Hemingway, Buffett & the Florida Keys’ Big Anniversary Year
The Florida Keys have always been a place where history runs as deep as the surrounding seas. In 2026, that history is very much worth celebrating, from a Cuban heritage institution that has stood for 155 years to a beloved grocery store where Jimmy Buffett fans still make pilgrimages for chocolate milk. Whether you're drawn to the legends of Hemingway, the songs of Buffett, the resilience of sea turtles, or simply the best mojito in Key West, this is a landmark year up and down the island chain. Here's a look at the milestone anniversaries that make 2026 an especially meaningful time to visit — and to raise a glass.
The current home of the 155-year-old San Carlos Institute is located on Key West's Duval Street. Photo Credit: JoNell Modys
155th Anniversary
San Carlos Institute
The San Carlos Institute is a Cuban heritage center founded in 1871 by Cuban exiles who came to Key West to plan the campaign for Cuba's independence from Spain. One of the original locations for the Institute was destroyed by fire and another in a hurricane. The current location on Duval Street opened in 1924 and has served as a shrine to Cuba’s heritage and now hosts many cultural and artistic events
After an extensive renovation, the 100-year-old La Concha is now part of Marriott’s Autograph Collection. Photo Credit: La Concha
100th Anniversaries
La Concha
The La Concha, the hotel once known as the “Grande Dame of Key West” and that is now a Marriott Autograph Collection property, is celebrating its 100th anniversary, having opened on January 22, 1926. In conjunction with the centennial, the recently renovated hotel is celebrating with a year-long series of events and initiatives that strengthen ties to the Key West community, including a partnership with local nonprofit Reef Relief. The Tropicado bar in the hotel’s lobby features live Latin music on Friday and Saturday nights and has been recognized as having the best mojito on the island.
Fans of Buffett make pilgrimages to Fausto’s Food Palace in search of chocolate milk thanks to a famous mention in a song from his Key West days. Photo Credit: JoNell Modys
Fausto’s Food Palace
In 1926, Cuban-born Fausto Castillo opened a small grocery store in Key West that he ran alongside his wife, Ana Luisa Alvarez. They had a daughter, also named Ana Luisa, who worked at the store and took over for her mother when she passed away. She married Carl Weekly, a Navy man stationed in Key West, who was also a trained meat cutter. Their sons Jimmy and Alton now manage the two Key West locations of Fausto’s as they celebrate its 100th anniversary. The store is a legendary stop for visiting Parrotheads (dedicated fans of Jimmy Buffett) who come to the store in search of chocolate milk. That’s thanks to a line in Buffett’s song “My Head Hurts, My Feet Stink and I Don’t Love Jesus,” in which he mentions “going down to Fausto’s, get some chocolate milk” as part of a hangover cure.
An indigo bunting makes a migration rest stop at the Key West Tropical Forest & Botanical Garden. Photo Credit: KWTFBG
90th Anniversary
Key West Tropical Forest & Botanical Garden
The 15.2-acre Key West Tropical Forest & Botanical Garden celebrates 90 years in 2026, (opened Feb. 23, 1936) and is the only frost-free botanical garden in the continental U.S. The 15.2-acre site has two of the last remaining freshwater ponds in the Keys and is a major migratory stopping point for north and southbound birds. It’s also home to many rare birds, animals and plants that are native to the Florida Keys. The garden is renowned as a tranquil escape for residents and visitors that is filled with quiet beauty.
The Islander Resort is famous for its fishing pier and expansive Atlantic ocean shoreline. Photo Credit: The Islander Resort
75th Anniversary
The Islander Resort
The Islander Resort opened in 1951 in Islamorada and celebrates its 75th anniversary in 2026. Chicago attorney and avid fisherman Leo Samuels established the property with a dream of creating a tranquil, family-focused escape. Situated along 1,100 feet of coral-sand shoreline, the resort embraced the Mid-Century Modern aesthetic, including its now-iconic “Space Age” sign—a bold emblem of 1950s optimism and innovation. Recent updates honor its history while enhancing the guest experience with modern comforts, sustainable practices, and reimagined amenities. Islander remains a place where generations connect, inspired by the timeless beauty and essence of the Florida Keys.
Mrs. Mac’s Kitchen in Key Largo has two locations in Key Largo that are favorite stops for locals and visitors.
50th Anniversaries
Mrs. Mac’s Kitchen
Mrs. Mac’s Kitchen, with two locations in Key Largo, celebrates 50 years of cooking and serving beloved and award-winning dishes to countless visitors and devoted locals. The first Mrs. Mac’s Kitchen was established in 1976 by Jeff MacFarland and was named after his mother. It also featured many of her fabulous recipes. He hired a cook named
Angie in 1987, soon followed by her sister, Paula. Angie bought the restaurant and ran it for 35 years, adding the second larger location just down the road from the original bayside location. In 2023, Stephanie Figueroa took over as the new owner, maintaining the laid-back vibe and traditional recipes, including the award-winning Key lime pie.
The Marathon Seafood Festival features fresh local catch of fish, lobster and stone crab claws plus live music and more every March. Photo Credit: JoNell Modys
Marathon Seafood Festival
Founded in 1976 by Gary Graves and Gwen Collins, the first Marathon Seafood Festival was an impromptu gathering at a local bar to promote Middle Keys fishermen and their catches, held in the parking lot that is now home to the Marathon Publix. What started as a small get-together now brings as many as 20,000 attendees to Marathon Community Park each year in March. The event continues to be staged by the Organized Fishermen of Florida (Marathon Chapter) and the Greater Marathon Chamber of Commerce. To this day, the seafood is all caught, cleaned and prepared by fishermen and their families, along with homemade desserts including Key lime pie.
Jimmy Buffett and his Coral Reefers Band played a concert on an unusually cold and windy January evening in 1976 at Mallory Square in support of the Havana Daydreamin’ album. Photo Credit: Lawson Little
Jimmy Buffett’s Album Havana Daydreaming
2026 is the 50th anniversary of the 1976 release of Jimmy Buffett’s Havana Daydreamin’ album, his most successful album release to date at that point in his career. Buffett and his newly formed Coral Reefer Band played at numerous locations around Key West that year to support the album, including a legendary cold and windy January concert in Mallory Square. Songs on the album include Havana Daydreamin’; Woman Goin’ Crazy on Caroline Street; Cliches; My Head Hurts, My Feet Stink and I Don’t Love Jesus; Kick it in Second Wind; the Captain and the Kid and others.
Tim Stockwell of Key West was earned the coveted “Papa” title at the annual Hemingway Look Alike Contest in 2025. Photo Credit: Florida Keys News Bureau
45th Anniversary
Hemingway Days Festival & Look-Alike Contest
One of Key West’s most iconic signature events celebrates 45 years in 2026 – the Hemingway Days Festival and Look-Alike Contest. Created by Michael Whalton, then-manager of Hemingway’s beloved hangout, Sloppy Joe’s Bar, the festival got its start as a promotional stunt. Over the decades, contestants have traveled from all over the world to compete. Known as the “Papas,” they often dress in heavy wool sweaters and turtlenecks such as those favored by Hemingway in his later years. Previous winners serve as judges to evaluate each year’s crop of contenders, who appear in several contest rounds on stage at Sloppy Joe’s. The festival also includes the annual “Running of the Bulls,” a wacky spoof of the famous Pamplona, Spain festival. Key West’s version features wooden “bulls on wheels” that are paraded through the streets by the Papas.
A rehabilitated sea turtle is returned to its ocean home by The Turtle Hospital team. Photo Credit: Florida Keys News Bureau
40th Anniversary
The Turtle Hospital
The Turtle Hospital opened in 1986 in Marathon (Middle Keys) with the goal of healing injured sea turtles and returning them to their ocean home. The facility became the world’s first licensed veterinary hospital for sea turtles. Upon the hospital’s 40th anniversary in 2026, the facility and its dedicated team has treated and released more than 3,000 threatened and endangered sea turtles. Many thousands of visitors tour the hospital each year and can symbolically adopt a turtle to help support its care.
A live concert at Ocean Key Resort’s Sunset Pier kicked off five days of performances across Key West during the 30th annual Key West Songwriters Festival in 2026. Photo Credit: Carol Tedesco/BMI
30th Anniversary
Key West Songwriters Festival
The Key West Songwriters Festival is well-established as one of the largest and most well-produced songwriter festivals anywhere. Spanning five days each spring, it brings over 250 hit-makers and emerging artists to the island to perform acoustic “in the round” shows where the creative minds behind top country, Americana and pop hits share the stories being their songs. The entire island transforms into a festival venue with a free concert on Duval Street and many scheduled and popup appearances by singer-songwriters, some ticketed, as well as many free appearances at restaurants, hotels, bars and other venues.
