Wanderlust is defined as a strong desire to travel, but here in Virginia, we call that feeling WanderLove. Explore Virginia’s endless beauty with an epic road trip!

Charlottesville is a picturesque city with a booming wine scene, indie boutiques, beautiful accommodations, tasty eateries, and outdoor activities. Its location in the Blue Ridge Mountains’ rolling foothills makes it the ideal getaway for a girls weekend. It is also consistently mentioned as one of the top, up-and-coming, award-winning wine regions to visit for those who love wine. This charming city is home to nearly 40 wineries and vineyards and is a significant producer in Virginia's wine country. What also makes this wine region unique is the numerous vineyard B&Bs and wine experiences. And it's just a short two-hour drive from Washington, D.C.!


Photo Credit: Bram Reusen

No matter where you are driving from, you will know that you arrived in Charlottesville when you see views of rolling hills and mountains, and if you're lucky, you'll see them peeking above the fog. It is a sight to behold.

Vineyard Lodging

We arrived in Afton and checked-in to The Farmhouse at Veritas Bed and Breakfast. Built in 1836, The Farmhouse offers eight luxurious bedrooms with stunning views of the mountains and grapevines. Each reservation includes a bottle of sparkling wine and a fresh farm breakfast. I highly recommend staying in the Derby Room — a contemporary, two-level, airy room with views of the Petit Verdot and Viognier vines. The room also has a spiral staircase, which leads to the king bed on the second level. A private entrance leads to a beautiful wraparound porch, which includes multiple rocking chairs. If you're unable to stay in the Derby Room, any room will do, as it is the crème de la crème of vineyard B&Bs — especially if you prefer accommodations with charm, elegance, and a bit of European flair.


Photo Credit: Carlita Pitts, @iamthelita

Need a larger space? I recommend booking the Barn Cottage. The vineyard also offers a full dining experience in any three indoor dining spaces equipped for social distancing.

If you desire a vineyard accommodation with a tranquil, resort experience, I recommend Glass House Winery Bed and Breakfast in Free Union. Free Union is ten miles northwest of Charlottesville and is located on a hill overlooking the vines and a lake, plus the scenic views of Blue Ridge Mountains in the background make the drive worth it.


Photo Credit: Carlita Pitts, @iamthelita

Glass House B&B is a group-friendly bed and breakfast with a pool and hot tub. The house itself is large, with funky décor and lots of space to move around. I highly recommend staying in the Suite to the Stars, a two-bedroom suite, with a living room, dining area, kitchen, and a large private deck. Each reservation comes with a complimentary wine flight at the winery and some decadent chocolates made in-house.

Wineries & Vineyards Near Charlottesville

There are so many beautiful wineries along Virginia's Monticello Wine Trail that it's hard to choose which to visit. If you're traveling for a girls’ weekend, be sure that the wineries you select are near each other, so you aren't driving all over Charlottesville. Pippin Hill Farm & Vineyards is one of my favorites. I've visited multiple times, and it gets prettier each time. You can't beat the beautiful landscaping, mountain views, boutique wines, and farm-to-table menu. While you're out there, check out Blenheim Vineyards, owned by Dave Matthews. This beautifully designed winery has excellent views of the vineyards and countryside. If you're up for winery hopping, I'd suggest stopping by Jefferson Vineyards and Gabriele Rausse Winery.


To experience more of the Monticello Wine Trail's beauty and scenic views, be sure to also visit Afton Mountain Vineyards, Barboursville Vineyards, and Stinson Vineyards.

Wine Experiences Outside of Charlottesville

Want to add adventure and a great bonding experience to your trip? I'd highly suggest booking a private horseback riding tour through the vineyards with the Indian Summer Guide Service. We planned our ride at Veritas after Saturday brunch, and it was terrific. Our horses, Gracie and Amber, were well-mannered, and our guide was very patient with us. When we booked this tour, we didn't realize we were riding up the mountain, and when we got to the top, we saw the most beautiful views of the wineries, farms, and properties. It was indeed a memorable experiermnce that I would do again in a heartbeat.


Photo Credit: Carlita Pitts, @iamthelita

Another excellent wine experience to add to your itinerary is the Roseland Polo Match at King Family Vineyards on Sundays. It's fun to get dressed up in floral sundresses, hats, and wedge heels to watch an action-packed polo match with the background's dramatic mountain views. Don't forget to take lots of photos for the ‘gram!

Dining in Charlottesville

There are many great places to dine in Charlottesville. Given that Charlottesville is in the south, it's most known for southern cuisine such as fried chicken, smoked BBQ, and black-eyed peas.

While we wanted great food on our trip, given that it is a girls’ weekend, we also wanted to dine at trendy restaurants with great views. On Friday night, we ate at Common House, a contemporary member's only social club. It is beautifully designed, with a multipurpose event space, networking lounge, library, game room, and roof terrace. It rained the evening we went, so we didn't get to see the roof terrace. However, we enjoyed our meals while we there, and we were equally impressed by the décor and service. 


photo credit: Kate Thompson

On Saturday evening, we dined at the Quirk Hotel in downtown Charlottesville. The Quirk is one of Charlottesville's newest boutique hotels, opening earlier this year, and is a modern hotel with a chic, artsy atmosphere. Upon entering, you'll notice the curvaceous ceiling, a large art gallery, two restaurants, and a café.

We dined at the rooftop bar, which was just as stylish as it is beautiful. Like the rest of the city, the roof bar had lovely panorama views of downtown Charlottesville and the Blue Ridge Mountains. The restaurant offers a rustic Italian menu serving pizzas, oven-fired vegetables, pastas, charcuterie, and cheeses. They also locally sourced craft beer and wine from the Virginia wineries.

I’ll never forget my trip with my girls to Charlottesville and its surrounding wineries. In fact, we enjoyed it so much, we’re already planning our next visit!

THIS GUEST BLOG POST IS COURTESY OF Carlita Pitts, a vineyard loving, wine sipping, travel enthusiast living in Northern VA. She is the chief content creator of Divine Lita, a vineyard, wine, and travel blog – which mostly highlights her experiences visiting the wine regions in Virginia, DC, and Maryland. Visit her blog or catch her on Instagram @iamthelita to learn more.