Everyone knows the Florida Keys have great places to escape to, whether you’re on vacation, having a staycation, or just looking for a fun activity. Beyond the sun, surf, and sand, Southern Florida has strong historical roots that are still a part of the Keys today. The rich cultural and social background intertwines with the history but has made a name all its own. From the famous festivals to the shows going on around the city, it’s something to see. The best part of the scene down here? You really can’t go wrong. We’ve curated our top ten fun things to check out to save you some time. Or, if you know someone visiting, show them our list!
Annual October Event
Fantasy fest returns this year, and the theme is ‘cult classics’ and ‘cartoon chaos.’ For those that don’t know, FF has become a cultish event that pulls in around 75,000 costumer and fun fanatics a year. Held annually during the last two weekends of October–closest to Halloween–have more than 60 events. It has something for any attendee–glamorous balls, costumed marches, street fairs, and even the epic one-of-a-kind Fantasy Fest parade. Sound too good to be true? All of the activities' proceeds are structured to raise money and aid local non-profits.
Initially formed by a small group of local shop owners, the idea of the festival was to drum up some revenue at the beginning of the off-season. Many local businesses had ended up with ‘gone fishin’ signs and were closed for the season before the festival’s inception. In 1979, The quartet of owners, Bill Conkle, Tony Falcone, Joe Liszka, and Frank Romano, ran with it and changed the historic Bahama Village’s scene forever. If you want to check it out, it started this past Friday, the 21st, and runs through October 30th.
Tour Art in Public Places
Throughout the Keys
The simplest, but maybe one of the most fun things, available year-round and, best of all, free, is to check out all the public art throughout the city. The Florida Keys Council of the Arts created this project and has commissioned art on any new major construction within county limits. The project, heading into its second decade, has completed projects on The Roth building, the Freeman Justice Centers, and the Murray E. Nelson Government & Cultural Center, to name a few. Check out The Florida Keys Council of the Arts Public Arts webpages for listings of all sites. Future sites for new installations include Bernstein Park, marathon Court House, the Freeman Justice Center’s lobby expansion, and the Drug Court’s renovations.
The Gates Hotel, Key West
May 26-29, 2023
The beloved festival returns this May. It runs during Memorial day weekend this coming year at the Gates Hotel on the Sunset Green Lawn. A local must and haven, the Key West Whiskey fest offer different tastings, whiskey walks, workshops, and brunches–when you need refueling.
The fest brings in a diverse and fun crowd ready to partake in all things whiskey. An array of bourbons, Irish whiskeys, and others will get showcased from many different distilleries, including local favorites, Key West Trading Co., Slane distillery from Meath, Ireland, and Uncle Nearest of Tennesee.
Randy Roberts at La Te Da
Lower Duval Street
Check La Te Da’s Event Schedule
With his impressive impersonations, Randy Roberts is headlining the Crystal Room of the La Te Da, a multifaceted hotel, restaurant, bar, and cabaret establishment. The show centers around his tributes to legendary ladies in show business, ranging from divas like Cher and Bette Midler to funny ladies like Carol Channing and Phyllis Diller, and many more, including a slew of original characters. You won’t want to miss this one-woman show! Randy is renowned nationally and has had roles on a few tv shows and performed on America’s Got Talent. For showtimes, make sure to check out La Te Da’s schedule page.
The Oldest House Museum
Duval Street, Key West
Year-Round (closed Wednesdays and Sundays)
Built-in 1829, the oldest house and cookhouse in Key West is not something to miss! The home was constructed with wood by Richard Cussans, an immigrant from the Bahamas who came to Key West the previous year. Cussans original plot was on Whitehead Street but has since moved and now stands at 322 Duval. You can go check out the house five days a week–closed on Wednesdays and Sundays–from 10-4. Both structures boast period interiors with volunteers and staff members on-site to aid or answer questions. Admission is $10 and a discounted price for military and seniors.
The Old Island Restoration Foundation has continued the preservation of Cussan’s house and other parts of historic Key West. Currently, they are celebrating their 200th anniversary, and if you’d like to aid in continuing the conservation, they are selling 200 bricks, one for $200.
Don’t miss their Annual Home Tours November - March!
History of Diving Museum
Mile Marker 83 Overseas Highway, Islamadora
Year-round (seven days a week)
The Diving Museum of Islamorada has dedicated its mission to preserving the history of diving and educating the public by showcasing its artifacts, books, antiques, photos, and other recorded materials. Their collection boasts both international and local histories of diving, and their mission is to celebrate and share the evolution of the history of diving. Visiting hours are daily from 10-5, and tickets range from $7 (children) to $15 (adults) and have discounted prices for seniors, veterans, active military, students, historical diving society members, and NARM and SNAP recipients.
Take a class at The Studios of Key West
Simonton & Eaton, Downtown Key West
Year-round (closed Sundays and Mondays)
The Studios of Key West offer an array of classes for anyone. With over 50 types of courses available in person and online, everyone is welcome to try their hand at an activity. The studios have played host to Pulitzer prize winners, internationally acclaimed artists, and musicians. Steps away from Duval, there’s no reason not to check it out! Whether you’re interested in picking up a new hobby, refining your craft, or curious, look at their schedule and try a few options! You’ll be able to find either option for online or in-person classes.
Check out their website for exhibits and events while you are there!
The Waterfront Playhouse
Mallory Square, Key West
October 2022-June 2023
Entering its 84th season, the Waterfront playhouse is a cultural must while in Key West! Located in Mallory Square, the playhouse has been putting on shows like The Rocky Horror Show, Hair, Young Frankenstein, Monty Python’s Spamalot, and Twelve Angry Men, to name a few.
The Keys has attracted globally recognized talent with its own local diverse community of industry vets. The Waterfront, run as a non-profit, has a dedicated fanbase of locals and tourists that continue celebrating and preserving this beautiful playhouse. Upcoming shows include Jimmy Buffett’s Escape to Margaritaville, Rock of Ages, and Full Committed.
Morada Way Arts Fest
Morada Way Arts & Cultural District, Islamorada
Every Third Thursday
Located in the upper Keys, Islamorada, Morada Way Arts Festival is put on every third Thursday of the month from 6-9 pm. Run by the Morada Way Arts & Cultural District (MWACD), a non-profit, has been giving local artists a place to share their art and patrons, both residents and tourists, a place to support the local art scene since 2011. The fest also hosts specific events and cultural activities that vary monthly. The fest just happened, so you’ll have to wait until November to check it out, but take a look at their site in the meantime and find some favorite artists to find! And, if you’re an artist looking to share your art, take a look at their page. The fest is always accepting vendor submissions.
Art in the Key West Tropical and Botanical Gardens
Finally, look at the art in the garden at the botanical gardens near Stock Island. Open daily, the exhibit and gardens coexist, and all of the artists' submitted pieces consist of recycled, natural, or repurposed items. Operational since 1936, the Key West Botanical Garden is the “only frost-free, sub-tropical, natural conservation habitat, native plant botanical garden in the continental United States.” As an educational non-profit charitable corporation formed during the Depression Era as a part of the recovery efforts of the time. Admission to see the beautiful gardens and eclectic art is free for members and children, $10 for adults, and $7 for seniors.
We hope you’ve found some inspiration or direction in your future plans to spend time in the Florida Keys! Or that our list has convinced you to come and visit any part of these islands. Make sure to bring a good friend or loved one to experience it–and show off what you learned from this article. Regardless of your path while exploring, there are memories and lots of fun to be had throughout the year. Just make sure to bring some sunscreen and a hat!