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.Take a look at our Windsor online trip builder to schedule your visit to Windsor Essex Trolley Tours and learn about what else to see and do during your holiday.
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.
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.
Windsor Essex Trolley Tours reviews
Our ride and driver were fantastic but our experience at the wineries left a sour taste in our mouth. We visited three wineries had a total of 10 Oz of tasting and our lunch consisted of a bowl of... more »
We have taken the trolly tours and had a wonderful time. We visited several wineries and had a lovely dinner at the last winery where the chef came out and chatted with everyone. The driver and... more »
Plan your trip to Windsor
Get a personalized tripA complete day by day itinerary
based on your preferences
Customize itRefine your trip. We'll find the
best routes and schedules
Book itChoose from the best hotels
and activities. Up to 50% off
Manage itEverything in one place.
Everyone on the same page.
Popular things to do in Windsor
Side trips from Windsor
Parks in Windsor
Hidden gems in Windsor
Breweries & Distilleries in Windsor
Nearby attractions in Windsor
Trips in Windsor by other users
2 days in Windsor BY A USER FROM UNITED STATES Walkerville Artist Co-op · Distillery Tours · Olde Walkerville Neighborhood 2 days in Windsor BY A USER FROM CANADA Point Pelee National Park · Serenity Lavender Farm · Oxley Estate Winery 2 days in Windsor BY A USER FROM CANADA Point Pelee National Park · Serenity Lavender Farm · Oxley Estate Winery 22 days in Windsor BY A USER FROM CANADA Distillery Tours · Olde Walkerville Neighborhood · Walkerville Artist Co-op 2 days in Windsor BY A USER FROM CANADA Point Pelee National Park · Serenity Lavender Farm · Oxley Estate Winery 3 days in Windsor BY A USER FROM CANADA Windsor Sculpture Park · Windsor Riverfront · Dieppe Gardens