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NORTH FLORIDA

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30A WINE FESTIVAL

Alys Beach
Feb. 19–23

Satisfy your gourmet cravings with fine wine and fare at this annual jubilee, set in the heart of an idyllic coastal enclave. Chef Drew Dzejak of Caliza Restaurant kicks off the five-day fete with a four-course meal with wine pairings. Next fortify your inner Southerner at Friday’s popular B3 event with barbecue, beer and bourbon from vendors from around the nation, including Central BBQ and Reservoir Distillery. Learn the fundamentals of making the perfect cocktail at a toasty mixology seminar. The festivities continue on Saturday when revelers gather on the beautiful South Charles Street to enter the Grand Tasting, a culinary celebration with more than 80 wines from vineyards across the globe. Boozy brunch and a friendly game of croquet round out the weekend—croquet whites are encouraged. Guests also have a chance to win a basket of goodies in 30A’s annual silent auction, in which all proceeds support Children’s Volunteer Health Network. 30awinefestival.com 

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DICKENS ON CENTRE

Amelia Island
Dec. 13–15

Roam the streets of this Victorian inspired holiday festivity filled with costumed characters, live performances and vendors with seasonal gifts. Expect readings of ’Twas the Night Before Christmas as you sip hot cocoa and await the arrival of Saint Nick. ameliaisland.com

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2020 TOUR DE FELASCO

Alachua 
Jan. 11

Join fellow cyclists on 50 miles of trails that wind through rolling hills and creek crossings at the San Felasco Hammock Preserve State Park. This test of endurance raises money for the conservation of the park and the wildlife that reside there. sanfelasco.org

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30A SONGWRITERS FESTIVAL

South Walton 
Jan. 17–20

Take in four days of unmatched talent from some of the best writers and musicians making music today. More than 175 songwriters perform in venues from listening rooms to amphitheaters along 30A, a highway that bisects one of Florida’s most idyllic Gulf Coast settings. 30asongwritersfestival.com

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SAINT AUGUSTINE FILM FESTIVAL

St. Augustine 
Jan. 16–19

Mingle and party with filmmakers and enthusiasts at the 10th-annual celebration. Original films shown in five different screening rooms around downtown. staugfilmfest.com

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BUTTS & CLUCKS COOK-OFF ON THE BAY

Apalachicola Bay
Jan. 23–25

Win bragging rights and up to $15,000 in this grilling face-off with four categories: chicken, ribs, pork butt and brisket. Compete for the best deviled eggs or barbecue sauce. apalachicolabay.org

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OLUSTEE FESTIVAL

Olustee
Feb. 14–16

Spend the weekend at an arts and crafts show with makers and food trucks from across the country, then mosey over to Olustee Battlefield Historic State Park for a reenactment of Florida’s largest Civil War battle. olusteefestival.com

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STEINHATCHEE FIDDLER CRAB FESTIVAL

Steinhatchee
Feb. 14–16

Cheer on the crabs, fish the tournament and enter the raffles. Grab a bite and a sip in the food and wine garden before catching a parade and Rolling Stones and Garth Brooks tribute bands. steinhatcheechamber.com

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CENTRAL FLORIDA

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SURFING SANTAS

Cocoa Beach
Dec. 24 

Each year, Santa Claus kicks off Christmas Eve by trading in his sleigh for a surfboard. Now in its 11th year, Surfing Santas has become a holiday staple for the Space Coast. Hundreds of beard-clad surfers take to the waves in their best Christmas getups, often before a crowd of more than 10,000 onlookers. Every year the Santa wave swells, and organizers hope to see more than 1,000 Kris Kringles ripping this Christmas Eve, says founder George Trosset. The holiday craze does more than cause a scene—it has also raised more than $100,000 for charity. While the event is free, funds from T-shirt sales go to Grind for Life, an organization supporting families affected by cancer, and the Florida Surf Museum, which preserves the state’s surfing history. Surfing experience isn’t required to participate, but for those who’d like to avoid a wipeout, there’s plenty of fun on shore. Shredding begins at 8 a.m., and BYOB (Bring Your Own Beard) to compete in the costume contest. SurfingSantas.org

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ENCHANT CHRISTMAS

St. Petersburg 
Nov. 22–Dec. 29

Follow the elf on his search for Santa’s reindeer through this maze of lights and ice-skating trails. Ward off the cold and snowfall with a cup of hot cocoa from the Christmas Market, with more than 40 vendors.
stpete.enchantchristmas.com

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FLORIDA MANATEE FESTIVAL

Crystal River
Jan. 18–19

Enjoy live music, food trucks and fine art while celebrating one of Florida’s most iconic residents. Catch a ride to Three Sisters Spring to see manatees in their natural habitat. gomanateefest.com

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KUMQUAT FESTIVAL

Dade City
Jan. 25

Find the magic of Old Florida at the kumquat capital of the world. After visiting the car and truck show and the fresh farmers market, sample kumquat-inspired dishes like pie, ice cream, cookies, salsa and more. dadecitychamber.org 

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ROLEX 24 AT DAYTONA

Daytona Beach
Jan. 25–26

For 24 hours straight, race car drivers test their endurance on the Daytona International Speedway and compete in teams for the chance to win a Rolex Cosmograph Daytona watch. Fans can collect autographs, and access the University of Northwestern Ohio Fanzone. daytonainternationalspeedway.com

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FLORIDA FOOD AND BREWS FESTIVAL

Pinellas Park
Feb. 1

Test your taste buds and vote in the five categories of competition, including best vegan entree and best food truck. Catch music and games while supporting anti-violence and youth programs by sipping locally brewed beer or wine. foodbrewsfestival.com

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LAKERIDGE WINERY WINEFEST

Clermont
Feb. 7–9

Take a free wine tour with a glass of pinot in hand at this event highlighting the best of Florida wines. Listen to live music and browse aisles of local fine art. Don’t miss the return of the popular wine and cheese bar. lakeridgewinery.com

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WILD, WONDERFUL WITHLACOOCHEE

Lake Panasoffkee
Feb. 13–18

Paddle through the Withlacoochee River on a six-day kayaking adventure. Hearty meals keep paddlers energized en route from Lake Panasoffkee to the Gulf of Mexico.
paddleflorida.org

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SOUTH FLORIDA

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SUPER BOWL LIVE

Miami
Jan. 25–Feb. 1

Only 65,000 fans of the 2020 Super Bowl will watch history in the making from inside Hard Rock Stadium. As for the other 1.5 million football revelers expected to wash over downtown, a Miami-style party will be going off all week long. This free event invites fans to celebrate their favorite teams or just simply live it up with free concerts, local food, fireworks and 14 blocks of activities. Interactive technology and building projections keep the thrill of the game hyped up all week, and a players and legends meetup creates a unique experience for football buffs unmatched by other NFL events. To amplify the Miami Super Bowl Host Committee’s Ocean to Everglades conservation campaign, the Florida Fish and Wildlife Conservation Commission and the Everglades Foundation will have a presence at the Environmental Village, where attendees can learn about plastic pollution and also get up close and personal with Florida wildlife. This weeklong celebration unfolds on the waterfront grounds of Bayfront Park in the heart of Miami. miasbliv.com

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A MIRROR MAZE: NUMBERS IN NATURE

Miami
Oct. 12–April 12

The interactive mirror maze provides a hands-on experience that exposes mathematical patterns in the natural world. Puzzles and activities challenge guests’ critical thinking skills.
frostscience.org

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MIAMI ART WEEK

Miami
Dec. 3–8

A collection of shows, anchored by Art Basel, with attendance by artists from over 1,200 global galleries. Collectors, curators, museum professionals, enthusiasts and party people convene for a grand exhibition. artmiami.com

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PALM BEACH FOOD & WINE FESTIVAL

Palm Beach
Dec. 12–15

Dig in to some of the best food South Florida has to offer. Attend seminars hosted by prominent chefs including Clay Conley of Buccan and Lindsay Autry of The Regional Kitchen & Public House. pbfoodwinefest.com 

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PIGGY’S REVENGE OFF ROAD CHALLENGE

Venice
Jan. 5

This competition takes cyclists through a 10-, 20-, 40- or 60-mile stretch of Florida wilderness. Throughout the trails, expect to see alligators, snakes, deer and wild boar. Registration includes a ticket to compete, a Piggy’s Revenge T-shirt and a bratwurst fresh off the grill.
blog.piggysrevenge.com

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PALM BEACH MODERN + CONTEMPORARY

West Palm Beach
Jan. 9–12

The quieter cousin to Miami Art Week, this four-day event showcases pieces from the world’s top galleries, attracting seasoned art connoisseurs, collectors, budding enthusiasts and a posh Palm Beach crowd. artpbfair.com

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MIAMI INTERNATIONAL BOAT SHOW

Miami 
Feb. 13–17

Enhance your boating skills and keep up to date on the latest and greatest in fishing and cruising vessels. Join sailing seminars on the water or take a walk through the display room to satisfy all your boating and fishing needs. miamiboatshow.com

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WINTER STAR PARTY

Big Pine Key
Feb. 17–23

During the week of a new moon, astronomers from around the country gather in Big Pine Key to observe 360-degree views of clear skies and twinkling stars. Guests participate in photo contests, listen to prominent speakers and exchange information with fellow astronomy enthusiasts. scas.org