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.
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.
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.
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.
September 1 – November 30
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.
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.
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.
November 7 – 9
Cheeca Lodge & Spa All American Backcountry Fishing Tournament
Islamorada: War heroes and world-class anglers compete for trophies and awards during Cheeca Lodge’s 6th annual catch and release competition. This first-class tournament kick-offs on Thur, Nov 7 with a cocktail reception, rules meeting, patriotic banquet on the beach and auction. Tickets to attend the kickoff dinner and auction are available to the community with advance reservations. Info: 305-712-7166; cheeca.com.
Key West: Known principally as the vocalist, lead guitarist and composer for the Moody Blues, Justin Hayward is an enduring talent that has helped to define the times in which he worked. Doors open 7pm; Showtime: 8pm. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
MaarVelous Pet Rescues
“Spay-ghetti & No Balls Holiday Gala”
Key Largo: This fun annual dinner, auction and mega dance party benefits MarrVelous Pet Rescues which is dedicated to uniting pets with loving homes and families. Takes place at 6:30pm on the waterfront at the beautiful Snook’s Bayside Restaurant & Grand Tiki, MM 99.9 Bayside, Key Largo. Tickets are EXTREMELY limited and not sold at the door. Info and tickets: 305-453-1315; spayghetti.com.
Thunder From Down Under
Key West: For 15 years, Australia’s hottest export has been “eye candy” for women of all ages with the dancers making women happy in the blink of an eye and the unbuttoning of a shirt! This show is the ultimate bachelorette party experience. Showtimes: 7pm and 10pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
Mote Marine Laboratory’s Ocean Fest: A Community Celebration
Islamorada: Underwater and outdoor enthusiasts, eco travelers and families celebrate the marine environment at this fun Upper Keys festival that includes crafts, games, music, food, shopping and a great silent auction. Takes place from 11am – 5pm at Founders Park, 8700 Overseas Hwy (MM 87 Bayside). Info: 941-356-0964; mote.org.
22nd Annual Taste of The Islands
Marathon: This award-winning event draws several thousand attendees and features local restaurants, live entertainment, vendors and artists, a tribute to veterans, fashion show, kids activities plus live and Chinese auctions. Takes place from 11am – 5pm at Marathon Community Park, MM 49, oceanside, Marathon. Info: 305-923-9976.
Who’s Bad: The Ultimate Michael Jackson Experience
Key West: This power-packed performance of Michael Jackson’s expansive catalog has ignited crowds on every continent and can only be described as a jaw-dropping, musical must-see. Doors open 7pm; Showtime: 8pm. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
The Wizards of Winter
Key West: This family-friendly Holiday Rock Event features the former members of the Trans-Siberian Orchestra, Rainbow, Blue Oyster Cult, Ted Nugent, The Irish Tenors and more. Join them on a musical journey inside a snow globe in search of the true meaning of Christmas. Doors open 7pm; Showtime: 8pm. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
Old Island Restoration Foundation’s 60th Anniversary Kick-Off Party
Key West: This special event celebrates Key West’s architecture, culture and history with Historic Home Tour Posters, exhibits, the ceremonial return of an original Captain Francis Watlington painting, wine tasting, small bites and more. Takes place from 5 – 7pm in Lily’s Garden at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
A Night At The Museum: Bootlegger Bash
Islamorada: This signature fundraiser for the Keys History & Discovery Museum is one of the Upper Keys most fun annual events. The clandestine evening features live jazz, booze, and gaming – a roaring good time! Takes place from 6 – 11pm at the Keys History & Discovery Center, MM 82 on the property of the islander Resort in Islamorada. Info and tickets: 305-922-2237; keysdiscovery.com.
2nd Annual Florida Bay Music Festival
Islamorada: Southern rock legends 38 Special and country star Chris Janson highlight this special fundraiser for Casting for Cats, Big Dog Rescue Ranch and Mangrove Mike’s Everglades Education. Gates open at 3pm; Music at 5pm. Takes place at Founders Park, MM 87 in Islamorada. Tickets and info: 305-664-2012; castingforcats.org.
November 20 – 24
Key West Film Festival
Key West: This annual event showcases films that exhibit excellence in storytelling and features screenings and special events at landmark venues throughout Key West, including the San Carlos Institute, Studios of Key West and Key West Theater. Info: kwfilmfest.com.
38th Annual Key Largo Chamber Of Commerce Cook Off
Key Largo: This legendary culinary competition challenges both professional and amateur cooks and chefs, as well as young aspiring chefs, to create their very best soups and chowders, appetizers, main dishes, sides and salads, as well as desserts. Takes place from 6 – 8:30pm at the Holiday Inn, MM100, Oceanside in Key Largo. Tickets: Key Largo Chamber of Commerce. Info: 305-451-4747; keylargochamber.org.
Old Fashioned High Tea in Lily’s Garden
Key West: Enjoy a relaxing afternoon tea in the beautiful Garden at Key West’s Oldest House. The menu includes a fresh pot of tea, petite fresh currant & chocolate scones, a selection of tea sandwiches and chef’s selection of desserts. There will also be a special guest speaker on hand to talk about the history of Emiline Wattlington. Takes place from 1 – 3pm in Lily’s Garden at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
Max Weinberg’s Jukebox
Key West: Max and his 4-piece band are live on stage, performing over 200 rock & roll classics, chosen in real time as the audience calls out their favorties from a video menu. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
The Architecture of Key West – Garden Lecture Series
Key West: Did you know that Key West is the largest historical district of wooden structures on the US Department of the Interior’s National Register of Historic Places? Join art historian, Snow Philip, for a fascinating presentation about the wide variety of styles and influences that led to Key West’s unique architectural fusion. Gates open at 6pm in Lily’s Garden at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
Lighting of the Bight: Key West Harbor Walk of Lights
Key West: The Key West Harbor lights up the waterfront with a fresh pine Nautical Christmas Tree, a Fishing Buoy Tree and the original Key West Lobster Trap Tree. This “Harbor Walk of Lights” stays lit nightly through New Year’s Eve and stretches along the Key West Historic Seaport and Key West Bight Marina.
Holiday Artisan Fair
Key West: Enjoy cookies and coffee as you stroll through a friendly, festive indoor market. Each year, over 20 artisans present unique and locally produced gifts: jewelry, textiles, home accessories and quality crafts. Takes place from 9am – 2pm at The Studios Of Key West, 533 Eaton St, Key West. Info: 305-296-0458; tskw.org.
Big Pine & The Lower Keys Island Art Festival
Big Pine: This fun annual holiday event always draws a big crowd and includes live music, exhibits, arts and crafts, food vendors and more. Free admission. Takes place from 8am – 2pm at the Lower Keys Chamber of Commerce, MM 31, oceanside. Info: 305-872-2411; lowerkeyschamber.com.
December 1 – 31
Key West Holiday Fest
Key West: Key West’s colorful month-long holiday celebration includes all kinds of fun festivities that takes place all over the island. From the lighting of the Harbor Walk of Lights at the historic Key West Bight, holiday parades and tours of historic homes and decorated inns to tree lighting parties, art shows and outrageous New Year’s Eve celebrations, it’s one hoot of a good time. For a complete list of events go to keywestholidayfest.com.
Tree Trimming Party & Toys For Tots Drive
Key West: Bring your own nautical ornament for Schooner Wharf Bar’s big beautiful 8’ Christmas Tree and enjoy a free holiday cocktail — rum egg nog, Swedish glog or hot applejack. Prizes for most original, most nautical and most popular with the crowd. Takes place at 5pm at the Schooner Wharf Bar, in Key West’s Historic Seaport. Info: 305-292-3773; schoonerwharf.com.
I Love Stock Island Holiday Lighting Ceremony
Key West: Stock Island kicks off the season with a festive holiday tree lighting ceremony and Welcome reception. Takes place from 5:30 – 6:30pm at Fishbusterz parking lot at the corner of Maloney and 4th Street. Info: ILoveStockIsland.org.
Lighted Bike Ride
Key West: Festively decorated bikes parade through Key West. Ride begins at Bayview Park at 7pm. Registration at 5pm and only requires an unwrapped gift for the Holiday Helpers Toy Drive. Info: wesleyhouse.org.
Rumours: A Fleetwood Mac Tribute
Key West: This highly acclaimed Tribute Band recreates the signature harmonies of the legendary Fleetwood Mac. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
15th Annual Florida Keys Holiday Festival
Islamorada: A 35’ holiday tree blows magical snow at this festive extravaganza which includes a parade, caroling, holiday gift bazaar, delicious food, Vino Village, live music and a silent auction of masterpiece ornaments created by local artists. Takes place from 4 – 10pm at Founders Park, MM 87, Bayside. Info: 305-664-4503; islamoradachamber.com.
Lighted Bike Ride
Marathon: Festively decorated bikes parade through Marathon. Ride begins at the Frontage Road of the Marathon Airport at 7pm. Registration at 6:30 pm and only requires an unwrapped gift for the Holiday Helpers Toy Drive. Info: wesleyhouse.org.
December 6 & 13
Holiday Historic Inn Tours
Key West: Enjoy two enchanted self-guided tours of five different decorated inns and a sampling of holiday treats and cheer at each property. Takes place on two consecutive Fridays. Info and tickets: 305-296-4959; keywestholidayfest.com.
Key West: Renowned for her clever, observational humor and spontaneous wit, Paula Poundstone will keep you laughing all the way home. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
10th Annual Light Up Key Largo!
Key Largo: For one magical night, you can ice skate in the “Diving Capital Of The World” as Key Largo lights Monroe County’s tallest Christmas tree. This family friendly celebration also includes an Ice Skating Rink, Santa’s Workshop, Carolers lots of holiday goodies and lots more. Tree Lighting at 8pm. Takes place from 5 – 9pm at the Murray Nelson Government Center, MM 102. Info: 305-451-1414; keylargochamber.org
2nd Annual Lighting of the Light House & Boat Parade
Marathon: Enjoy food, music, performances, holiday shopping, Santa Claus and Marathon’s annual Holiday Boat Parade all centered around the lighting of the iconic lighthouse at Faro Blanco Resort & Yacht Club, 1996 Overseas Hwy. Takes place from 4 – 9pm. Boat parade sets sail at 7pm.
Key Colony Lighted Boat Parade
Key Colony Beach: Key Colony’s Lighted Boat Parade shoves off at around 6pm from the 7th Street Canal and makes three passes at the Judges Stand before heading up and down the 8th – 12th Street canals. Best viewing is from the Sadowski Causeway and just behind City Hall. Info: 305-743-7214.
Eaton Street Christmas Stroll
Key West: The Studios Of Key West, Key West Theater, St Paul’s Episcopal Church, Tropic Cinema and the Key West United Methodist Church come together to produce this new holiday tradition on Eaton Street. Enjoy a short Christmas-themed presentation with caroling as you stroll from stop to stop. Takes place at 5pm. For tickets go to tskw.org.
A Peter White Christmas
Key West: Peter White’s special holiday concert brings together Euge Groove, Vincent Ingala and Lindsey Webster for a fun night of smooth jazz. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
December 13 – 15
“I Love Stock Island” Festival
Key West: Celebrate Stock Island’s culture and heritage with three great days of the very best Stock Island has to offer including music, foodie events, wine, beer & rum pairings, history & art studio tours, water sports and fresh straight off the boat seafood! Takes place on Stock Island. Info: 573-680-5468; ilovestockisland.org.
Stock Island Lighted Boat Parade
Key West: Vessels of all shapes and sizes – from tri-masted schooners to dinghies to local Shrimp boats light up the night and compete for great cash and prizes. Parade starts at 7pm, but come early for great happy hour food at Matt’s & the Salty Oyster as well as concession multiple bars and spectacular decorated boats. Free viewing events at Stock Island Marina Village and Safe Harbor with live music at Hog Fish Bar & Grill at the official after party.
12th Annual Gingerbread House Making Party
Key West: Get your gingerbread on during this free, hands-on event that takes cookie making to a whole new level. Takes place from 11am – 3pm in Lily’s Garden at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
29th Annual Schooner Wharf Bar Lighted Boat Parade
Key West: A magical nautical display of lights and creativity are the hallmark of this favorite holiday maritime event which takes place in the Key West’s Historic Seaport. The boats come very close to the docks of the Schooner Wharf Bar where the Judges Stand is located which makes it a great vantage point. Festivities kick off at 6pm. Parade starts at 8pm followed by a big Awards Party. Info:305-292-3773; schoonerwharf.com.
6th Annual Parade Of Paws & Holiday Bazaar
Key West: Bring your dogs, wear a t-shirt with a pix of your pet or walk with a paddle displaying your pet’s photo during this unique event that helps support the Florida Keys SPCA. The Bazaar features entertainment, food vendors, a Kissing Booth, holiday gifts and more! Takes place from 10am – 2pm at Higgs Beach. Info: 305-294-4857; fkspca.org.
Key Largo Lighted Boat Parade
Key Largo: The waters of Blackwater Sound in Key Largo shimmer as decorated boats parade along the shoreline in celebration of the holiday season. Top spots for viewing and libations traditionally include Sundowners, Señor Frijoles and the Marriott Key Largo Bay Resort, located between MM 103-104. Info: 305-451-4502.
Key West: Front man for the legendary rock band, Poison, chartbuster Bret Michaels gives an explosive performance you won’t soon forget. Doors open 7pm; Showtime: 8pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
Noche Buena – Christmas Eve Feast
Key West: Why go to a restaurant on Christmas Eve when you can enjoy a real Key West family dinner? “Noche Buena” is a long celebrated tradition in latin communities and is proudly celebrated in Key West by local families. Local resident Wayne Garcia and his family will be serving up a traditional menu of Roast Pork, Black Beans and Rice, Plantains and postre. Takes place from 6 – 10pm in Lily’s Garden at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
December 27 – 28
60th 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. This year the tour includes a Bonus 6th Stop at historic inns/hotels that will feature free drinks and nibbles.The tours take place from 3 – 6pm 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.
“1860’s or 1960’s” Costume Gala
Key West: Celebrate New Year’s Eve in a ‘60s-time warp. Travel back to Jackie O, the Hippies, or even those adorable Madmen at Key West’s most exclusive costume-dinner party. Includes a lively Cocktail Hour, Sit-Down Dinner, Open Bar, Champagne Toasts, Music and Midnight Countdown. Reserve early – this is always a sell-out. Gates open at 6pm with dinner at 8:15pm in Lily’s Garden at the Oldest House Museum, 322 Duval St. Info: 305-294-9501; oirf.org.
New Year’s Eve Celebrations
Florida Keys & Key West: Raucous New Year’s Eve celebrations take place from Key West to Key Largo and include the lowering of a Pirate Wench from the mast of a tall ship at Schooner Wharf Bar in Key West (305-292-9520); the descent of Key West’s world-famous drag queen, Sushi, in a 6’ red high heel from the top of Key West’s Bourbon Street Pub Complex at 730 Duval Street (305-294-4737); and a spectacular fireworks extravaganza over Blackwater Sound between MM 103-104 in Key Largo (305-853-1685).
Key West Dachshund Walk
Key West: Frost free Key West becomes a “wiener wonderland” when about 200 dachshunds and their owners take a New Year’s Eve stroll through the island’s picturesque downtown. The “Weiner Walk” begins at noon at the corner of Whitehead and Fleming streets. The route, deliberately kept brief in deference to the dogs’ short legs, encompasses the 400 block of Fleming St, 500 block of legendary Duval St and one-block length of Appelrouth Lane. Info: email@example.com.
Songwriter Speakeasy Series: Eric Paul Levy, Raven Cooper, Michael McCloud
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.
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 11 – 12
16th Annual Big Pine & Lower Keys Nautical Expo
Big Pine: Get great deals on all things nautical as well as on local arts and crafts, clothing and jewelry. Live music, food and beverages, too. Free admission and parking. Takes place from 8am – 2pm on the grounds of the Lower Keys Chamber, MM31, Oceanside. Info: 305-872-2411; lowerkeyschamber.com.
January 11 – 12
7th Annual Florida Keys Celtic Festival
Marathon: Break out your kilts and dancing shoes because this festive Gaelic celebration
will have you kicking up your heels. Enjoy top acts by international Celtic bands, Celtic vendors, Celtic food and beer, highland athletics, and a children’s glen. Festival begins on Sat, Jan 11 from, 10am – 7pm and continues on Sun, Jan 12 from 11am – 5pm at Marathon Community Park, MM 49. Tickets and info: 941-625-8544; keystix.com.
Key West: Ranked by Comedy Central as one of the “100 Greatest Standups of all Time,” actor and comedian Sinbad will have you rolling in the aisles. Showtime: 6:30pm. Must be 21+. Takes place at Key West Theater, 512 Eaton St. Info: 305-985-0433; thekeywesttheater.com.
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.
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.
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.
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.
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.
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.
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.
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; firstname.lastname@example.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.