Making the Most of Margaritaville at Key West’s Sunset Celebration

The Key West Sunset Celebration is an island must-do. (Photo: Quentin Bargate / Alamy)

Visit Key West, Florida and you’re likely to hear some say, “see you at sunset!” As dusk sets in, the island’s Mallory Square pays homage to sunset with a nightly party to rivals any major holiday. Every evening, a rotating cast of street performers, art vendors, food sellers, and, of course, locals and tourists, gather in Mallory Square two hours before sunset to kick off the Sunset Celebration.

Before planning your trip, check out which activities and performances will happen at Mallory Square’s Sunset Celebration each night. Our Mallory Square guide helps you navigate the entertainment so you get the most out of your visit.

Street Performers

Will Soto – For over 20 years, Will Soto has been entertaining crowds at the nightly Sunset Celebration festivals. Though he’s over 60 years old, Will still walks a tightrope three evenings a week, juggles, and dances with fire for the crowds in Mallory Square. Originally from New Orleans, Will has a background in gymnastics. When visiting the island in the 1990s, he became enamored with the eclectic nature of Mallory Square and is now one of its most integral performers.

The Jeep and Cleo Show – Who doesn’t love a pup? Always a crowd favorite at the Sunset Celebration, Mr. Jeep and his dog Cleo perform different acts such as tightrope walking (yes, Cleo can do it), making balloon animals, conducting magic shows, and of course, animal tricks.

The Rick & Jan Variety Show – You’ll get the giggles at this fast-paced comedy show experience. Rick and Jan’s lively show includes of a comedy routine, juggling, unicycling, and music performances.

Musical Performances

Musical artists present at the nightly Sunset Celebrations vary, but some of the crowd favorites include Mustafa, Bert Lee, and Dave Vizard. Each presents the music unique to the island vibe of Key West.

Artisan Goods

Each Sunset Celebration features variety of artisan goods made by local vendors. Give yourself time to explore the artists’ tables and bring back a memento for yourself or your friends and family back home. Popular jewelry vendors include Island Designs by Barb Winko and Anita Whitney Designs. If you’re looking to bring the island vibes back home, pick up a local, hand-designed t-shirt, hat, or clothing accessory from Michel Delgado Design or Hand Painted T-Shirts. Looking for art? Whether you’re interested in oil paintings or pastel portraits, artists like Laura Black Art and Art by Janis create an array of works.

After Sunset

Once the sun dips below the horizon, you’ll need to eat. Get your grub on at one of these local favorites.

El Meson de Pepe – Opened in 1984, El Meson de Pepe is a family-owned and operated Cuban restaurant serving traditional Cuban cuisine with a Key West flare. Try ropa vieja, a traditional meal consisting of shredded beef stewed with vegetables in red wine. Enjoy your dish alongside rice, black beans, and sweet plantains.

Duetto – For a sweet treat while exploring Mallory Square, check out Duetto and taste one of the restaurant’s delicious flavors of Italian gelato. Twelve varieties are made fresh daily using milk and natural, local ingredients. If you’re craving something more filling, try one of Duetto’s pizzas, like the “Lombarda” that’s topped with gorgonzola, caramelized onions, walnuts, mozzarella cheese and fresh arugula.

Smokin’ Tuna Saloon – Serving up fresh fish, sandwiches, and traditional Key Lime pie, Smokin’ Tuna Saloon is a hot spot for Key West cuisine as well as live music. The restaurant regularly hosts the Key West Songwriters’ Festival events. Check their website before visiting to see what live music will be playing during your trip to Mallory Square in Key West.

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