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!

Mallory Square & Margaritaville Resort 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 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.

Jazz At Tavern N’ Town

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

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 catalogs 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 2 pm every Tuesday at Gallery On Greene, 606 Greene St, Key West.Contact: 305-304-2323; galleryongreene.com.

Third Thursday Morada Way Art Walk

Islamorada: Fine arts, live music and “culinary art” is 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 – 9 pm on Old Hwy, MM 81.5, Oceanside, Islamorada. Info: 305-393-6012.

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 – 7 pm, 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.

First Friday
MM 104 Block Party

Key Largo: Stroll among artists, do some gift shopping, 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 – 10 pm, rain or shine along the Overseas Highway at mile marker 104 in Key Largo. You can park at any of the MM104 businesses and walk along the bayside bike pathway. Info: keylargofirstfriday.com.

Every Saturday & Sunday
Big Pine Flea Market

Big Pine Key: Discover all kinds of great finds at unbeatable prices at this long-time Lower Keys Flea Market that showcases an eclectic mix of both used and new merchandise, as well as locally made soaps, tools, and tarps, fishing supplies, watches, and jewelry, fresh seafood and produce, homemade ice cream and special Pop-Up stores. Open from 8 am – 2 pm every Sat and Sun through July. Free admission and parking. Find it at 30250 Overseas Hwy, Oceanside on Big Pine Key. Info: 305-872-4103.

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 – 8 pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.

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 6:30 pm on Sat. Nov 24, Sat, Dec 29, Sat, Feb 23, Sat March 23 and Sat, April 20. 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.

Fort Taylor Living History Weekend

Key West: On the third weekend of each month, Fort Taylor Zachary Taylor Historic State Park is transformed into a Union-occupied encampment where local and regional re-enactors portray life as it was in 1861, during the American Civil War. Firing and cooking demonstrations are all part of the excitement as you embark on a trip through time to see, hear, and smell what life was like in a Federal Fort during the War. Takes place from 10 am – 2 pm at Fort Zachary Taylor Historic State Park, 601 Howard England Way Key West. Info: floridastateparks.org.

January 10 – 20
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: 305-394-3736; floridakeysuncorked.com.

January 18 – 19
59th Annual House & Garden Tours

Key West: Festively dressed Key West homes and gardens take center stage during this much anticipated self-guided tour that showcases exquisite restorations, creative renovations, and delightful interiors and exteriors. The tours take place from 3 – 6 pm and proceeds benefit the Old Island Restoration Foundation’s museums, collection and education, grant, and scholarship programs. Tickets and schedule available online at OIRF.org. Info: 305-294-9501.

January 18 – 20
7th Annual Bluegrass & Craft Beer Festival

Islamorada: This weekend-long festival kicks off in “downtown” Islamorada on Fri, Jan. 18 with a celebration along the Morada Way Arts & Cultural District. On Sat, Jan 19, a fun Pickin’ Party & BBQ starts at 5 pm in Founders Park. The main concert, which happens on Sun, Jan 20 from 11 am – 8 pm, features a lively blend of great Bluegrass music. Takes place at Founders Park, MM 87 Bayside. Info: baygrassbluegrass.com.

January 19
36th Annual Art Under The Oaks

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

January 19 – 20
14th 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 11 am – 8 pm and on Sun from 11 am – 5 pm in Bay View Park at 1320 Truman Ave. Info: 305-619-0039; floridakeysseafoodfestival.com.

January 23 – 27
Key West Food & Wine Festival

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; keywestfoodandwinefestival.com.

January 26 – 27
34th 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 10 am – 5 pm along Whitehead St from Greene St to Eaton and on Caroline St at Truman Annex in Key West. Info: 305-294-1243.

January 28
Annual Schooner Wharf Wrecker’s Cup Race

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

January 29
25th 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 at 7 pm at Margaritaville Key West Resort & Marina, 245 Front St. Info: 305-294-9526; masterchefsclassic.com. Tickets: keystix.com.

February 2 – 3
25th Annual Pigeon Key Art Festival

Marathon: World-renowned marine life artist and conservationist, Wyland, headlines this open-air, juried show which features original paintings, crafts, sculptures, pottery and other works by dozens of highly acclaimed artists from across the US. Takes place from 10 am – 5 pm at Marathon Community Park, MM 49, Oceanside. Free parking and shuttle service from 33rd St. Info: 440-477-7203; pigeonkeyartfestival.com.

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: Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is absolutely impeccable. Peterson’s highly acclaimed show, EYECONS is All Live, no lip-sync and his transformations from icon to icon right in front of your eyes (aided by his magic closet on stage) is simply amazing. Be prepared to be blown away by his parodies Bette Midler, Tina Turner, Liza Minnelli, Judy Garland, Cher Lucille Ball, and now even Lady Gaga. This is one show you don’t want to miss and one the whole family can enjoy (well, the Adams Family, anyway!). 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’s “immersion theater” troupe literally “takes you places,” by performing in intimate venues that suit each play. Broadway star, Terri White, performs on Thurs, Dec 27 – Mon, Dec 31 at the Little Room Jazz Club. On Tues, Jan 22 – Sat, Feb 2, two writers grapple with betrayal in “Collected Stories” at the Key West Women’s Club. “The Piano Lesson,” plays on Fri, Feb 15 – Sat, Feb 16 at a location yet to be determined. On Tues, March 12, Lee Roy Reams brings his popular New York revue for one night only at the Tropic Cinema. Tickets and more info: 305-731-0581; fringe theater.org.

Impromptu Concerts
Key West: On Sun, Jan 13, classical organist and improvisational artist, Chaz Bowers gives a masterful performance of music that is designed to inspire. On Sun, Jan 27, award-winning violinist, Timothy Chooi, one of Canada’s most promising and exciting artists shares his musical prowess with a powerful performance you won’t soon forget. The Camerata Ensemble, a unique group, comprised of members of Amsterdam’s renowned Royal Concertgebouw Orchestra performs on Sun, Feb 17 with music by Mozart, Mendelssohn, Corelli, and Mahler. The 4 pm Sunday afternoon concert 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.

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 striptease as the bawdy Gypsy Rose Lee. But nothing compares to “Consuela,” Roberts’ 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
The Red Barn Theatre kicks off its 39th season on Tues, Dec 11 with the opening of “With Bells On,” a hilarious and heart- warming tale about an uptight accountant and a drag queen in full Christmas Queen Pageant regalia who get stuck in an elevator together. Catch it through Sat, Jan 5th. Back by popular demand, “Short Attention Span Theatre 2019” opens on Tues, Jan 15 and showcases an all-new, high-octane collection of fun, 10 minute plays. On stage through Sat, Feb 9. On Tues, Feb 19 through Sat, March 16, “Tenderly: The Rosemary Clooney Musical” presents a fresh, remarkably personal and poignant view of the woman whose unparalleled talent and unbridled personality made her a legend on film, recordings, radio, and TV. Showtime 8 pm. Located at 319 Duval St, Key West. Info and tickets at 305-296-9911; redbarntheatre.com.

The Studios of Key West
TSKW launches a brand new season with another extraordinary line-up of exhibitions, workshops, classes, open houses and more. Kick off the holidays from 9 am – 2 pm on Sat, Nov 24 at the Artisan Holiday Market, a festive indoor event featuring locally created gifts by over 20 artisans. On Fri, Dec 14 at 8 pm, Key West favorite, Larry Smith takes to the stage for a lively Holiday Concert that includes everything from classic jazz to Santa Claus set pieces. Be sure to check out their website for more upcoming events and a complete catalog and late-breaking updates. Located at 533 Eaton St., at the corner of Simonton in Key West. Info: 305-296-0458; tskw.org.

Tennessee Williams Theater
Key West: Go behind the music and inside story of Frankie Valli and The Four Seasons in “Jersey Boys – National Tour,” the Tony award-winning musical which plays for one night only on Mon, Nov 5 at 8 pm. On Fri, Jan 4 at 8 pm, it’s Broadway’s big fat hit, “Something Rotten National Tour” a combination of “The Producers + Spamalot + The Book of Mormon. Squared!” On Sun, Jan 20 and Mon, Jan 2, Key West’s favorite piano man, Bobby Nesbit, returns to the Tennessee Williams Cabaret Theater for his hit series, “Bobby In The Lobby.” Showtime: 8 pm. “Neil Berg’s 50 Years of Rock and Roll” takes to the stage at 8 pm on Fri, Feb 1 with the stars from Broadway’s greatest rock musicals, as well as other incredible rock ‘n’ roll singers. Located at 5901 College Rd., Stock Island/Key West. Info and tickets at 305-296-1520; keystix.com.

Waterfront Playhouse
Key West: The Waterfront Playhouse kicks off its 79th season on Nov 16 – 17 with “Carmen By Request! A Musical Journey” starring “Conch Diva,” Carmen Rodriquez followed by a catered post-performance cast party in the Sculpture Garden. On Tues, Dec 11 with the Tony Award-winning smash hit, “Peter and the Starcatcher,” the musical prequel to “Peter Pan” which plays through Sun, Jan 6. The critically acclaimed, Tony Best Play nominee, “A Doll’s House, Part 2” opens on Tues, Jan 22 and continues through Sat, Feb 9 followed on Tues, Feb 26 by the smash hit, “Young Frankenstein, The Musical,” the stage version of Mel Brooks’ iconic parody of the horror film genre. Plays through Sat, March 23. Located at 310 Wall St, Key West. Tickets and info: 305-294-5015; waterfrontplayhouse.org.

Other Florida Cities

January 12 – 13
Cape Coral Arts & Music Festival

Cape Coral: Now in its 34th 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 26 – 27 & February 1 – 3
33rd Annual Hoggetowne Medieval Faire

Gainesville: For two consecutive 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 Sat and Sun from 10am – 6pm and from 9:30am – 3pm on “Discount Friday,” Feb 1 when General Admission tickets are reduced. Find it at 3100 NE 39th Ave. in Gainesville. Info: HoggetowneFaire.com.

January 26 – 27
The Rolex 24

Daytona: More than 70 champion car racing legends from dozens of countries and all kinds of racing arenas flock to this annual 24-hour sports car endurance race that includes over 2,000 miles of high-speed action. There’s also various fan hospitality venues like the Champion’s Club, Rolex 24 Lounge and Taste of the 24 where you can enjoy live music and food samplings from twenty-Four of Daytona’s finest restaurants. Takes place at Daytona International Speedway, 1801 West International Speedway Boulevard, Daytona Beach, 1-800-PITSHOP.

1 – 3
ArtFest Ft. Myers

Fort Myers: ArtFest kicks off with a Friday Night Opening Party on Feb 1st and features many festival artists under the stars from 6 to 10 pm. 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. More info at ArtFestFortMyers.com