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Charlottesville Travel Guide

Updated: May 4, 2021

Charlottesville, Virginia is one of the cutest towns I have ever visited. November 2019, a few girlfriends and I took a road-trip to Virginia's wine country ready to explore. We had the greatest time and are already planning our next trip back. Charlottesville is a hidden gem full of history, wine and picturesque views. Downtown Charlottesville, home of the University of Virginia, is a must-see; cute boutiques, bars and restaurants. The outskirts of the city are where you'll fine the rolling hills, sprawling vineyards and colonial homes. This Charlottesville travel guide will point you to the must-do things in this history-rich destination.

when to visit

September-November is peak season in Charlottesville. The foliage makes for beautiful photos. Winters in Charlottesville are mild. There is skiing nearby at Wintergreen Resort! (Josh and I have been to Wintergreen and LOVE it. It's a perfect getaway spot.) Travel May-August for quietest time of the year. The students head home for the summer, the gardens at Monticello will be fully bloomed, and you can spend the afternoon tubing on the James River.

where to stay

Because Charlottesville is a college town, there are several hotels to book downtown. The girls and I opted to book an airbnb. We wanted to all be together, not split up in different hotel rooms. Our trip was centered around wine tasting on the outskirts of town. Our airbnb was about 30 minutes away from our vineyard route and pushed back in the woods. We enjoyed a fire-pit in the evenings and the chilly Fall air on our deck overlooking the woods in the morning. Highly recommend looking into an airbnb!

what to do

wine tour

The girls and I went specifically for the wines. There are also several breweries and distilleries. We hired Norm's Executive Transportation to take us on a 5-hour wine tour. Let me just tell you, Norm made our trip. He was so professional, funny and extremely flexible with our wine tour options. He has a few recommendations on his site for vineyards close together to make the most of your tour. 5-hours seems like a long time, but time FLIES when you're having fun. HIGHLY recommend Norm/a car service in general. We will be using him for our trip back in the Spring! (If you book Norm, tell him I sent you!)

head downtown

The downtown mall is one of the most successful outdoor malls in the nation, with over 100 stores and 30 restaurants. There is a mix of historic and modern buildings. Super cute and truly something for everyone!


Visit to Thomas Jefferson's home! Book a guided tour, April-October. There are several types of tours available! Check out this link to see when the botanical garden is in full bloom.

where to eat/drink


*Look to see what events are going on in town before you book anything. UVA's Homecoming football game was happening the weekend we went. Uber's were tough to get, downtown was extremely busy without a reservation and many airbnb's and hotels were booked.

*Map out your trip, depending what you have planned for your trip, you may be spending a decent amount of time in the car. There are vineyards all around Charlottesville, choose wisely ;)

*Double check your wine tour guide will pick you up at your airbnb, Norm's Transportation had no problem with us being a bit further from the vineyards we wanted to visit.

*Book a car service, like I said, Uber's can be tough to get, especially vineyard to vineyard out in the mountains.

Hope this Charlottesville travel guide helps you plan your trip!


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