3-Day Tour: Pelee Island Sightseeing + Curated Tasting Trail
2 x Wine Tastings • Whisky Tasting • Cider Tasting • Cheese Tasting • 2-Nights Accommodation at the beautiful Caesar's Windsor Casino Resort & Hotel

  • This tour is restricted to adults 19+.
  • ​This tour is entirely in Canada. Passports are NOT required.​
Trade the everyday for three unhurried days along Ontario's southernmost shores, where Lake Erie's warm microclimate ripens some of Canada's finest grapes — and where a whole trail of local makers is waiting to pour, plate, and pair their best for you.

This isn't a winery-lunch-and-back day trip. It's a curated tasting journey. Over three days you'll savour five distinct tasting experiences: a structured wine tasting with pairings at a celebrated area winery, award-winning spirits at Windsor's own Wolfhead Distillery, a flight of three craft ciders at a local cidery, a hands-on cheese tour and tasting at the renowned cheese dairy, and a boxed lunch with wine tasting at the Pelee Island Winery Pavilion — set right among the vineyards on the island itself.

The centrepiece is Pelee Island. We cross by ferry — a relaxing 90-minute sail each way — to explore Canada's southernmost inhabited point on a narrated tour led by a local guide who knows every story this little gem has to tell, from its shipwreck-dotted shores to its rare wildlife and centuries-old winegrowing heritage.

Between tastings, you'll settle into the four-diamond comfort of Caesars Windsor Resort & Casino for two nights, with the waterfront, dining, entertainment, and gaming floor all just steps from your room. Each morning starts with breakfast vouchers to use at your leisure.

​Throughout, your ShortTrips.ca Tour Director travels with you to handle every detail, so all you have to do is relax and enjoy.

Tour Dates

3-Day Trip
July 15-17, 2026
​Aug 30-Sep 1, 2026

Price

Only $99 deposit to reserve your seat. Deposit is fully refundable if you cancel for any reason by the cancellation deadlines shown further down this page.
All prices are per person, in Canadian dollars. ​All taxes and tips are included!
  • Double $849
  • Triple $799
  • Quad $749
  • ​Single $989
For explanation of the words Double, Triple, Quad & Single click here

Pickup Locations

7:15 AM Vaughan Carpool Lot
8:00 AM Scarborough Town Centre
8:40 AM York Mills Station
9:15 AM Mississauga Carpool
9:30 AM Mississauga McDonalds Hurontario & Courtney Park Drive
To book over the phone
please call (866) 208-2950

Inclusions

  • Round trip transportation on a highway motorcoach with a washroom and WiFi.
  • Two night's hotel accommodation at the deluxe Caesar's Windsor Casino Resort & Hotel included.
  • Ferry ride to/from Pelee Island included.
  • Boxed lunch with wine tasting at Pelee Island Winery Pavilion included. You will receive an email requesting your preferred meal selection closer to the trip date.
  • Narrated bus tour of Pelee Island with local tour guide included.
  • Structured wine tasting with pairings at an area winery included.
  • Structured spirits tasting at a distillery included.
  • Structured cider tasting at a cidery included.
  • Tour & tasting at a cheese dairy included.
  • $20 in breakfast vouchers at Caesar's Resort included.
  • Escorted tour with ShortTrips.ca tour director available during the tour.
  • All tips & taxes included.

Approximate Return Times

  • Mississauga Carpool 5:30 PM
  • Mississauga McDonalds 5:45 PM
  • York Mills 6:35 PM
  • Scarborough 7:05 PM
  • Vaughan 7:45 PM

Deposits, Payments, Cancellations & Refunds

  • $99 deposit required to reserve your seats. Deposit is fully refundable if you cancel for any reason by the deadlines in the table below.
  • Reminder emails will be sent a few days before the due date for the final payment. Final payments are not refundable once paid. 
  • If the tour has to be cancelled due to travel restrictions or government shutdowns, a full & prompt refund will be done regardless of how many days are left before departure.
  • You can transfer your seat to anyone else you know up to the time of departure without penalty, there is no cost for name changes.

​Cancellation Deadline/Final Payment Dates

Tour Date
Cancellation Deadline & Final Payment Due Date
July 15-17, 2026
June 15, 2026
Aug 30-Sep 1, 2026
July 30, 2026

Notes

  • This tour is entirely in Canada. Passports are NOT required.
  • Government issued photo ID is required for entry to Caesar's since it is also a casino. Driver's licence, OHIP card, passport etc. are all acceptable. 

Travelling With Children

  • Sorry, this trip is restricted to adults 19+. 

Trip Highlights

Pelee Island

Did you know that Pelee Island is on the same line of latitude as Northern California? That explains why Pelee Island wines are so good!

We will be taking the ferry from Leamington, Ontario to travel to Pelee Island, the southernmost point of Canada, Our bus will be coming with us on the ferry! Yes, it's a big ship.

​Once we arrive on Pelee Island, we will proceed to the Pelee Island Winery Pavilion for our lunch on the winery patio followed by a guided bus tour of Pelee Island with a local tour guide before we return on the ferry to the mainland. 

Pelee Island Ferry

A ferry ride to Pelee Island is something special. Everything changes the moment you pull away from the dock. The ship cuts through the warm waters of Lake Erie and your cares drift away in her wake. 

Relax on the top deck and bask in the sun. The ship also has a large indoor climate controlled seating area if that is your preference and a snack counter if you should feel a bit peckish. 

Wine Tasting

Located in a pristine setting, the vineyards are an estate winery located on the Lake Erie North Shore viticulture region. 
We will be doing a structured tasting and each wine will be accompanied by a paired nibble to bring out the best in the wine.

Of course you will also have an opportunity to tour the beautiful grounds as well as shop for wines and other products in their retail store.

Wolfhead Distillery

Wolfhead Distillery is a true craft operation, incorporating the resources found in their own backyard to produce unique flavours that push the boundaries of Canadian Spirits.  They currently have 8 unique premium spirits and are known for their double barrel Whisky  and small batch Vodka. 

We will be tasting 4 of their very interesting flavoured spirits in an instructor led session and then, again, you will have an opportunity to do some shopping in their gift shop if you feel so inclined.

Caesar's Windsor

Just about as close as you can get to a Las Vegas style hotel without actually going to Las Vegas! This stunning hotel overlooks the Detroit River and features an on-site casino, a 10,000 m² fitness center, and a full-service spa. All modern rooms feature a 42-inch flat-screen HDTV, free Wi-Fi throughout, elegant linens and pillow-top mattresses, the guest rooms have a refrigerator, a coffee machine, a safe and ironing facilities. 

Your tour package includes 2 breakfast vouchers, $10 each.