What's Up

What’s Up

So you’ve reached your final Florida destination, now what? Well, hold tight because this is one Florida destination where the fun never stops! In fact, there are probably more events and festivals going on in the Florida Keys & Key West than in any other Florida destination. Here’s a quick list of fun Keys’ happenings that you won’t want to miss!


The Aquanettes: Reality Is A Drag
Key West: Prepare yourself for some amazing costumes, great music and lots of laughs when the world famous Aquanettes take to the stage. This outrageous troupe of lip-synching, wise-cracking drag queens prance, dance, shimmy and shake to the hoots and howls of a packed house. No two shows are ever the same so you never know what’s going to happen. FYI: Bring lots of dollar bills for tipping the performers — the more you tip, the more they play. Showtimes: Sun – Weds at 9pm; Th at 7 & 9pm; Fri & Sat at 7, 9 &11pm. Reservations recommended. See them at Aqua Nightclub, 711 Duval St., Key West. Info: 305-294-0555; aquakeywest.com.

Christopher Peterson’s Eyecons
Key West: Often compared to the legendary Jim Baily, master of impersonations, Christopher Peterson is, without a doubt, one of North America’s foremost female impressionists, both visually and vocally. His hit show, EYECONS, is one of the hottest tickets in town and you’ll be totally amazed by the way he transforms himself into more than a dozen famous women right before your very eyes with the help of his “magic closet.” Catch him in the Crystal Room Cabaret at La Te Da, 1125 Duval St, Key West. Tickets and info: 305-296-6706; lateda.com.

Randy Roberts Live!
Key West: Spotlighted on television’s hit series “America’s Got Talent,” Randy Roberts absolutely shines in this live, multi-media tribute to some of the world’s most beloved performers. His uncanny impersonations of Cher, Bette Midler and Mae West are spot-on and he’ll have you rolling in the aisles when he performs a titillating strip tease as the bawdy Gypsy Rose Lee. But nothing compares to “Consuela,” Roberts’ own self-created character who can only be described as Ann-Margaret, Liza Minnelli and Joan Rivers all rolled into one powerhouse performer. Catch this amazing show at La Te Da’s Crystal Room Cabaret, 1125 Duval St, Key West. Tickets and info: 305-296-6706; lateda.com.

Key West Sunset Celebration

Key West: Each evening, about two hours before sunset, flocks of people gather at Key West’s Mallory Square and on the pier behind the Margaritaville Resort & Marina to watch the sun slowly sink into the Gulf of Mexico and to revel in the colorful street performers, local artists, psychics and food vendors who have made Key West’s Sunset Celebration a world-famous, multicultural happening. If you’re really lucky you may even witness the rare “Green Flash.” Experience it nightly at the end of upper Duval Street. Info: 305-294-2787; mallorysquare.com/sunset-celebration.

Jazz at Tavern N’ Town

Key West: Some of Key West’s top talent including “Island Diva” Carmen Rodriquez and Michael Thomas perform nightly from 5-7pm during Key West’s best Happy Hour. Takes place at Marriott Beachside Resort, 3841 N. Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.

Every Tuesday
Mario Sanchez Original Works & Lecture

Key West: Owner of Key West’s renowned Gallery on Greene, Nance Frank has curated multiple exhibits of famed Cuban artist, Mario Sanchez with catalogues for his exhibit pre-sented by The American Folk-Art Museum, The Museum of the City of New York, as well as Cuba’s National Museum. Her weekly presentation about Sanchez’s life and work is absolutely fascinating. Takes place at 2pm every Tues at the Gallery on Greene, 606 Greene St, Key West. 305-304-2323; galleryongreene.com.

Wednesday – Saturday
Cabaret in The Gardens

Key West: Key West’s Gardens Hotel is one of the most beautiful boutique hotels on the island and every Weds through Sat from 5 – 7pm, you can enjoy wonderful live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find at 525 Angela St, Key West. Info: 305-294-2661; gardenshotel.com.

Every Sunday
Jazz in The Gardens

Key West: Enjoy some terrific jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne and fabulous wines. Takes place from 5:30 – 8pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.

Third Thursday Morada Way Art Walk

Islamorada: Fine arts, live music and “culinary art” are the hallmark of this festive monthly event which showcases both national and local artisans in galleries along the Morada Way Arts & Cultural District. Takes place from 6 – 9pm on Old Hwy, MM 81.5, Oceanside, Islamorada. Info: 305-393-6012; moradaway.org.

First Friday MM 104 Block Party

Key Largo: Stroll among artists, shop for gifts, enjoy street bites from local eateries and more during this fun monthly Block Party. Takes place on the First Friday of every month from 6 – 10pm, rain or shine along the Overseas Highway at mile marker 104 in Key Largo. FYI: You can park at any of the MM104 businesses and walk along the bayside bike pathway. Info: keylargofirstfriday.com.

Every Third Saturday Native Plant Sale

Key West: Peruse over 2,000 native, rare and endangered plants from the Keys, Cuba and the Western Caribbean at this terrific monthly plant sale. Takes place from 9am – Noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.

September 1 – November 30
Fall Madness

Key West: Both kids and adult artists show off their seasonal art creations and compete for a host of prizes. Takes place daily from 10am – 4pm at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.

October 5
Chris Duarte

Key West: “Ferocious Blues” artist, Chris Duarte, is a savant, a sorcerer of tone, a master at channeling the spirits and sounds of great musicians of our past, while remaining completely recognizable in his own sound. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.

October 10 – 12
Peterson’s Harley Davidson Poker Run

Florida Keys: More than 10,000 riders from all over the U.S. rumble from Miami to the Keys, for a weekend of cruising and fun. Along the way, they make five stops and draw a card at each stop. The winner is the lucky guy or gal who draws the best hand. If you draw one of the top ten hands, you get a chance to play one round of Texas Hold ‘Em for the grand prize! This year’s run loops from Key Largo to Boondocks Restaurant in the Lower Keys. Info: 305-733-1008; petersonsharley.com

October 18 – 19
One Weekend Only

Marathon: This annual variety show and fundraiser is one of the Marathon Community Theater’s most fun events. For more deets and a complete list of events for the upcoming season, call 305-743-0094 or got to marathontheater.org. Located MM 49.5, Oceanside, (next to the Cinema) Marathon.

October 18 – 19
Bahama Village Goombay Festival

Key West: Historic Bahama Village transforms itself into party central with non-stop, live entertainment, island-style food, arts and crafts and a “Junkanoo Rush” of costumed marchers through Key West’s downtown at 6pm on Fri and Sat. Takes place from noon until midnight on Petronia Street. Info: 305-619-8989.

October 19
Coral Head Blues Fest

Marathon: Kick off the 2019 Fantasy Fest weekend with this newly added music event! Music acts such as Anthony Gomes, Dana Fuchs, Shaw Davis & the Black Ties, Bill Blue Band, Ghost Town Blues Band and Paul Delariers Band are to grace the stage from 11am to 10pm at Marathon Community Park’s amphitheater. Info: 305-743-4783; coralheadmusicfest.com

October 19 – 25
The Rocky Horror Show

Key West: That sweet transvestite and his motley crew are back for the Time Warp and it’s better than ever baby! On stage at the Waterfront Playhouse; 310 Wall St. Info and Tickets: 305-294-5015; waterfrontplayhouse.org.

October 19 – 28
40th Annual Fantasy Fest® Celebration

Key West: This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions including one for pets, a Headdress Ball, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats.Daily event schedule on pages 24 – 25. More info: 305-295-9112; FantasyFest.com.

October 20
10th Annual Zombie Bike Ride

Key West: This costumed, rock n’ Roll bike ride typically draws several thousand men, women and children — and even a few pets. Garbed in ragged costumes and frightening face and body makeup, they pedal along the island city’s Atlantic Ocean shore in a deliciously scary spectacle. The ghoulish event starts at 2pm when “Zombieland” opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd. Info: zombiebikeride.com.

October 24
37th Annual Headdress Ball

Key West: Get out your feathers, glue guns and ribbons for the Key West Business Guild’s annual fundraising extravaganza. Hosted by funny man, Tom Luna, this fantastical headdress competition includes special performances by renowned female impressionists, Christopher Peterson and Randy Roberts, Broadway star, Terri White and lots of other “over the top” entertainment. Gates open at 6:30pm. Showtime: 8pm. Held rain or shine. Takes place at the new Truman Waterfront Amphitheater. Always a sell-out so order tickets early Info: 305-294-4603; headdressballkeywest.com. Tickets: keystix.com.

October 26
10th Annual Screaming Green Halloween

Key West: Get your “ghoul on” at this all day kid – safe festival that includes workshops, face-painting, prizes, games, a costume contest, and more. Takes place from 10am – 2pm at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.

October TBD
Haunted 3rd Annual Fall Harvest

Marathon: Enjoy some old fashioned harvest time fun to celebrate the fall season! Hay rides, trail mazes, face painting, crafts for kids, burgers, chili dogs, apple cider, caramel apples, baked goods & live music. Takes place from 4 – 8pm at Crane Point Museum, Marathon Info: 305-393-9501; cranepoint.net.

November 3 – 10
38th Annual Key West World Championship Races

Key West: High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor, meaning smooth water where racers can achieve speeds above 140 mph and provide fans breathtaking displays of skill and power. Info: 305-296-6166.

November 4
Acoustic Alchemy

Key West: A night of live music and dancing featuring the Mambo and Cha Cha sounds of Havana along with Salsa, Merengue and Caribbean rhythm with Rolando Rojas & the All Star Band. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.


September 20 – 29
Island Hopper Songwriter Fest

Beaches of Fort Meyers & Sanibel: Jam out in Southwest Florida when some of the most talented, nationally acclaimed singer-songwriters return for this award-winning event. You can enjoy free shows at intimate venues on Captiva Island from Sep 20 – 22; Downtown Fort Myers from Sept. 23 – 26; and Fort Myers Beach from Sept. 27 – 29. Download the app and check out the 2019 lineup at IslandHopperFest.com.

October 11 – 13
10th Annual Oktoberfest Tampa

Tampa: Cited as one of the “Top 5” Oktoberfests in the US, this annual bash celebrates the season with German cheer, dancing and singing to cooler weather and colder beer along the Hillsborough River. Takes place on Fri from 4 – 11pm; on Sat. from 11am — 11pm; and on Sun from 11am — 6pm at Curtis Hixon Park, 600 N Ashley Dr, Tampa Info: oktoberfesttampa.com.

October 17 – 20
27th Annual Biketoberfest®

Daytona: Over 125,000 motorcyclists roll into the Daytona Beach area for this multi-day “fun fest” that includes motorcycle shows and rallies, live music, scenic rides, and racing at Daytona International Speedway. Lots of vendors, too, offering everything from the latest models to parts and accessories. Famous Main Street bars serve up great food and drinks, as well as live entertainment and giveaways. Info at Biketoberfest.org.