29 July, 2021
WanderLove: A Guide to a Girls' Weekend in Charlottesville

WanderLove: A Guide to a Girls’ Weekend in Charlottesville

Wanderlust is defined as a strong need to travel, but here in Virginia we call that feelingWanderLove. And while travel doesn’t look quite the same this year, there’s an epic road trip to explore the endless beauty of Virginia!

Charlottesville is a quaint city with a booming wine scene, indie boutiques, beautiful accommodations, delicious restaurants, and outdoor activities. Its location in the rolling foothills of the Blue Ridge Mountains makes it the ideal getaway for a girls’ weekend. It is also repeatedly mentioned as one of the best, emerging and award-winning wine regions for wine lovers. This charming town is home to nearly 40 wineries and vineyards and is a major producer in Virginia’s wine country. What also makes this wine region unique are the numerous B & Bs and wine experiences in the vineyards – perfect for a safe vacation during this global pandemic. And it’s only a short two hour drive from Washington, DC.


Photo credit: Bram Reusen

No matter where you are driving from, you will know you have arrived in Charlottesville when you see views of rolling hills and mountains, and if you are lucky you will see them peer over the mist. It is an unforgettable sight.

Vineyard accommodation

We arrived in Afton and checked into The Farmhouse at the Veritas Bed and Breakfast. The Farmhouse, built in 1836, offers eight luxurious bedrooms with great views of the mountains and grapevines. Each reservation includes a bottle of sparkling wine and a fresh farmer’s breakfast. I recommend staying in the Derby Room – a modern, two-story, airy room with a view of the Petit Verdot and Viognier vines. The room also has a spiral staircase that leads to the king size bed on the second level. A private entrance leads to a lovely wraparound porch with several rocking chairs. If you can’t stay in the Derby Room, any room is suitable as it is the crème de la crème of B & Bs in the vineyard – especially if you prefer accommodations with charm, elegance and a bit of European flair.


Photo credit: Carlita Pitts IG: @iamthelita

Do you need a bigger room? I recommend booking the Barn Cottage. The vineyard also offers a complete dining experience in three dining rooms equipped for social distancing.

If you want vineyard accommodation with a tranquil resort experience, I recommend the Glass House Winery Bed and Breakfast in Free Union. Free Union is 10 miles northwest of Charlottesville on a hill overlooking the vines and a lake. The scenic view of the Blue Ridge Mountains in the background makes the drive worthwhile.


Photo credit: Carlita Pitts IG: @iamthelita

The Glass House B & B is a group-friendly bed and breakfast with a pool and jacuzzi. The house itself is big, with funky decor and plenty of room to move around. I recommend staying in the Suite to the Stars, a suite with two bedrooms, a living room, a dining area, a kitchen and a large private terrace. Each reservation includes a free wine flight to the winery and some decadent home-made chocolates.

Wineries & Vineyards Near Charlottesville

There are so many beautiful wineries along the Monticello Wine Trail in Virginia that it is difficult to decide which one to visit. If you’re traveling for a girls weekend, make sure the wineries you choose are close together so you don’t drive all over Charlottesville. Pippin Hill Farm & Vineyards is one of my favorites. I have visited several times and it gets nicer every time. The beautiful scenery, the mountain views, the boutique wines, and the farm-to-table menu are unbeatable. During your stay, check out the Blenheim Vineyards owned by Dave Matthews. This beautifully landscaped winery has excellent views of the vineyards and countryside. If you’re in the mood for winery, we recommend stopping by Jefferson Vineyards and Gabriele Rausse Winery.


Also, visit Afton Mountain Vineyards, Barboursville Vineyards, and Stinson Vineyards to learn more about the beauty and scenic views of the Monticello Wine Trail.

Wine experiences Outside of Charlottesville

Do you want to add adventure and great bonding experience to your trip? I would strongly recommend booking a private horseback riding tour through the vineyards with Indian Summer Guide Service. We planned our drive at Veritas after Saturday brunch and it was great. Our horses, Gracie and Amber, were good natured and our guide was very patient with us. When we booked this tour we didn’t realize we were driving up the mountain and when we got to the top we saw the best views of the wineries, farms and properties. It was indeed an unforgettable experience that I would do again in a heartbeat.


Photo credit: Carlita Pitts IG: @iamthelita

Another excellent wine experience to add to your itinerary is the Roseland Polo Match at the King Family Vineyards on Sunday. It’s fun to dress in flowery summer dresses, hats, and wedge heels to watch an action-packed game of polo with the dramatic view of the mountains in the background. Don’t forget to take lots of photos for the gram!

eat in Charlottesville

There are many great restaurants in Charlottesville. Given that Charlottesville is in the south, it is best known for Mediterranean cuisine like fried chicken, smoked BBQ, and black-eyed peas.

While we wanted great food on our trip as it is a girls weekend, we also wanted to dine in trendy restaurants with great views. On Friday night we ate at the Common House, the only contemporary member’s social club. It is beautifully designed and has a multi-purpose function room, networking lounge, library, game room and rooftop terrace. In the evening it rained so we couldn’t see the roof terrace. However, we enjoyed our meals while there and we were equally impressed with the decor and service.

We ate at the Quirk Hotel in downtown Charlottesville on Saturday night. The Quirk is one of the newest boutique hotels in Charlottesville, opening earlier this year. It is a modern hotel with a chic, artistic feel. Upon entering, you will notice the curvaceous ceiling, a large art gallery, two restaurants, and a coffee shop.

We ate in the rooftop bar which was just as stylish as it was beautiful. Like the rest of the city, the rooftop bar had lovely panoramic views of downtown Charlottesville and the Blue Ridge Mountains. The restaurant offers a rustic Italian menu with pizza, oven vegetables, pasta, cold meats and cheese. They also source local craft beer and wine from the Virginia wineries.

I will never forget my trip to Charlottesville and the surrounding wineries with my girls. In fact, we enjoyed it so much that we are already planning our next visit!

THIS GUEST BLOG POST is courtesy of Carlita Pitts, a Northern VA wine lover, wine lover, and travel enthusiast. She is the main content creator of Divine Lita, a blog about vineyards, wine, and travel – which primarily highlights her experiences in the Virginia, DC and Maryland wine regions. Visit her blog or catch her on Instagram @iamthelita to find out more.

WanderLove: A Guide to a Girl’s Weekend in Charlottesville first appeared on Virginia’s travel blog.

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