There’s no better way to experience the Florida Keys than through its food. From fresh-caught seafood and island-inspired flavors to family-owned restaurants and creative chefs, the Upper Keys dining scene reflects the unique culture that makes this destination so special.

This October, that culinary spirit takes center stage as Taste the Keys returns for a month-long celebration of local flavor. Running October 1–31, the annual festival invites both visitors and locals to discover specially crafted prix-fixe menus at participating restaurants throughout the Upper Keys, offering an affordable way to sample some of the area’s best cuisine.

“Taste the Keys was created to replace the Key Largo Chamber’s Cook-Off event. We thought it was more important to increase traffic into the actual restaurants during the slower season,” says Suzi Youngberg, President & CEO of the Chamber. “We are thrilled with the participation over the last few years and look forward to growing Taste the Keys into a Keys-wide event!”

Each restaurant creates exclusive lunch, dinner, or all-day menus that showcase signature dishes and seasonal specialties. The prix-fixe format gives diners a chance to sample more of what a restaurant has to offer. It’s the perfect excuse to revisit a longtime favorite, try something you’ve always been curious about, or discover a new spot altogether.

For participating restaurants, the timing is especially meaningful. October traditionally brings a slower pace to the Upper Keys, making Taste the Keys an opportunity to draw both locals and visitors through the doors, help diners discover new favorites, and keep more dining dollars circulating within the community.

Adding a little friendly competition to the festivities is the Signature Dish Showdown, where participating restaurants nominate one standout item from their menus to compete for the title of Best Dish in the Upper Keys. Diners become the judges, tasting their way through the month and casting votes online for their favorites. The competition was tight in 2025, with Sundowners ultimately taking the title for its Key Lime Seafood dish. With even more creative contenders expected this year, the race for Best Dish could be even closer.

For food lovers looking for a guided adventure, the Taste the Keys Trolley Foodie Tours offer an unforgettable evening on the town. Guests climb aboard the trolley and travel between featured restaurants, enjoying curated tasting menus and drink pairings at each stop. Rather than settling in at just one restaurant, guests can experience several culinary destinations in a single evening—without having to plan the route or worry about parking.

Forget bar hopping. This is bite hopping, Keys style!

The trolley tours turn dinner into an experience all its own, bringing together great food, local hospitality, and the fun of sharing the evening with fellow food lovers. Each stop offers something different, giving guests a taste of the variety and personality that define the Upper Keys dining scene. It’s a fun night out for everyone—from couples looking for a memorable date night to groups of friends ready to eat their way through the Upper Keys.

From inventive flavors to waterfront favorites, Taste the Keys celebrates everything that makes dining in the Upper Keys unique. Whether you’re hunting for the next award-winning dish, enjoying a progressive dinner aboard the trolley, or simply savoring a great meal with friends, October is the perfect time to eat your way through paradise.

Prix-fixe menus are available at participating restaurants throughout the Upper Keys. See locations and menus, vote for your favorite Signature Dish, buy Trolley Tour tickets, and more at TasteTheKeys.com.