Wayward Tours

Based in Chicago, Wayward Tours is in the fun business of making cultural connections. We are a small group of food, wine and travel enthusiasts passionate about sharing the delicious flavors and rich history of the coastal Midwest- one bite and town at a time. Together with our partners, we provide immersive 'daycations' featuring guided tours of the best U-pick farms, restaurants, wineries, cider mills and breweries in the Midwest with round-trip transportation from Chicago.