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!


Jazz at Tavern N’ Town

Key West: Some of Key West’s top talent including “Island Chanteuse” 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.

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. Experience it nightly at the end of upper Duval Street.

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 presented 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.

Fourth Wednesday Potluck

Key West: The Studios of Key West hosts a casual potluck at the residency guesthouse “In the Courtyard” to welcome their newest Artists in Residence. Just bring an appetizer, salad, main dish, dessert or snack and TSKW will supply the drinks. Takes place from 6 – 8pm in the covered courtyard at the Carriage Trade Artist Residency House, The Studios Of Key West, 533 Eaton St, Key West. Info: 305-296-0458; tskw.org.

First Thursday Art & Shopping Walk

Key West: On the First Thursday of each month, The Studios of Key West (TSKW), along with many other neighboring galleries in the 500 Block of Fleming St, host special exhibitions from 6 – 9pm. On Dec 5, TSKW hosts Cuban artists, Osmeivy Ortega, Lisandro Ramirez, & Silvia Rivero, from 6 – 8pm and continues the exhibit through Dec 26; Outside the Lines, the Winter Members Exhibition, opens on Dec 5 from 6 – 8 at TSKW and continues through Dec 26; Najide Shabaka, Donna Nadeau & Jim Ranchin premiere at TSKW on Jan 2 from 6 – 8pm and will show through Jan 25. More info: 305-296-0458; tskw.org.

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.

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.

Fourth Saturday

Snook’s Luau & Pig Roast
Key Largo: Swivel your hips and feast like a king during this monthly tropical extravaganza that boasts fire dancers, hula dancers, great live music and continuous live entertainment that will keep you jumpin’ all night long. The party kicks off at 6:30pm on Sat, Nov 30 and Sat, Dec 28. Sells out fast so be sure to make reservations. Takes place on the waterfront at Snook’s Bayside & Grand Tiki, MM 99.9, Bayside, Key Largo. Info: 305-453-5004; snooks.com.

January 9 – 19
Uncorked Food & Wine Festival

Key Largo/Islamorada: Culinary experts step up to the palate for ten glorious days of food, wine and spirited events where you can enjoy wine tastings and dinners, cooking demos, food and wine pairing classes, art and wine shows, a Gospel Brunch and the Florida Keys’ famous “Chopped” Charity Event. Info: 305-522-1300; floridakeysuncorked.com.

January 17
Tommy Castro

Key West: Whether he’s squeezing out the deepest blues or playing the funkiest soul grooves, legendary blues and soul giant Tommy Castro knows how to ignite a crowd. Doors open 7pm; Showtime 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.

January 17 – 18
60th Annual House & Garden Tours

Key West: The annual Key West Home Tours™ are one of the oldest and longest running home tours in America and features five lovely homes and gardens on each day’s tour. Each stop reflects the varied tastes and originality of its owners. This year the tour includes a Bonus 6th Stop at historic inns/hotels that will feature free drinks and nibbles. Takes place from 3 – 6pm and proceeds benefit the Old Island Restoration Foundation. Tickets and schedule available online at OIRF.org. Info: 305-294-9501.

January 17 – 19
8th Annual Baygrass Bluegrass & Craft Beer Festival

Islamorada: This weekend-long festival kicks off in “downtown” Islamorada on Fri, Jan. 17 with a celebration along the Morada Way Arts & Cultural District. On Sat, Jan 18, a fun Pickin’ Party & BBQ starts at 5pm in Founders Park. The main concert, which happens on Sun, Jan 19 from 11am – 8pm, features a terrific blend of great Bluegrass music as well as a Craft Beer Garden and arts & crafts vendors. Info: baygrassbluegrass.com.

January 18
37th Annual Art Under The Oaks

Tavernier: Fine art & original crafts, specialty food booths and a great raffle make this a fun, family friendly event. Takes place from 9am – 4pm at San Pedro Church Gardens, MM 89.5, Tavernier. Info: 305-664-0888; sanpedroparish.org.

January 18 – 19
15th Annual Florida Seafood Festival

Key West: Lots going on for both adults and kids from feasting on fresh local seafood and shopping for marine-related crafts, to face painting, kids hands-on activities, raffles and live music. Takes place on Sat from 11am – 8pm and on Sun from 11am – 5pm in Bay View Park at 1320 Truman Ave. Info: 305-619-0039; floridakeysseafoodfestival.com.

January 25 – 26
35th Annual Key West Craft Show

Key West: This juried, nationally recognized outdoor craft festival attracts over 100 fine and skilled artists who showcase their beautiful pottery, fabric, glass, wood, jewelry and other colorful handmade works. Takes place from 10am – 5pm along Whitehead St from Greene St to Eaton and on Caroline St at Truman Annex in Key West. Info: 305-294-1243.

January 26 – February 2
Key West Food & Wine Festival 2020

Key West: Celebrate the local culinary arts community and enjoy lots of lively events all over the island including a Welcome Beach Party, Wine Dinners, Shrimp Boil, Wine & Food Seminars, Bad Ass Brunches, “Duval Uncorked,” Neighborhood Wine Strolls, Grand Tasting and much more. Info: 305-292-1622; KWFoodWineFest.com.

January 26
Annual Schooner Wharf Wrecker’s Cup Race

Key West: This is the first leg of the spirited 7 mile race to Sand Key where bragging rights is top prize. Race kicks off at 1pm with an Awards Ceremony at 7pm. Takes place at Schooner Wharf Bar in Key West’s Historic Bight. Info: 305-292-3302; schoonerwharf.com.

January 26
26th Annual Master Chefs Classic

Key West: Local chefs go head to head as they compete for best of the best in Appetizer, Entree and Dessert categories as they provide an amazing array of incredible food for those who are lucky enough to snag tickets. This event always sells out early and is a fundraiser for the MARC House. Takes place from 4 – 7pm at Margaritaville Key West Resort & Marina, 245 Front St. Info: 305-294-9526; masterchefsclassic.com. Tickets: keystix.com.

January 28 – February 1
3rd Annual Mile 0 Festival

Key West: This island-wide festival stages an early Kick Off Party on Tuesday, January 28 with a free concert on Duval Street. Subsequent concerts take place on numerous stages throughout Key West. Info: mile0fest.com.

February 4
Joan Osborne

Key West: As one of the great voices of her generation, this multi-platinum selling recording artist and seven-time Grammy nominee is renowned for her gritty blues-based rock. Doors open 7pm; Showtime 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.

February 9
Songwriter Speakeasy Series: Gary Hemsey, Dan Holberg, Joel Nelson

Key West: One of Key West’s best kept secrets, this monthly series showcases local songwriters who perform their original works and tell the stories behind the songs. Doors open 6:30pm; Showtime 7pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.

The Florida Keys and Key West are home to a thriving performing arts community which stages world class theater, dance and concert productions from Key West to Key Largo. Historical luminaries including playwright Tennessee Williams, novelist, Ernest Hemingway and poet Robert Frost, created some of their best works here and that tradition continues to-day as more and more writers, artists, musicians, dancers and performers flock to our small piece of paradise from all over the world.

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 rec-ommended. 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, Christo-pher 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.

Fringe Theater Of Key West
Key West: Key West is uniquely rich in historical and unusual venues and this “immersion theater” troupe literally “takes you places,” by performing unconventional shows in intimate settings that suit each play. Fringe creates theater that is light on its feet, reflects a variety of theatrical voices and is also affordable. For this season’s exciting lineup, tickets and more info: 305-707-4053; FringeTheater.org.

Impromptu Concerts
Key West: On Jan 12, award-winning pianist, Blake Pouliot, kicks off Impromptu’s 2020 season with a masterful performance you won’t soon forget. Trio Gaspard, whose members are from Germany, Greece and the UK and is one of the most sought-after trios of its genera-tion, takes to the stage on Jan 26 followed by the Canellakis-Brown Duo, two highly ac-claimed artists who perform on Feb 9. The 4pm Sunday afternoon concert series takes place at St. Paul’s Episcopal Church, 401 Duval St, Key West. Tickets available at the door or at keystix.com. Info: keywestimpromptu.org.

Key West Theater
Key West: Originally built in 1848 as the 1st Baptist Church of Key West, this newly reno-vated performing arts center is home to a Community Stage, Rams Head Promotions, Grate-ful Guitar, Back Stage Listening Room and the Key West Theater Recording Studio. It’s the place to go for top tier music, concerts, comedy & variety specials as well as locally pro-duced Key West events. Located at 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.

Marathon Community Theater
Marathon: With just two actors, twenty characters and a barrel of laughs, Greater Tuna, is a hilarious send-up of small-town morals and mores in Tuna, Texas – the state’s third-smallest town. Opens on Thurs, Nov 14 at 8pm and plays through Sat, Dec 7 with a matinee on Sun, Dec 1 at 3pm. Four Old Broads, a laugh-out-loud comedy about a retired burlesque queen and her cohorts at an assisted living facility, opens on Thurs, Jan 16 and runs through Sat, Feb at 8pm with a matinee on Sun, Feb 2 at 3pm. On Fri, Feb 21 and Sat, Feb 22 at 8pm, MCT presents a special reading of the American Classic, True West by Sam Shepard. Located MM 49.5, Oceanside, (next to the Cinema) Marathon. Tickets and info: 305-743-0094; marathontheater.org.

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, Better 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 which 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.

Red Barn Theatre
Key West: The Red Barn Theatre kicks off its 40th season on Tues, Dec 10 with the opening of “Tiny Beautiful Things” a hilarious and heart-warming tale about an anonymous online columnist who doles out her own particular brand of brutal honesty and incisive empathy. Catch it through Sat, Jan 4. On Tues, Jan 14 through Sat, Feb 8, Life Sucks when a group of old friends, ex-lovers, estranged in-laws and lifelong enemies gather to grapple with life’s thorn-iest questions—and each other. Frankie and Johnny In The Clair De Lune, a sometimes touching, sometimes hilarious interplay about the promise of a relationship evolving beyond a “one-night stand” takes to the stage on Tues, Feb18 through Sat, March 14. Showtimes 8pm. Located at 319 Duval St, Key West. Info and tickets at 305-296-9911; redbarntheatre.com.

Waterfront Playhouse
Key West: The Waterfront Playhouse kicks off its 80th season with The Informer, a timely story about a teacher and his wife who are terrified that their son, a fanatic member of the Hitler Youth, will denounce them for their critical comments about the regime. On stage Sun and Mon, Nov 3 and 4 and again on Sun and Mon, Nov 10 and 11 at 7pm. Hair In Concert, the international musical hit that changed the sound and the face of the Broadway musical opens on Fri, Nov 22 and plays through Mon, Nov 25. Stampeding elephants, raging typhoons and runaway trains star in Around the World in 80 Days, an unabashedly slap-stick about one amazing race. Opens Thur, Dec 12 at 8pm and plays through Sat, Dec 28 with a special preview on Wed, and Thurs, Dec 11. The world premiere of Glass, explores what happens when the legendary Tennessee Williams and actress Laurette Taylor meet backstage on the opening night of The Glass Menagerie. Opens on Thur, Jan 16 at 8pm and plays through Sat, Feb 1 with a special preview on Tues, Jan 14 and Wed, Jan 15. Lady Day at Emerson’s Bar & Grill, a salty, often humorous take on one of Billie Holiday’s last performances in 1959, opens on Wed, Feb 12 at 7pm and lights up the stage through Sat, Feb15. Located at 310 Wall St, Key West. Tickets and info: 305-294-5015; waterfrontplayhouse.org.

Other Florida Happenings

“Climb to the Moon” at Ponce de Leon Lighthouse
Daytona: Once each month during a full moon, you can climb to the top of the 175’ Ponce Inlet Lighthouse and experience spectacular views of the sunset and moonrise. Toast the setting sun with a sparkling beverage, enjoy tasty hors d’ oeuvres and revel in the panoramic vistas of the ocean, inlet, and inland waterways under the brilliant light of the full moon. For a real treat, you can join the lighthouse keeper for a journey into the past and discover the unique history of this National Historic Landmark which has been a Florida Coast beacon for more than 130 years. Limited to 25 participants. Tickets must be purchased in advance. Info and reservations: 386.761.1821 ext. 10; admin@ponceinlet.org. Find it at 4931 S. Peninsula Drive, Ponce Inlet, FL 32127. ponceinlet.org.

January 11 – 12
35th Annual Cape Coral Arts & Music Festival
Cape Coral: Now in its 35th year, this highly anticipated festival showcases the works of more than 300 juried artists and artisans. An array of vendors also offer a wide variety of food & beverages, as well as live music. Admission and parking are free. Takes place on Cape Coral Pkwy, Cape Coral. Info: CapeCoralFestival.com.

January 18 – 19; Jan 25 – 26 & 31; & February 1 – 2
34th Annual Hoggetowne Medieval Faire

Gainesville: For three magical weekends, the Alachua County Fairgrounds transforms into “Hoggetowne” – a medieval marketplace where you can immerse yourself in the rich culture of the Middle Ages. Open Jan 18 -19 and Jan 25 – 26 from 10am – 6pm; Jan. 31from 9:30am – 4:30pm; and on Feb 1- 2 from 10am – 6pm. Find it at 3100 NE 39th Ave. in Gainesville. Info: HoggetowneFaire.com.

February 1 – 2
ArtFest Ft. Myers

Fort Myers: Artfest kicks off with Friday Night Opening Party on Jan 31and features many festival artists under the stars from 6 to 10pm. On Sat and Sun, you can enjoy the works of 200 outstanding professional artists from across the country, as well as a high school art competition, art demos, children’s craft area and a sidewalk chalk extravaganza. Free admission and plenty of parking. Takes place from 10am – 5pm. Info: ArtFestFortMyers.com.