Monticello and Wine Trolley Tour

Visit Jefferson’s Monticello and a Vineyard — by Trolley!

$79 | OFFERED BY DEMAND

“Good wine is a necessity of life for me.” -Thomas Jefferson

Jefferson experimented with viticulture and dreamed that Virginia would someday boast its own excellent wines. Today, the estate is indeed surrounded by productive vineyards.

You can experience Jefferson’s legacy with a trolley tour designed to include both his home and his dream of drinking Virginia wine.

Visit Jefferson’s Monticello, tour the house, and then eat a delicious picnic lunch al fresco at a local vineyard. It was Blenheim where Thomas Jefferson and his bride, Martha, are said to have “rested and warmed themselves” after their coach stalled nearby during a snowstorm. Now a vineyard owned and designed by Dave Matthews, Blenheim offers beautiful views and the opportunity to purchase a flight or glass of wine to go with your lunch, since you will be leaving the driving to us!

This is the perfect expression of Jefferson’s vision! You’ll learn about Jefferson and viticulture, but you’ll also experience firsthand the realization of his hopes.

Trolley leaves Crozet at 8:30am, Omni pickup is at 8:55, Amtrak station at 9am, Monticello arrival at 9:30, Lunch at  Blenheim vineyard 1:15, back to hotel at 3pm, Crozet 3:30. Ticket includes the visitor tour of Monticello and a customized picnic lunch from Wegman’s Catering (choose at checkout.) A minimum of 8 riders is required for this tour to take place; tickets would be refunded in the event of low sales.

Monticello and Wine riders also get a same-week discount on an afternoon wine or beer tour with Crozet Trolley Co.


This company is one of the most client-friendly, attentive, and responsive out there! They were flexible with my various requests, were reasonably priced, and they truly went the extra mile when it came to treating my friends and family with grace and courtesy (not to mention a great sense of humor!) I would recommend them highly and will seek them out in all my future trolley / transport-with-charm needs! -Cara C

I was visiting the area from DC with some friends and we were looking for different ways to explore the breweries and vineyards. We heard from some locals that the Uber/Lyft situation wasn't great, so we decided to look for some transportation options. Crozet Trolley was the best deal and seemed like a unique way to see the area, so we decided to go for it. We are so happy that we did! The booking process was really easy and the staff was super friendly throughout the afternoon. It was a great touch to have snacks/water on board, and the discounts at some of the stops were a welcome bonus. Being driven around on the trolley from vineyard to vineyard was the perfect way to spend the day. I can't recommend Crozet Trolley highly enough! - Kevin B.


Experience our regular weekend afternoon wine and beer tours too!