos and tapping our toes to live Latin music.
Address: 410 Wall St, Key West, FL 33040
Website: elmesondepepe.com - Two Friends Patio Restaurant
A cozy, open-air spot with live karaoke and a menu full of local seafood and steaks. We shared a delicious grilled mahi-mahi and had a blast listening to locals take the stage.
Address: 512 Front St, Key West, FL 33040
Website: twofriendspatio.com - Fisherman’s Café
For a quicker, more casual bite, Fisherman’s Café offered fantastic island-style sandwiches and conch chowder, perfect before or after the sunset.
Address: 205 Elizabeth St, Key West, FL 33040
Website: fishermanscafekeywest.com
From Street Vendors to Sit Down Table Service
Activities to Enjoy Around Mallory Square
After our amazing evening at Mallory, we discovered there’s so much more to do nearby:
- Dolphin Safari Charters
The next morning, we booked a Dolphin Safari adventure. It was a 3.5-hour boat trip where we got to watch wild dolphins play in the ocean and even snorkel over stunning coral reefs. Seeing dolphins in their natural habitat was unforgettable.
Website: Swim with Dolphins Key West area - Key West Aquarium
Just a short walk from Mallory Square, this charming historic aquarium gave us a close-up look at local marine life. We especially loved the touch tank and watching the shark feeding. - Key West Shipwreck Museum
History buffs like us couldn’t resist this museum. Full of shipwreck artifacts and entertaining reenactments, it gave us a whole new appreciation for the island’s adventurous past.
Sunset Sailing is another great activity
Our Lasting Memory of Mallory Square
Mallory Square isn’t just a place you visit—it’s a feeling you experience. My wife and I still talk about the night we spent there, laughing along with the street performers, holding hands as the sun dipped into the sea, and sharing in the pure magic that happens every single evening.
If you ever find yourself in Key West, you absolutely have to experience Mallory Square at sunset. It’s more than a tourist stop—it’s the heart and soul of the island.
Come for the sunset. Stay for the memories.
