Wayward Tours

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Wayward Tours offers immersive daycations with transportation from Chicago, featuring some of the Midwest's best Farms, Restaurants, Wineries, Cideries & Breweries. ​ While our tour destinations and activities change monthly, you can always expect an array of tastings, farm tours, visits with local experts, and luxury transport to cool coastal towns 1.5-2.5 hours outside of Chicago.Wayward Tours offers immersive daycations with transportation from Chicago, featuring some of the Midwest's best Farms, Restaurants, Wineries, Cideries & Breweries. ​ While our tour destinations and activities change monthly, you can always expect an array of tastings, farm tours, visits with local experts, and luxury transport to cool coastal towns 1.5-2.5 hours outside of Chicago.