For most of the country, fall is for light sweaters, apple picking, pumpkin patches, and copper-colored leaves. In South Florida, it’s all about less humidity, stone crabs, and the occasional cold front (read: a low-70s breeze). While our definition of “fall” might not be a traditional one, it’s still a beautiful time to be on Florida’s Paradise Coast. Throughout the season, on Marco Island and in its surrounding areas (from Naples and the Everglades, northwest to Immokalee), you can go to a stone crab or film festival, meet Martha Stewart, run a Thanksgiving 5K, and see what it’s like to celebrate the Christmas season island-style. The best part: you won’t even need a jacket.
Saturday, October 12 Norris Community Center This Florida Gulf Coast-born band is back to rock out with their neighbors. Since forming in 1999, the Swinging Bridge Bluegrass Band has become a fixture in the Florida bluegrass scene. At this show, you can hear covers of classic bluegrass hits and favorites from the band’s first-ever album, Rough Edges, like “Corn Don’t Grow,” “Thanks a Lot,” and “Only Hell My Momma Ever Raised.” Cost: Tickets are $25 in advance, $28 at the door
October 17, November 21 Fleischmann Courtyard On the third Thursday of every month, head to Third Street South for a live concert with a rotating roster of local musicians. (FYI: more dates are added around Thanksgiving and throughout the holidays, too.) While Third Thursdays on Third makes a fun night out for the whole family, turn it into a date night with your S.O. at one of several restaurants and bars along this stretch downtown. Live music runs from 6-9pm, so grab dinner and drinks at The Continental or Campiello before or after the show. Pro tip: if you go to The Continental, get the Key Lime Blackberry Pie… and thank us later. Cost: Free
Saturday, October 19 Mercato Prost, Naples! Oktoberfest is upon us, and Naples doesn’t disappoint in the festivities department. Back for the eighth year in a row, Brew-Ha-Ha is a craft beer festival with 60-plus Florida breweries pouring -- this is not a drill -- unlimited beer samples. The more beer you drink, the more festive you’ll feel, so fill up your “bierstiefel” (your beer boot) and enter yourself in stein-holding and beer-gear costume contests. The festival runs from 5-9pm, with live music from Soulixer, raffles, cheese & beer pairings, and plenty of lederhosen to get you in the spirit. Cost: General admission tickets are $35, $40 at the door
November 15 The Ritz-Carlton Golf Club Here’s a golfer’s dream: getting to play nine-holes with a PGA champ. Lucky for you, Marriott Bonvoy is here to make that dream a reality -- and all you need is a few points to cash in. They’re offering an afternoon with pro Larry Ziegler and his son, world-class instructor Tony Zeigler, where the father-son duo will show you how to shave a few strokes off your score. Then, once you’ve sharpened your skills, you can challenge them out on the green. Marriott Bonvoy offers benefits and endless experiences at more than 7,000 hotels across the globe, so whether you’re into live music, exclusive dining events, or luxury VIP experiences, you’re bound to find a perk that fits your lifestyle. Of course, they’ve got you covered on where to stay after the afternoon, too. Cost: Starting bid at 70,000 points. Auction terms apply.
Monday, October 21-Wednesday, October 30 Various locations Fall is one of the best times to brush up on your cooking skills, seeing as the holidays are right around the corner. Naples Originals is a group of 25-plus local, independent restaurants, and for the fifth year in a row, they’re bringing their skills to the public. Naples Originals’ Foodie Camp hosts 10 days of cooking and mixology classes led by the head chefs, owners, and lead bartenders from Alexander's Restaurant, 7th Avenue Social, Ridgway Bar & Grill, and other favorites. As an added bonus, the money raised benefits culinary training programs at St. Matthews House and Naples Originals’ scholarships for Florida Gulf Coast University hospitality students. Cost: $60 per person, per class (includes demo, glass of wine, recipes, and raffle entry)
Thursday, October 24-Sunday, October 27 Various locations Now in its 11th year, the Naples International Film Festival brings together filmmakers and film aficionados from all over the world. Over four days, attendees can expect to screen 60-plus narrative, documentary, and short films; learn from filmmaker-led panel discussions, and even dress to impress at an opening night party, and later, an awards ceremony. Artis-Naples is hosting the festival, but various films will be shown at Silverspot Cinema, just 10 minutes away. Cost: Varies by event
Ongoing Marco Island Historical Museum Before there were rich snowbirds and retirees, Marco Island was home to the Calusa and Muspa Indian tribes and their pre-Columbian art. In 1896, the Smithsonian Institution sponsored an archeological expedition to Marco Island to see what Native Ameican artifacts they could find… one being the Key Marco Cat, which has been on display at the Smithsonian ever since. Standing six inches tall and carved from native hardwood, this cat is considered one of the finest pieces of Pre-Columbian Native American art ever discovered in North America. For 25 years, local historians have been fighting to get this famous cat (and other artifacts from that 1896 expedition) back in Marco Island, where they belong. Earlier this year, they succeeded, when the Key Marco Cat, a ceremonial mask, an alligator figurehead, a painted human figure, and a sea turtle figurehead went on display together, at home, for the first time in 100 years. Cost: Free
Friday, October 25-Sunday, October 27 Downtown Naples What South Florida lacks in fall leaves, it makes up for in stone crabs. Mid-October officially kicks off the season, and to celebrate, Naples throws an annual festival with stone crabs, live music, an ice cream eating contest, stone crabs, raffles, stone crabs, other seafood, boat rides, and 20-plus participating Florida restaurants with -- you guessed it -- stone crabs. You don’t want to miss the traditional “cracking of the first stone crab claw” by local leaders, which will kick-off the festivities at 5pm that Friday. It’s followed by a Bob Marley tribute concert at Tin City, which is always a good idea. Cost: Free admission (food, drink, and activities priced separately)
Saturday, October 26-Sunday, October 27 Big Cypress Gallery Celebrate fall like only Floridians can: with a swamp walk. Led by famed wilderness photographer Clyde Butcher and his wife, Niki, the walk begins at their Everglades-based Big Cypress Gallery, which sits in the middle of 14 acres of swamp land in Big Cypress National Preserve. Swamp walks will happen every hour, on the hour (from 9am-3pm), and all proceeds benefit the preserve’s education department. Cost: $50 per adult, free for children
Saturday, November 23 Cambier Park Back for a third year, the popular Paradise Coast Wine & Food Experience featuring Martha Stewart offers the best bites, wines, craft beers, and spirits from the surrounding area. It’s a day-long festival featuring local restaurants, chefs, and vendors, along with a Grand Tasting tent, cooking demonstrations, chef meet-and-greets, and seminars. The food and drinks are reason enough to go, but as an added bonus, you’ll have a chance to meet some of your favorite celebrities: like E! stars Brie and Nikki Bella, SOMM master sommelier Ian Cauble, and, drum roll please… Martha Stewart. Cost: Tickets start at $65 for adults (21+ only)
Thursday, November 28 Cambier Park Feel better about engaging in the age-old Thanksgiving tradition -- aka stuffing yourself with turkey and promptly passing out on the couch -- by running 3.5 miles beforehand. Gulf Coast Runners will host a 5K at Naples’ Cambier Park, which, in true running fashion, you’ll have to wake up early for (registration opens at 6am). In true Thanksgiving/food coma fashion, however, there WILL be pumpkin pie and apple cider afterward. Cost: $25 per adult
Friday, November 29-Monday, December 23 Naples Botanical Garden The 170-acre Naples Botanical Garden is already a sight to behold, and for 25 nights this November and December, it gets even more beautiful after dark. Like something out of a real-life fairytale (or a really trippy scene from Alice in Wonderland), the gardens will be illuminated with thousands of lights and play host to live music, a “wishing tree,” and performances by the Opera Naples Youth Chorus, Naples Ballet, and others. When you want something to eat or drink, stop by the garden’s own Fogg Café, serving specialty menu items and signature cocktails. Cost: Adult tickets starting at $12 for members/$25 for non-members
Wednesday, December 4 Off the Hook Naples He’s opened for big names like Joe Rogan, Pete Davidson, Michael Che, and Mike Epps, he beat out 180 other comics for the title of “Florida’s Funniest” in 2019, and he’s written for the MTV show Wild'N'Out. Oh, and he’s only 25. It’s safe to say you should probably see Cam Bertrand when he comes through Paradise Coast, before he’s (more of) a big deal and you can’t afford to anymore. Cost: Tickets start at $22
Monday, December 2-Sunday, December 15 Various locations Everyone loves a good dining deal, and Winter Sizzle SWFL Restaurant Week gives Paradise Coast locals just that. From Marco Island to Cape Coral and everywhere in between, guests can eat at 60-plus participating restaurants and get reduced-price, prix-fixe lunches (two courses) and dinners (three courses). To make you feel extra great about the bargain, $1 from every meal will benefit the Sizzle SWFL FGCU Food & Beverage Scholarship, which gives Southwest Florida-area high school graduates up to $10,000 in scholarship aid to attend the hospitality food & beverage program at Florida Gulf Coast University. Cost: Lunch starts at $16, dinner starts at $26
Friday, December 6 Fifth Avenue ’Tis the season to… sing and dance to Christmas tunes in the streets, as if that were a normal thing. During the annual Christmas Walk & Tree Lighting Ceremony, saunter down Naples’ famed Fifth Avenue and see holiday performances by lots of local choirs, bands, dancers and theater troupes. It all leads up to the official 2019 Christmas tree lighting, which will be done by Mayor Bill Barnett and ABC7 anchor, Krista Fogelsong. Cost: Free
Saturday, December 7 Veterans Park Celebrate Christmas like the (Marco) islanders do. To kick-off the holiday season, the city’s annual tree-lighting celebration invites all the locals to don their favorite Christmas garb, watch Christmas-themed dances, sing to Christmas music, and of course, see a 40-foot Christmas tree get lit. Merry Christmas, Marco Island! Cost: Free
Jennifer Agress is a South Florida-based food, travel, and lifestyle writer who loves being able to celebrate Christmas outdoors… in shorts. Follow her on Instagram at @jenniferagress.