Taste Downtown, Then Cruise Into the Sunset

Experience two sides of Winter Haven in one memorable afternoon: its local culinary scene and its beautiful Chain of Lakes.

Begin with a two-hour guided walking food tour through downtown Winter Haven. Enjoy curated tastings from locally owned establishments while discovering the city’s history, culture, and hidden landmarks.

Then, trade the downtown streets for the water during a one-hour sunset cruise with Tanner’s Lakeside. Relax, take in the views, and finish your experience surrounded by the natural beauty that makes Winter Haven special.

Adult tickets are $145, or $165 with the drink package. Food tastings are included.

From Downtown Flavors to Lakeside Views

We coordinate the food, stories, and cruise so you can enjoy a complete Winter Haven experience without planning each part separately.

This Experience Is Perfect For

• Couples planning a memorable date

• Friends looking for a distinctive afternoon together

• Birthday, anniversary, and celebration groups

• Locals entertaining visiting family and friends

• Travelers who want to experience more than the theme parks

• Guests who enjoy food, history, nature, and scenic views

What’s Included

• A two-hour guided downtown walking food tour

• Curated tastings from locally owned establishments

• Enough food for a satisfying tasting experience

• Winter Haven history, culture, and neighborhood stories

• Visits to notable downtown landmarks

• A one-hour sunset cruise on the Chain of Lakes

• An optional drink-package ticket

• An experienced, licensed professional guide

Sample Downtown Experience

Your walking tour may include locally prepared dishes, specialty bites, and visits near landmarks such as the Ritz Theatre, Gram Parsons’ Derry Down, and the site connected to Winter Haven’s first Publix.

Specific establishments, dishes, and tour routes may change based on availability.

Your Sunset Cruise

After exploring downtown, settle in for a scenic cruise across Winter Haven’s famous Chain of Lakes. Enjoy the breeze, changing sky, and waterfront views as the day winds down.

Cruise timing and the exact experience may vary because of weather, water conditions, and seasonal sunset times.

Your Local Guide

Your experience is led by a licensed and certified professional guide with more than a decade of experience creating memorable guest experiences in New York City and Central Florida.

Planning a private celebration? Explore our private tours.