The Charlottesville area in Central Virginia is another top wine region known for its high-quality wineries. It's famous for its exquisite Cabernet Sauvignon, Merlot, and Chardonnay wines. Central Virginia offers not only wine but also a rich cultural experience. You can visit Thomas Jefferson's Monticello, go hiking in Shenandoah National Park, and enjoy farm-to-table dining. The region has a vibrant arts scene and often hosts concerts, theater productions, and art exhibitions.
If you're traveling from a distance, you can book a flight to Charlottesville Albemarle Airport (CHO), which is the most convenient airport for accessing the Central Virginia wine region.
Upon arrival at CHO, rent a car from one of the airport's rental agencies. Having a car is the most convenient way to explore the Central Virginia wine region, as it allows you to visit multiple wineries, attractions, and scenic spots at your own pace.
Charlottesville is the central hub of the Central Virginia wine region and is located a short drive from the airport. Simply follow signs for Route 29, which will take you into Charlottesville.
If you'd rather not drive or prefer a guided experience, you can book wine tours or shuttle services that operate in the Central Virginia wine region. These tours often pick up visitors from Charlottesville and take them to several wineries, providing an easy and enjoyable way to explore the area without driving.
We’ve curated a short-list of boutique hotels perfect for your wine country girls’ weekend. If you want to find a complete list of hotels in the area, visit our partner site to book your stay. Note: many of the boutique hotels we recommend have a nightly amenities fee for some awesome extras included in your stay. Be sure to read the fine print and take advantage of everything included.
Graduate Charlottesville is a vibrant, boutique hotel on historic Main Street. Its amenities include a retro-inspired rooftop bar with panoramic city views, a trendy lobby cafe serving artisanal coffee, and a second-floor game room complete with Foosball and Shuffleboard tables. The hotel also offers complimentary bike rentals for exploring Charlottesville's historic streets, as well as cozy rooms with a modern collegiate theme. The Graduate Charlottesville provides a unique blend of comfort, style, and amenities that ensures an unforgettable stay in this charming Virginia city.
The Doyle Hotel Charlottesville is a vibrant boutique hotel that offers an array of enticing amenities. Savor delicious seasonal bites at the rooftop restaurant with panoramic city views. Unwind with a cocktail at the lobby bar or sample whisky at The Speakeasy. Enjoy morning coffee at the Cafe. Thoughtful touches of original artwork, hand-painted headboards, and floor-to-ceiling windows make every stay extra unique. The Doyle seamlessly blends luxury with artistic flair, ensuring an unforgettable experience for every guest.
Oakhurst Inn is a boutique Charlottesville retreat renowned for its exceptional amenities. Guests relish well-appointed rooms with modern comforts, an outdoor pool, an onsite cafe, and a lobby bar. The inn's thoughtful extras include luxury linens, luxury bath products, and a shared library with a fireplace. With its prime location near the University of Virginia and the vibrant Downtown Mall, Oakhurst Inn provides a blend of sophistication and convenience, making it an ideal choice for a memorable stay in Charlottesville.
Did you know that 59% of US wine consumers are female but only 18% of US winemakers are women? Here at Girlfriend Weekend, we want to support the women breaking down barriers in this industry. When planning your wine country weekend, we suggest a visit to any of the wineries on our list. At the time of publication, all of these producers have a female winemaker at the helm!
Be sure to visit the winery website to check on tasting room hours and if reservations are needed. Some tasting rooms welcome walk-ins, but others require you to call ahead or reserve online. Tasting room experiences can range from a simple tasting to full wine and food pairings and tours of the winery. Check out all the options and plan your visit according to your budget and schedule.
Our last tip is an important one. It’s easy to get swept away by the excitement of it all, but carefully consider how many wineries to visit each day. We recommend 2-3 with a stop for a hearty lunch along the way. Consider hiring a driver for the day, or if you are on a budget, limit the number of places you visit or pick someone as the designated driver!
Louisa VA
Charlottesville VA
Madison VA
Greenwood VA
Crozet VA
Afton VA
We know, wine tasting is the main attraction when you are planning a getaway to wine country. We get it, but we just couldn’t resist calling out a few notable sights to see while you are in the area!
Charlottesville VA
For the ultimate history meets wine‑country moment on your girls’ trip, Jefferson Vineyards is an absolute must. Founded in 1774 by Thomas Jefferson and Philip Mazzei, this historic estate sits right between Monticello and Highland, and today is known for seriously delicious, award‑winning wines like Viognier and Petit Verdot.
The 700‑acre property is pure Virginia countryside magic. You can enjoy year‑round tastings, relaxed food pairings, and gorgeous views across the Monticello AVA. There’s plenty of outdoor seating, from cozy garden patios to wide open fields perfect for picnicking, so bring a blanket and settle in for a dreamy afternoon.
To snack while you sip, order from their tasty selection of cheeses, charcuterie, crackers, and chocolates. For wine, choose from three seasonal flight options, each featuring four unique samples. You can also order wines by the glass or explore a full range of bottles, including special reserve selections.
And for extra vibes, be sure to peek at their website, live music days at the vineyard are the perfect backdrop for a girls’ day out.
Charlottesville VA
For a girls’ trip with a little history, a lot of beauty, and some truly eye‑opening stories, Monticello is an unforgettable stop. Just outside Charlottesville, this mountaintop estate was designed by Thomas Jefferson over four decades and spans 5,000 acres. Today, it’s a UNESCO World Heritage site known for its neoclassical architecture, stunning gardens, and deep, essential historical interpretation of both Jefferson’s life and the enslaved people whose labor sustained the plantation.
Start your visit at the free parking area and the Visitor Center, where you can explore exhibits (including the original Declaration of Independence) before heading up the mountain. The continuously running shuttle gets you there in just five minutes.
Your main experience is the 45‑minute Highlights Tour, which takes you through the first‑floor rooms of Jefferson’s home, the West Lawn, and the South Wing. You’ll learn about Jefferson’s ideas, his complicated legacy, the realities of slavery at Monticello, and the estate’s iconic architecture.
Afterward, take your time exploring Mulberry Row, the plantation’s historic work area. Walk through reconstructed spaces at your own pace or join the powerful Slavery at Monticello Tour to learn more about the enslaved individuals who lived and worked here.
If your group loves gardens or a peaceful moment outdoors, wander the restored flower and vegetable gardens or join a Gardens & Grounds Tour for an inside look at the site’s horticulture and history.
On your way back down, the shuttle offers an optional stop at Jefferson’s gravesite, where he is buried alongside his wife, two daughters, and his son‑in‑law, Governor Thomas Mann Randolph. And if you get hungry, the Monticello Café at the Visitor Center serves seasonal dishes, drinks, and grab‑and‑go bites, with indoor and outdoor seating perfect for a relaxing girls’‑day lunch.
Charlottesville VA
If your girls’ wine trip needs a dose of mountain magic, Shenandoah National Park and the Blue Ridge Parkway are just a short, stunning drive from Charlottesville, making them the perfect day‑trip adventure. Tucked into the beautiful Blue Ridge Mountains, this area is full of jaw‑dropping views, peaceful forests, and trails for every energy level.
Many visitors love taking a scenic cruise along Skyline Drive or the Blue Ridge Parkway, where every overlook feels like a postcard moment. If hiking is more your style, you’ll find hundreds of miles of trails, more than 500 total, including over 100 miles of the legendary Appalachian Trail, the longest hiking‑only footpath in the world.
Shenandoah is dotted with waterfalls, quiet overlooks, and hiking routes ranging from quick, easy walks to more challenging treks. Some great girls-wine-trip‑friendly options close to Charlottesville include:
Charlottesville VA
If you and the girls are looking for a beautiful, easy outdoor adventure near Monticello, the Saunders‑Monticello Trail is the perfect choice. This four‑mile round‑trip path winds through native hardwood forest, rolling ravines, and picture‑perfect views of the Blue Ridge Mountains, all with a maximum grade of just 5%, making it super accessible for walkers, cyclists, and wheelchair users.
It’s open to the public daily, and the trail feels like the ideal mix of peaceful retreat and scenic overlook. Whether you’re in the mood for a relaxed morning stroll, a break between sightseeing stops, or a little fresh air with stunning mountain views, this trail delivers.
There are three parking options depending on where you want to start:
• Route 53 – 503 Thomas Jefferson Parkway (open sunrise to sunset)
• Route 20 – 678 Dairy Barn Road (open sunrise to sunset)
• Monticello’s David M. Rubenstein Visitor Center – 1050 Monticello Loop (open during Monticello’s regular hours)
It’s a peaceful, refreshing way to round out your Wine Country experience, and the perfect nature moment for a girls’ getaway.
Of course, you are going to be buying wine and maybe even joining a wine club or two. But don’t forget about fun boutique clothing, art, gifts, and regional items. Here is a checklist of areas where you’ll find some great shopping.
Charlottesville VA
Downtown Charlottesville is ideal if you are looking to spend the day shopping, strolling, and enjoying the local vibe. At its heart is the historic, eight‑block brick‑paved Downtown Mall (one of the nation’s longest pedestrian malls) filled with locally owned shops and stylish boutiques perfect for browsing together. More than 30 restaurants with inviting outdoor dining make it easy to pause for cocktails, brunch, or a shared dessert between stops. With cultural gems like the Paramount Theater and the McGuffey Art Center adding extra charm, this tree‑lined district creates the perfect backdrop for a relaxed and memorable girls’ shopping outing.
