3 DAY ITINERARY IN CHARLOTTESVILLE, VIRGINIA: THE PERFECT ITINERARY FOR YOUR FIRST VISIT

I visited Virginia in 2019 experiencing the best wineries in Orange, and Charlottesville. It was so nice to get a chance to go back, but this time with my baby. During my recent trip to Charlottesville, we spent 3 full days exploring the best things to do in Charlottesville.

I’m excited to share my 3-day itinerary with you, which is perfect for your first visit.

WHERE TO STAY

Located in Downtown Charlottesville, The Quirk Hotel was the perfect hotel during our stay. The property is quite unique, with its own art gallery, a rooftop bar, and a beautiful design. The hotel is kid-friendly, they provided us with a sound machine and a pack-n-play.

During our stay, Babyation also provided me with a breast pump. The customer service team is amazing. They did a 1:1 session with me to help with setup and to answer questions. What I really liked is the Pump’s enclosure holds everything you need to take with you so it actually weighs less than pretty much any other pump (when you include the cooler, extra bags, extra parts, etc.) and is great for being on the go.

It’s also super easy to clean and it also has its own app that controls the pump, tracks inventory, and has an auto start/stop feature.

DAY 1

Fly to Charlottesville Airport & pick up the car rental. Charlottesville is a quick-hour flight from New York City, which makes it super convenient when traveling with young children. All activities during our trip were no more than 20 minutes away by car.

Lunch at the Dairy Market. The Dairy Market is a 15-minute walk from the hotel or a short drive. It’s super cute, with lots of food vendors with outdoor seating. What to order: Fried fish from Angelic’s Kitchen and corn pudding. Trust me, this was amazing!

Explore Charlottesville’s Downtown Mall. The Downtown Mall has more than 120 shops and 30 restaurants housed in historic buildings along the city’s Main Street. We were here almost every day, there are great restaurants, shops, and live music. Below is a list of recommendations:

Virginia Discovery Museum – small children’s museum emphasizing discovery with interactive exhibits in art, history & science. We did not have time to visit, but really wanted to make it here!
Telegraph Art & Comics – independent bookstore
Alakazam Toys – independent toy store
Ix Art Park – explore the outdoor murals/create art

Dinner on the rooftop at The Quirk Hotel. The rooftop is perfect for sunset and the food was really good and fresh!

DAY 2

Breakfast at Iron Paffles & Coffee. Highly recommend going here! It’s a puff pastry waffle sandwich and I really liked the coffee here.

Carter Mountain Orchard for apple picking. This orchard was so much fun and also on a mountain top so it has amazing views! I suggest leaving any strollers in the car and bringing a baby carrier with you as you will be walking up a hill to go apple-picking. They also have pumpkins, and the apple cider donuts are a must!

Lunch at Pippin Hill Farm & Vineyard. I also visited this winery during my first visit to Virginia in 2019 and it’s my favorite winery! The views are stunning, you’ll want to take plenty of photos here. The food is also fresh, many of the items on the menu are grown directly from their garden. The wine paired perfectly with the food, I recommend the sliders, fish tacos, and cheese plate. The winery is also great for special events and weddings.

Dinner at Fleurie. The restaurant offers a daily three-course prix-fixe menu for $95, the food was delicious!

DAY 3

Breakfast at MarieBette Bakery. I suggest getting the avocado toast!

Visit Monticello’s Saunders-Monticello Trail. This is a great stroll and perfect for walks with a stroller.

Lunch at Michie Tavern. It’s a historic landmark, an 18th-century-style pub. They currently offer a Southern Midday Fare buffet. The fried chicken might be the best-fried chicken I’ve ever had! They’re open from 11:30-3:00.

Visit Eastwood Farm & Winery. This winery is kid-friendly and woman-owned and operated. Adults can get wine flights while the kids get juice flights.

Dinner at Broadcloth. Located at The Wool Factory, this restaurant is open from Thursday to Saturday and offers 3 menu options: 4 courses ($60), 6 courses ($90), and Chef’s Tasting ($135). Highly recommend it if you’re visiting from Thursday to Saturday!

I hope you found my 3-day itinerary in Charlottesville, Virginia helpful in planning your trip! Charlottesville is the perfect destination for everyone including families and couples, and it would also make a great girls’ trip!

It was the best first trip with Asher, I loved how easy it is to get around and the food was incredible! 3 full days in Charlottesville was just perfect. If you have any questions, please leave a comment below!