Windsor Essex Trolley Tours

Leave the driving to us! With so many great wineries to visit in the region, the best solution is to try them all! Whether you’re interested in vineyards, venues, agriculture, history, or attractions, WE trolley provides wine, spirit, culinary, and cultural day tours in Windsor Essex County. Life is about the ride so get on and Trolley On! We offer group tours (we plan it), charters (you plan it), plus the specialized tours below.

Awesome Amherstburg

Enjoy the day with an Amherstburg wine tasting/tour, lunch at the new BeaconHouse walking in Kings Navy Yard and shop at the many fine merchant facilities.$70.

Pelee Island

Hop-On the Trolley and experience the Island life. Enjoy the day with a tour, tastings lunch and sites. $75.

Hop On Tours

Whether you’re a couple looking for a romantic day, an individual looking for an adventure or a small group of friends or family wanting to spend a fun filled afternoon together… Our ‘Hop On Tours’ run on selected dates and depart from various local locations. $75.


Ladies Hop-On the Trolley, Shop at a variety of unique Boutiques; from Shabby Cheek to crafts; gift; garden and greens.Shop at quaint classics while Trolleying though wine country enjoying the food, fare and fun. $62.

519.738.2224 or 519.996.0544,
44 Sinasac St. W, Harrow ON


333 Riverside Drive West, Suite 103
Windsor, Ontario N9A 7C5
Toll Free: 1.800.265.3633