---

NORTH FLORIDA

---

JUANA GOOD TIME REGATTA

Navarre Beach 
Sept. 6-–8 

Each fall, hundreds of sailors gather on the beach at Juana’s Pagodas thatched-roof bar to compete on the water and party on the shore. Mariners from across the region and of all experience levels test their speed and skills captaining a variety of vessels including catamarans, trimarans, cruisers and sail-equipped canoes. The weekend kicks off with the Smooth Sailing party at Juana’s Pagodas, a popular beach volleyball bar near Pensacola Beach. The weekend’s lineup includes long-distance races, Hobie Wave races, buoy races and more. In addition to bragging rights, winners receive handmade trophies from Holley Hill Pottery and fresh flowers. After the last sail is lowered—as the event’s name suggests—good times await back on shore at both Juana’s Pagodas and Sailors’ Grill, where BBQ will be smoking and rum will be flowing. Live performances by Stevie Hall, Hippy Jim and the Jay Williams Band won’t disappoint. juanaspagodas.com

---

SING OUT LOUD FESTIVAL

St. Augustine
Sept. 6–29 

Music sensations Kacey Musgraves and St. Paul & The Broken Bones headline this month-long free music festival held at various locations. singoutloudfestival.com

---

DESTIN SEAFOOD FESTIVAL

Destin
Oct. 4–6 

Kick off Destin’s Fishing Rodeo with dishes from local restaurants, offerings from over 100 craft vendors or live music on one of the three main stages. destinseafoodfestival.com 

---

HARVEST FOOD AND WINE FESTIVAL

WaterColor
Oct. 24–26

A wine-lover’s dream with over 250 award-winning wines, star-lit dinners, celebrity winemakers and one of the largest beverage auctions in the country. dcwaf.org

---

FOO FOO FEST

Pensacola 
Oct. 31–Nov. 11 

The 12-day event includes art, music, dance and theater, with some of the South’s best talents like jazz band Big Bad Voodoo Daddy and art installation Fire and Rain, a sea of billowing holographic strands suspended above historic Intendencia Street. foofoofest.com

---

FLORIDA VS. GEORGIA GAME

Jacksonville
Nov. 2

Rally behind the Gators or the Dawgs (or simply revel in the spectacle of the day) at one of college football’s biggest match-ups, held at the TIAA Bank Field. flgajax.com

---

SEEING RED WINE FESTIVAL

Seaside 
Nov. 7–10

Sip and savor fine wine, cheese and other goodies at this annual event. In between tastings, shop local merchants such as the Seaside style and Ophelia Swimwear. seeingredwinefestival.com 

---

35TH ANNUAL FRANK BROWN INTERNATIONAL SONGWRITERS’ FESTIVAL

Gulf Coast of Florida and Alabama 
Nov. 7–17

This gathering of songwriters and musicians showcases the talents of artists like Sean Gasaway and Leslie Ellis. frankbrownsongwriters.com

---

WOLFSON CHILDREN’S HOSPITAL ARTS & ANTIQUES SHOW

Jacksonville 
Dec. 6–8 

The Paris-themed antiques showcase includes a fashion show with patients and benefits the neonatal intensive care unit. womensboardwolfsonchildrenshospital.com

---

CENTRAL FLORIDA

---

SHINE MURAL FESTIVAL

St. Petersburg 
Oct. 18–26 

From the growing collection of murals, like the Face of Twiggy painted by local artist Chad Mize, to the rainbow-painted intersection of Central Avenue and Fifth Street by Cecilia Lueza, St. Petersburg’s vibrant public art is fueling the city’s cultural explosion. This year’s internationally acclaimed event, hosted by the St. Petersburg Arts Alliance, will present 16 new public murals created by five international artists, four national artists and seven local artists. In addition to creative collaborations, SHINE has also partnered with several organizations such as NOAA, PangeaSeed Foundation, the LGBTQ Welcome Center and the local chapter of the Boys and Girls Club. The Arts Alliance hopes to promote a sense of unity and shared love of the arts by bringing to life vibrant large-scale images from the local community. Events include walking tours, art classes and educational talks aimed at celebrating street art and the beauty of diversity. shinemuralfest.com

---

CITY: FASHION+ARTS+CULTURE

Tampa
Sept. 14 

See the Tampa Museum of Art turned into a fashion runway. This year’s exhibition showcases the iconic designer Angel Sanchez and his timeless architectural dresses. tampamuseum.org

---

MOUNT DORA BICYCLE FESTIVAL

Mount Dora
Oct. 3–6

Bike across Central Florida at this premier cycling weekend event. Choose from one of 16 routes of varying difficulty, spanning three counties, and enjoy the scenery. mountdorabicyclefestival.com

---

FLORIDA BIRDING & NATURE FESTIVAL

Brandon 
Oct. 17–20 

Bring your binoculars and walking shoes. This festival offers scenic boat tours, keynotes, seminars from top field experts and several expeditions. floridabirdingandnaturefestival.org

---

AUTUMN ART FESTIVAL

Winter Park
Oct. 12–13 

Take a stroll down Winter Park’s charming Park Avenue and celebrate the harvest with more than 100 stalls featuring some of Florida’s best creators. winterpark.org

---

JOHN’S PASS SEAFOOD & MUSIC FESTIVAL

St. Petersburg 
Oct. 18–20

Bring your appetite to the East Coast’s second-largest seafood festival, with live music and a plethora of food stalls. johnspassseafoodfest.com

---

SARASOTA MOD

Sarasota
Nov. 8–10

Spend the weekend touring midcentury modern homes, attending talks and wandering galleries at the Sarasota Architectural Foundation–sponsored event. sarasotamod.com

---

ESCAPE TO MARGAVITAVILLE @ DR. PHILLIPS CENTER

Orlando 
Nov. 12–17

Put on your white sport coat and nibble on some sponge cake with Jimmy Buffett’s hit Broadway musical, set to the soundtrack of his most popular tunes. drphillipscenter.org

---

RENNINGER’S ANTIQUE EXTRAVAGANZA

Mount Dora
Nov. 15–17

This three-time-a-year event is back with almost 800 vendors from across the country. Find everything from assemblage artwork to comic books, rare furniture and handcrafted goods. renningers.net

---

SOUTH FLORIDA

---

ART BASEL: MIAMI BEACH

Miami Beach
Dec. 5–8 

Art Basel originated over forty years ago in the Swiss town of Basel as an art fair with more than 16,000 visitors and the aim of fostering artists’ careers. The Art Basel Miami that people know and love today launched in 2002 as an expansion of the Art Basel brand and has become one of the most important fairs in the world. Modern and contemporary artists representing more than 200 galleries gather at the Miami Beach Convention Center to exhibit paintings, digital art, sculptures, photography and more. But it’s not just the groundbreaking artwork that draws huge crowds. Elaborate parties unfold inside luxury hotels and upscale venues across the city, while celebrities from sports stars to Hollywood A-listers peruse the works and contribute to the festive atmosphere. Beyond the convention center, in artsy enclaves like Wynwood Art District and the Design District, a multitude of spinoff fairs, parties and experiences make up Miami Art Week. artbasel.com

---

TERESITA FERNÁNDEZ: ELEMENTAL 

Miami
Oct. 18–Feb. 9 

This exhibition at the Pérez Art Museum features Teresita Fernández’s sculpture Drawn Waters, a waterfall fashioned from a floor-to-ceiling sheet of steel covered in graphite, as well as other works. pamm.org

---

NAPLES STONE CRAB FESTIVAL 

Naples 
Oct. 25–27

Celebrate the opening of stone crab season at this festival on the Naples historic waterfront. Hop on a water taxi from the Old Waterfront to Tin City and witness the official cracking of the first stone crab. paradisecoast.com

---

FORT LAUDERDALE INTERNATIONAL
BOAT SHOW

Fort Lauderdale
Oct. 30–Nov. 3 

Wander among 1,500 vessels from sportfishing boats to skiffs to yachts and superyachts at the 60th annual show, where the industry’s best boat- builders will be on hand. flibs.com

---

KEY WEST RUNNING FESTIVAL / SOUTHERNMOST MARATHON

Key West
Oct. 12 

Competitors choose between full marathon, half-marathon or 5K routes going from Key West to Stock Island and back again. And yes, there’s an after-party. somomarathon.com

---

SEED FOOD AND WINE FESTIVAL

Miami
Nov. 7–10

Plant-based chefs like Marco Borges, Jules Aron and Colleen Holland host panels and cooking demos during this vegan weekend. seedfoodandwine.com

---

SIESTA KEY CRYSTAL CLASSIC

Siesta Key 
Nov. 15–18 

The beach transforms into an outdoor art gallery as dozens of sand sculptures take shape. Competitors build masterpieces like giant elephants and castles. siestakeycrystalclassic.com

---

CHRIS EVERT PRO-CELEBRITY
TENNIS CLASSIC

Delray Beach/Boca Raton 
Nov. 22–24 

The six-time U.S. Open title winner hosts this pro-celebrity event to raise money for her ongoing campaign against drug abuse and child neglect.  chrisevert.org

---

PARADISE COAST WINE & FOOD EXPERIENCE

Naples
Nov. 23 

Festivalgoers attend cooking demos, seminars and celebrity chef meet and greets, while enjoying great food and wine and event headliner Martha Stewart. paradisecoast.com

---