15 Ways to Experience Arts in Key West
Long a haven for writers, artists, and dreamers, Key West continues to inspire with its sun-soaked streets, storied past, and vibrant creative spirit.
With its breezy “come as you are” mantra, the Florida Keys has long been a haven for artists. Ernest Hemingway lived in Key West throughout much of the 1930s where he famously spent his mornings writing, his afternoons fishing on the Gulf Stream aboard his beloved boat Pilar and his evenings drinking at his friend Joe Russell’s bar Sloppy Joe’s. His lifestyle epitomizes the many pleasures that Key West offers visitors today. Throughout the 20th century, the island continued to be a home for writers and artists, from playwright Tennessee Williams to poet Elizabeth Bishop and author Judy Blume today. In the 1970s, Jimmy Buffett began writing and recording music in Key West, eventually introducing the “parrothead” lifestyle to the masses with hit songs, from Margaritaville to It’s 5 O’clock Somewhere.
The picturesque archipelago has also captured the imagination of Hollywood, serving as filming locations for several movies and TV shows, from Humphrey Bogart’s Key Largo in 1948 to the hit TV series Bloodline set in Islamorada, Arnold Schwarzenegger’s 1990s thriller True Lies whirring in a helicopter above the Seven Mile Bridge and James Bond’s License to Kill in Key West. Today, the Florida Keys local arts scene provides a distinctive perspective into life in paradise. And there are so many fantastic ways to soak it all in, from art galleries to museums, historic sights and the performing arts.
The Key West Museum of Art & History at the Custom House spans two floors of exhibition space.
Key West Museum of Art & History at the Custom House
Situated in a striking red brick building on Mallory Square, which originally served as the island’s custom house, post office and federal courthouse, the Key West Museum of Art & History at the Custom House spans two floors of exhibition space. It’s home to a fantastic collection of folk artists Mario Sanchez’s painted relief woodcarving depicting scenes of island life from the 1930s on. A collection of Tennessee Williams’s haunting, surrealist paintings from the 1970s are also on display, offering another perspective on the legendary playwright’s creative practice. Other exhibits detail the history of Henry Flagler’s Oversea Railway and WPA artists in Key West during the Great Depression. On the grounds surrounding the Custom House, you’ll find life size bronze sculptures by Seward Johnson depicting people who look like they’ve simply frozen in place wandering around Key West with you.
Hemingway’s only novel set in the United States, To Have and Have Not, is set in Key West—it’s the perfect souvenir to pick up in the museum’s gift shop.
Hemingway Home & Museum
Arguably Key West’s most famous literary lion, Ernest Hemingway lived on the island throughout the 1930s with his second wife Pauline Pfeiffer in a home on Whitehead Street that’s now a museum. His time in Key West was his most prolific writing period and he wrote much of For Whom the Bell Tolls, To Have and Have Not and The Green Hills of Africa in his writing studio on the property, which he accessed across a catwalk from his second-floor bedroom. When you visit, opt for a guided tour for entertaining stories about Hemingway’s time in Key West. You’ll also commune with descendants of his original six-toed cat Snow White who roam the grounds freely. Fun Fact: Hemingway’s only novel set in the United States, To Have and Have Not, is set in Key West—it’s the perfect souvenir to pick up in the museum’s gift shop.
A community hub for arts and culture in Key West on the corner of Eaton Street, The Studios of Key West is home to working artist studios and an art gallery.
The Studios of Key West
A community hub for arts and culture in Key West on the corner of Eaton Street, The Studios of Key West is home to working artist studios and an art gallery. It regularly hosts special events and classes in all disciplines, from visual arts to literature, the performing arts and beyond. Swing by the gallery to view the latest exhibition, featuring new works by local artists or artists in residence. These shows often premier during First Thursday Open Houses when artist studios are also open to visitors. Every Tuesday evening, the Hugh’s Views rooftop hosts a community happy hour often with live entertainment timed perfectly to the sunset. Check out The Studios of Key West’s events calendar ahead of your visit for special concerts, workshops, talks and classes.
A cornerstone of The Studios of Key West complex, Books & Books is a branch of Miami’s indie bookstore empire.
Books & Books
A cornerstone of The Studios of Key West complex, Books & Books is a branch of Miami’s indie bookstore empire. In Key West, the shop is owned and operated by legendary author and Key West resident Judy Blume. Author of Are You There God? It’s Me Margaret, Blume is often found in the shop shelving books to the delight of unsuspecting customers who grew up reading her books. Home to a diverse range of new arrivals and classics, you’ll also find books by local authors and on topics central to Key West. With its relationship to The Studios, Books & Books also sells art supplies. The shop regularly hosts talks by high profile visiting authors, providing a wonderful literary community for readers and writers in Key West.
Nance Frank’s Gallery on Greene represents dozens of Key West, including folk artist Mario Sanchez, Peter Vey’s Impressionistic island scenes, photographer Michael Marrero and the mixed media works of Suzie de Poo.
Gallery on Greene
Key West is home to a local gallery scene with a range of curatorial perspectives. Nance Frank’s Gallery on Greene represents dozens of Key West, including folk artist Mario Sanchez, Peter Vey’s Impressionistic island scenes, photographer Michael Marrero and the mixed media works of Suzie de Poo. With a longtime relationship with Cuban artists, Frank also leads group and private tours of galleries and artist studios in Havana. Beyond Gallery on Greene, embark on a self-guided Key West gallery crawl by simply hopping on a bike and setting out towards Duval Street. Here, amongst other galleries, you’ll find Archeo, which specializes in authentic Gabbeh rugs, African art and fine jewelry. On White Street, Harrison Gallery and Stone Soup Gallery both showcase works by local artists.
Set beyond a kitschy neon-lit Art Deco façade on Eaton Street, the Tropic Cinema is Key West’s non-profit indie art house cinema supported by donations and a volunteer staff.
Tropic Cinema
Set beyond a kitschy neon-lit Art Deco façade on Eaton Street, the Tropic Cinema is Key West’s non-profit indie art house cinema supported by donations and a volunteer staff. Home to three intimate theaters, it screens critically acclaimed new releases, foreign films, indie films and classics. The concession stand offers classic movie-going snacks, like popcorn, candy and soda, alongside wine, beer, cheese and crackers. There’s perhaps no better way to while away a hot, sunny afternoon in Key West than in the cool, dark air conditioning of a Tropic Cinema theater, getting lost in a great film.
Set inside what was once an 1840s era Baptist church on Eaton Street, the Key West Theater is a dynamic performing arts venue playing host to a fantastic lineup of musical acts, as well as comedy and variety shows.
Key West Theater
Set inside what was once an 1840s era Baptist church on Eaton Street, the Key West Theater is a dynamic performing arts venue playing host to a fantastic lineup of musical acts, as well as comedy and variety shows. Home to both a 278-seat main stage theater and a more intimate Back Stage Listening Room, the venue has attracted everyone from Jimmie Vaughan to Donavon Frankenreiter, Alan Cumming and Blues Traveler. Local acts, from singer-songwriters to comedians and cabaret shows also step into the spotlight here. And Margaritaville legend Jimmy Buffett performed some of his final shows at the venue in a set of surprise concerts in 2023.
At the Tennessee Williams Museum on Truman Street, learn more about the playwright’s career and time in Key West through photographs, memorabilia and newspaper clippings.
Tennessee Williams Museum
The great 20th century playwright Tennessee Williams bought a home in Key West in 1950 at 1431 Duncan Street where he resided on and off for the rest of his live over the next three decades. Williams famously enjoyed spending his mornings swimming at the beach at the end of Duval Street before writing every day. Today, his home is privately owned, but you could still take a bike ride past and let your imagination wander. At the Tennessee Williams Museum on Truman Street, learn more about the playwright’s career and time in Key West through photographs, memorabilia and newspaper clippings. There’s also a typewriter he used while living in Key West and a scale model of his home on Duncan Street.
Emily Bishop wrote much of her debut collection North & South while living in Key West.
Elizabeth Bishop House
Celebrated poet Elizabeth Bishop arrived in Key West at the age of 25 and eventually bought a home at 624 White Street in 1938. She was drawn to Key West for its natural beauty and wrote much of her debut collection North & South while living on the island. The Key West Literary Seminar, which hosts an annual conference on the island every January, recently acquired her home with the intent to preserve it as part of the Key West’s literary legacy. After completing a faithful restoration of the 1890s era eyebrow home, it now serves as the seminar’s headquarters with plans to host special events and cultivate the garden as a space open to the public. In one of Bishop’s most famous poems, “One Art,” her Key West home is one of the “three loved houses” whose loss she mourns. Thanks to the Key West Literary Seminar, it’s been found for all to remember.
Key West’s premier community playhouse, the Red Barn Theatre is situated inside a quirky former carriage house tucked away off Duval Street.
Red Barn Theatre
Key West’s premier community playhouse, the Red Barn Theatre is situated inside a quirky former carriage house tucked away off Duval Street. Since 1980, the company has brought lively plays to Key West, from world premieres to classics. Drawing from both local and visiting talent, every season brings a variety of dramas, comedies and musicals, including plays recently mounted on and off Broadway, from John Patrick Shanley’s Brooklyn Laundry to Larissa FastHorse’s The Thanksgiving Play. They also host visiting theater companies and entertainers. It’s a vital component of Key West’s creative community with acclaimed collaborators through the years including Shel Silverstein, former poet laureate Richard Wilbur and playwright Terrence McNally.
For a quirky piece of Key West history, stop by The Oldest House Museum & Garden on Duval Street.
The Oldest House Museum & Garden
For a quirky piece of Key West history, stop by The Oldest House Museum & Garden on Duval Street. The cottage dates back to 1829 and was built by Bahamian immigrant Richard Cussans. Built from locally sourced lumber in a manner typical of wooden ship building, this charming Bahamian-style cottage is emblematic of historic homes preserved throughout the island today. Inside, there’s a small museum with historic information about the home and a lovely garden. The foundation behind The Oldest House routinely hosts Key West Home Tours, including the Oldest House, itself, as well as historic gems across the island.
Overlooking the Gulf of Mexico and the channel with views of boats coming and going, it’s one of the most picturesque venues for live music.
Coffee Butler Amphitheater
The Coffee Butler Amphitheater is Key West’s newest performing arts venue. Debuting in 2017 as part of the newly redeveloped Truman Waterfront, you’ll also find the Florida Keys Eco-Discovery Center, a maritime museum aboard a historic Coast Guard vessel, a park with public art and a playground, all en route to Fort Zachary Taylor Historic State Park Beach. Named in honor of a local musician, Coffee Butler features both reserved seating and a general admission lawn for major concerts and events, including the annual Mile 0 music festival and Jimmy Buffett’s Coral Reefer Band. Overlooking the Gulf of Mexico and the channel with views of boats coming and going, it’s one of the most picturesque venues for live music.
Stock Island is home to several artist studios and galleries.
Stock Island Artist Studios
Just across the narrow Cow Key Channel from Key West, Stock Island is home to the area’s last working waterfront for commercial fisherman and shrimpers. It’s also home to several artist studios and galleries. While The Studios of Key West occasionally organizes guided tours, you can also embark on your own to visit. Anchoring the Stockyard Studios artist community, Stacey Hardy’s ClaySpace is a ceramics studio that offers classes, workshops and a space to create for ceramicists of all levels. Nearby, Washed Up is a woodworking studio and showroom by Kasidy Fritts, specializing in driftwood sculptures, reclaimed “upcycled” wooden furniture and fine art made of found materials. While in Stock Island, grab a bite at Bad Boy Burrito Taqueria & Tequila or The Docks, both creative locally owned spots whose cooking is an art form.
At the Tennessee Williams Museum on Truman Street, learn more about the playwright’s career and time in Key West through photographs, memorabilia and newspaper clippings.
Tennessee Williams Theatre
The Tennessee Williams Theatre has been an anchor of Florida Keys performing arts for over 40 years. Set on the campus of the College of the Florida Keys in Stock Island, the venue houses a 500-seat mainstage theater, as well as more intimate cabaret and black box theaters. As the largest theater in the Florida Keys, it hosts high profile touring acts, from country artist Kenny Chesney to humorist David Sedaris and modern dance company Pilobolus. It’s also a destination for classical music ensembles, from the South Florida Symphony Orchestra to Keys Choral Arts.
In the Upper Keys, Islamorada is home to a community of art galleries that have come together to create the Morada Way Arts & Cultural District.
Morada Way Arts & Cultural District
In the Upper Keys, Islamorada is home to a community of art galleries that have come together to create the Morada Way Arts & Cultural District. Take a stroll down the leafy lane just off US-1 near Mile Marker 81 and visit artist studios and galleries, including Jessica Ann Art, Taylor Hale Studio & Gallery and Morada Way Clay. The collective hosts Art Walks on the third Thursday of the month when the galleries stay open late and other vendors take to the streets to enjoy live music, food, drink and good times. Just up the Overseas Highway on the gulf side, another cluster of art galleries can be found, including Roberto Russel Galleries, Michelle Nicole Lowe and Seaside Glassworks.
