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We specialize in small group tours and deliver a truly unique experience. Cruising through the County in a classic Cadillac with the top down while your favourite tunes play through the speakers is a perfect way to experience the incredible wineries, breweries and extensive sights PEC has to offer.

Our Tours

The County covers a huge area and wineries are spread out East to West. While there are many gems hidden in by-the-way spots, we want to maximize your experience and spend most of your times at the wineries themselves rather than driving all over the place. The cars are great don't get me wrong, but you're really here for the wine. In order to get the most bang for your buck we have chosen select wineries grouped around popular accommodations. Leave it all to us, there are no decisions to be made except of course which wine you'd like to try- we pick you up and drop you off and in between you'll hit 4 wineries.

We choose wineries based on location, and also the best possible experience for you to have. What would we want if we were touring the county? Great wine, fantastic tunes, a beautiful car and lots of fun, so that's what you get with us.

Make sure you download your favourite playlists as each of our classic cars comes with a bluetooth speaker to ratchet up the fun factor. Water will be provided during your tour. Come ready to have a ton of fun, enjoy the beauty of Prince Edward County, all from the backseat of one of our classic beauties. Try to keep your hands and feet inside the vehicle at all times, things tend to get a little wild!

Contact us for pricing

Pickups outside our normal radius may be subject to a fuel surcharge.

We can accommodate up to 20 people, and tasting are not included in the tours.

 (416) 876-2751 (text for quickest response)
Guests are raving about Vintage Car Wine Tours!
We had such a fantastic day touring the various vineyards and distillery with Sam and the gorgeous 1960 Buick LaSabre!! Sam provided the perfect music mix for the road and everyone turned heads when we drove by. I highly recommend hiring Sam's Vintage Wine Tours. Sam is a wonderful soul with excellent knowledge of the area, cars, and music! We cannot thank you enough Sam for the wonderful experience you provided for us!!
- Joe H
I will never be able to put into words how great this wine tour was! My husband and I had never been to PEC before and booked a Vintage Car Wine Tour as a fun way to celebrate our mini honeymoon. I couldn’t pick a car and asked to be surprised! Our guide Sam rolled up to our hotel in a 1961 Cadillac DeVille which was the perfect way to feel like a “main character” if you catch my vibe! Our guide Sam was incredible, he was fun, energetic, hilarious, super knowledgeable about the area and just “got it”. At each winery he made sure we were seated immediately and taken care of before he would leave us to enjoy our wine tastings. He was honestly such a highlight, coolest guy to spend the day touring the county with! 10 out of 10 would recommend this tour a million times over!
- Caitlin Taylor
If you’re looking for an unforgettable way to experience the best of the county, look no further! Booking was a breeze with Sam, and our driver Marty was so personable and flexible, offering us a unique and custom experience of hopping from winery to winery for my 30th birthday. Everyone knows these guys and you get treated like VIPs everywhere you go. Not to mention the cars make for an amazing way to travel around. Will be recommending to all our family and friends when in the county. Thank you Sam and Marty!
- Patricia Chiodo
What better way to celebrate an 80th birthday than cruising beautiful Prince Edward County in a pristine, turquoise '61 Cadillac DeVille, windows open, hair blowing in the wind (well...those of us with hair, sorry Dad), listening to rock n'roll favorites? Better still, driven and accompanied by the charming, one and only Sam Grosso. Truly an enjoyable afternoon and memorable day! Thank you Sam.
- Shelly MK
Had a lovley date with my husband in Sam Grosso's vintage beauty! Can't think of a more wonderful way to take in PEC! You can either create your own tour or let Sam do the planning for you. From a tasting and behind the scenes tour of Casa Dea, to a relaxed Muskoka chair Hinterland peach Bellini, from honey mead and photos with the lavender at Millefleurs, to a Midtown Brewery pizza and beer take out window - it was the perfect kinda day :) Great playlist, conversation and so much fun. Highly recommend this tour!
- Kristen Whalen
My husband and I took a tour in the vintage Cadillac convertible for our honeymoon in the County. We absolutely loved it! Sam made the experience so special and we highly recommend to anyone looking for a unique and personal experience! Can't wait to make this a yearly trip!
- Melissa Margaret
This was the best wine tour I've ever been on (and I've been on my fair share)! Not only was the vintage car a great way to travel, Sam is so familiar with the best wineries and their owners. We were treated like VIPs. Can't wait to do it again!
- Samantha Sandford
Such a great way to end the last weekend of summer, driving around in a 1969 caddy convertible with our gracious host Sam. The wineries we visited were great. A fun filled day with lots of wine tasting, great food and conversations with friends and of course loving all the attention everyone gave to the vintage car as we approached. We will definitely book another tour soon.
- Carmela Puopolo
We recently booked Vintage Car Wine Tours for a bachelorette weekend and highly recommend the tour for your next PEC getaway! Great choice of wineries, easy to book, lovely hosts and badass rides. Can't say enough great things about our experience!
- Kerri Payton-Stewart
This is a MUST DO new offering in the County. "Gentleman" Sam is an intelligent and gracious host. The wineries he chose were fabulous. Wine tasting and food with great conversation and having everyone oooh and aaah about your wheels. What is not to love?
- Kathleen Leach
What an amazing experience! The only thing cooler than the vintage ride was the enthusiasm and passion from our host Sam. What a fun way to see and learn about the beautiful winery’s PEC has to offer! I had so much fun cruising around with my girlfriends, a Day date with my boyfriend seems like the perfect excuse to do it all over again :)
- Alicia Sutton
Our Cars
Choose any of our vintage cars when you create your personal Vintage Care Wine tour!
1937 Oldsmobile
1954 Mercury Monterey
1961 Cadillac
1969 Cadillac
1969 Lincoln
1961 Lincoln
ABOUT SAM, FROM SAM

So one morning I get up at the crack of dawn as usual- I have no idea why but I just can't sleep in, my father was the same.

I clean the kitchen, make my kids and wife breakfast and start thinking of all the times I've been asked his last year, "So how's retirement? ". Now let me tell you nothing makes you feel old as someone saying that to you.

It doesn't help that I listen to music from the past four decades and still get excited about it like a 16 year old in 1964 experiencing the Rolling Stones for the 1st time. I love vintage clothes and cars too. I wasn't meant to be born in 1968- I should've been born in the 40's so I could have enjoyed the 50's and 60's at that time instead of many decades later.

A while back I saw an ad about vintage car tours in Manhattan and it sparked an idea. I have been collecting vintage cars since I was a young man. For nearly a decade I've been living in Prince Edward County, and since I sold my bar/music venue, The Cadillac Lounge in Toronto last summer I've got some time on my hands. I've always been an idea person who flies by the seat of my pants. So now I have some time to figure out what I'd like to do. I'm still involved in the music scene but going at my own pace and with Covid, that's slowed down too. But this thing in Manhattan made so much sense to me- it combines my love of vintage cars, great music and the beauty of where I live and what I love about this area. Prince Edward County is a wonder and I love nothing more than driving around with my wife in our old cars exploring parts of the County I've never been before. It all came together so seamlessly and folks are digging it.

Honestly this doesn't feel like work, it's a pleasure. I've always loved helping to make people happy- I did it in the bar business for 25 years and now I'm doing it again in different ways. I'm not much of a business guy, I didn't go to business school but I've always just treated people the way I would want to be treated and it's worked out well for me. And the fact it allows me an excuse to keep buying vintage cars without my wife rolling her eyes (too much), is a bonus!

Besides the booming business and looking for drivers to help out with the demand of the tours people are seeking I'm also looking a bit down the road. The long game I guess is also to teach my kids work ethic and that their Dad is not some international man of mystery that does nothing but taxi them around to school & play dates. I'm still a cool-rocking'- Daddy driving kick-ass cars trying to spread some joy.

Our Friends
Thank you to all of the Vintage Car Wine Tours great friends.