• Our unique Connections Program
• Private coach transportation
• 3 nights accommodation
• 3 breakfasts, 2 lunches, 1 dinner
• Local professional guides and all entry fees and passes for the listed highlights
• Services of a Professional Tour Director

Prices are in Canadian dollars, are per person, and include HST.

INCLUDED HIGHLIGHTS

• Stay at the incomparable Caesars Windsor
• Rum Runners Tour
• Guided tour of Pelee Island
• Wine tasting
• Free evenings to enjoy the casino

Rum Runners Tour

Now this is fun! Join a cast of colourful characters as you dive into the captivating world of Windsor’s Prohibition past. Hear lively tales and visit key sites tied to the infamous rumrunners— from notorious hideouts to the grand mansions of those who profited from the trade. You'll even enjoy lunch at a speakeasy-style venue, where “Fingers” will be tickling the ivories with jazzy tunes straight from The Roaring Twenties.

Pelee Island 

Begin with a scenic ferry ride to Canada’s southernmost point, where you'll discover how the island’s unique climate and geography create ideal conditions for wine production. After a relaxing lunch, take a leisurely and informative tour of this hidden gem, rich in natural beauty and local charm.

A Delightful Getaway!

Get ready to be whisked away from the everyday into a world of discovery and delight! From the vibrant energy of Caesars Windsor, with its world-class casino and entertainment, to the intrigue of Prohibition-era rum-running, and the serene beauty of peaceful Pelee Island, this getaway offers a rich blend of excitement, history, and relaxation. It’s a tour filled with fun and games, fascinating stories, and unforgettable experiences.

Day 1: Travel to Windsor

Journey westward across Southern Ontario to Windsor, where your home for the next few days is the luxurious  Caesars Windsor Hotel & Casino. Freshly renovated rooms offer timeless elegance and comfort, complemented by upscale amenities throughout the property. Enjoy a variety of on-site restaurants, live entertainment, and, of course, the thrill of the casino floor, featuring 85 table games and over 2,200 slot machines. Kick off your getaway with a 4-star welcome dinner, a perfect opportunity to meet your fellow travellers. Then, take some time to explore the lively atmosphere of the casino at your leisure.

Stay: Caesars Windsor, Windsor, ON (3 nights)

Meals: D 

Day 2: Windsor Rum Runners Tour, Free Evening at the Casino

After breakfast, step back in time on the Rum Runners Tour, more of an adventure than a traditional tour! Travel to the Roaring Twenties, an era of bootleggers, gangsters, speakeasies, and blind pigs. A colourful cast of characters will guide you through Windsor, sharing tales of hidden bootlegger hideouts and mansions built with rumrunning profits. Even iconic landmarks like the courthouse, Ambassador Bridge, and United Methodist Church played their part in this storied past. After your time-travelling adventure, return to the hotel with free time for dinner and an evening of fun at the casino.

Meals: B, L

Day 2 & 3 may be reversed depending on the ferry schedule 

Day 3:  Pelee Island Tour & Wine Tasting, Free Evening at the Casino

After breakfast, spend a relaxing day on the beautiful, serene Pelee Island, the southernmost landmass in Canada. Discover how the island's unique features create ideal conditions for growing grapes, and learn about its significance for migrating Monarch butterflies and songbirds. Enjoy a delightful lunch while sampling a variety of wines. In the evening, return to your hotel in Windsor. Share dinner and stories with new friends from the day’s adventure, then perhaps try your luck at the casino or unwind with the evening at your leisure.

Meals: B, L

Day 4: Homeward

Enjoy breakfast at the hotel, then it’s back aboard the coach for the journey homeward. What was your favourite part of the trip: the Rum Runners, the casino, or Pelee Island?  You’ll never look at the Ambassador Bridge the same way again!

Meals: B

This tour includes our unique Connections Program, and follows a special travel Route A, picking up in the following locations:

• Lindsay
• Peterborough
• Bowmanville
• Whitby 
• Markham
• Brampton
• Milton
• Cambridge
• Woodstock
• London 

While this tour is based in Windsor, Ontario, our Connections Program allows us to welcome guests to join from anywhere in the world! Please contact us to discuss your travel alternatives, airfare and pre-and post-tour accommodation options.

For the ferry ride on this itinerary, some people may want to bring along their remedies for motion sickness. You don’t want to let a little thing like that spoil these amazing experiences.

The Rum Runners was very unexpected; very well done, lots of fun!

– S. Thomson

Pelee Island was the attraction (to the tour), but the Rum Runners Tour ended up being the highlight – fantastic day! 

– M. Pendlebury

Length of the tour was good for a first trip and the price was reasonable.

– S. Prosser