Your 4-Day Harvest Wine & Food Festival Itinerary
Words by Ashley Locke
Photos provided by DCWAF
If you’re going to book a fall getaway, make it one that tastes good and does good.
Every October, along the sugar-white beaches of Florida’s Scenic Highway 30A, the Harvest Wine & Food Festival transforms the town of WaterColor into a celebration of fine wine, elevated food, and real impact.
Hosted by the Destin Charity Wine Auction Foundation (DCWAF), this four-day festival is so much more than a wine weekend. It’s a way to unwind with intention. A chance to sip world-class wines while giving back to the next generation—helping provide everything from housing and mental health support to food and dental care for thousands of children in Northwest Florida.
Over the last two decades, DCWAF has donated more than $38 million to charities serving more than 100,000 kids, and every ticket sold helps keep that going.
Whether you’re clinking glasses at a winemaker dinner, dancing under the lights at Cerulean Park, or enjoying brunch at The Citizen with your besties, your weekend becomes part of a story much bigger than you.
So if your dream vacation includes coastal air, bold pours, good people, and an even better purpose, this is your sign. We’ve built the perfect itinerary to help you get the most out of Harvest Wine & Food Festival, both on and off the tasting lawn. Let’s make your weekend unforgettable and impactful.
Thursday: Winemaker Dinners + Sunset Strolls
What to do:
Arrive early and check into your beach cottage, then ease into the weekend with a bike ride down scenic 30A. Take the long way through WaterColor and grab a bite at The Perfect Pig or Fish Out of Water.
Where to be:
That evening, you’ll head to one of the Celebrity Winemaker Dinners—intimate, unforgettable meals hosted in private homes and restaurants across South Walton. Each one features premium wine pairings and dishes created by renowned chefs. Whether you’re team steakhouse (hi, Seagar’s) or team coastal chic (see: Ambrosia), you’re in for something special.
Don’t miss:
Sneak in a sunset walk on the beach before dinner. Golden hour hits different here.
Friday: Wine After Dark
What to do:
Start your morning with a little Vitamin Sea. Take a coffee and croissant to go and enjoy it on the beach. Then, browse the shops at Grand Boulevard or rent a paddleboard for a quick dip in Western Lake.
Where to be:
When the sun goes down, Harvest After Dark lights up Cerulean Park. Think upscale picnic-meets-garden party, with a side of swagger. Expect exciting flavor pairings, bold pours from celebrated vintners, and curated bites from some of the Southeast’s most talented chefs.
Pro tip:
Wear something fabulous—but comfortable. There will be bubbles. There will be dancing.
Saturday: Grand Tasting, Great Cause
What to do:
Clear your calendar from 1–4PM because the Grand Tasting is calling. Set in the heart of WaterColor’s Cerulean Park, this marquee event is the moment: dozens of world-class wineries, a who’s-who of regional chefs, and all the bites and pours you can dream of.
Want to level up?
Spring for a VIP ticket. You’ll score access to the elevated tent experience (hello, lounge seating, live music, and exclusive cocktail bars).
More to love:
Snap photos under the oak trees, listen to live music in the beer garden, and don’t skip the barbecue stations. Trust us.
Sunday: Brunch, Beach, Repeat
What to do:
Not ready to say goodbye? Good. Sunday’s festival brunch is the final sparkle on your wine-soaked weekend. A Taste of Italy Cocktail Brunch features Italian-inspired dishes and clever cocktails served at a stunning private residence.
After brunch:
Take one last beach walk, stop for oysters and rosé at Bud & Alley’s, and toast to the good you’ve done this weekend.
Can’t Be There in Person?
Join in from wherever you are by participating in the Virtual Auction, where every bid goes toward helping kids—and enters you for the chance to win an in-home chef experience for eight.
Harvest Wine & Food Festival is a gathering of good-hearted people who believe in savoring life—and making it better for someone else while they do. Book the cottage. Bring your people. Do some good. And make sure to grab your tickets before they’re gone.
