On Saturday, November 21, 2026, the 13th Annual Boca Raton Wine & Food Festival takes over Sanborn Square Park in downtown Boca Raton, just south of Mizner Park. It’s an easy, worthwhile reason to turn a Saturday night into a full South Florida weekend — and Hollywood, FL makes a surprisingly smart home base for it.
A Grown-Up Night Out Just Up I-95
The all-inclusive festival runs General Admission from 7 to 10 p.m. (tickets start at $65), with earlier entry for VIP ticket holders. Expect fine dining from South Florida chefs across culinary villages — Italian, American, Mediterranean, Asia Pacific, Spanish, and Sweet Endings — plus unlimited craft beer, wine, and spirits, a Fine Wine & Artisanal Cheese Village, the 9th Annual Craft Brew Battle between local breweries, and live music all evening. It benefits the Children’s Giving Foundation, and it’s a 21-and-up event, so plan your ride accordingly. Organizers note VIP tiers tend to sell out.
Why Base Yourselves in Hollywood Instead of Boca
Boca Raton is roughly 40 minutes north of Hollywood on I-95, and plenty of festival-goers would rather stay south of the action than pay beachfront Boca rates for a single night out. Basing your trip in Hollywood keeps you close enough for an easy drive up for the festival (or a Brightline ride from the Fort Lauderdale station) while putting you minutes from Hollywood Beach, the Broadwalk, and Fort Lauderdale’s own restaurant scene for the rest of the weekend.
Built for Groups Who Don’t Want to Split Up
If the guest list crept past “the two of us” the way these food-and-wine weekends tend to, Total Oasis is the easy fix. The five-unit property sleeps up to 30 combined, so a group can split up for the festival, designate drivers, and regroup afterward without anyone sleeping on a couch or splitting across two separate rentals. It also means the crew heading to Boca and the crew that would rather watch the sunset from the Broadwalk can both get their night exactly the way they want it.
Plan the Rest of the Weekend
With the festival anchoring Saturday night, it’s easy to build out a full weekend: Friday on Hollywood Beach, Saturday afternoon by the pool before heading up to Boca, and Sunday brunch before everyone heads home. With more than 1,600 guest reviews across platforms, Kismet Getaways properties are a known quantity for groups who want a comfortable, low-drama base for exactly this kind of weekend.
Ready to lock in your weekend? Browse Total Oasis and the rest of the Kismet Getaways properties before the dates fill up.