Charlottesville is a town that effortlessly blends history, culture, nature, and charm—and when you stay at The Inn at 400 West High, you’re right in the heart of it all. Whether you’re here for a romantic weekend, a solo retreat, or a mini vacation with friends, here’s a two-day itinerary to help you make the most of your visit.
Day 1: Dive into History and Local Flavor
☕ Morning: Coffee + Stroll at the Downtown Mall
Start your morning with a short walk from the Inn to the Historic Downtown Mall, one of the longest pedestrian malls in the country. Grab a latte and pastry at Mudhouse Coffee or Grit Coffee, then explore the charming local boutiques, bookstores, and galleries that line the brick-paved street.
🏛️ Late Morning: Monticello Tour
A visit to Charlottesville isn’t complete without seeing Thomas Jefferson’s Monticello. Just five miles from the Inn, this UNESCO World Heritage site offers fascinating insight into Jefferson’s life, architecture, and legacy. Be sure to book tickets in advance!
🥗 Afternoon: Lunch with a View
Head up to Michie Tavern, just around the corner from Monticello, for a historic lunch experience with 18th-century Southern fare, or return to town for something lighter like The Fitzroy or Revolutionary Soup.
🍷 Late Afternoon: Wineries or Breweries
Charlottesville is home to some amazing wineries and breweries. For a relaxed afternoon, visit King Family Vineyards or Jefferson Vineyards for a tasting with scenic views. Prefer craft beer? Try Three Notch’d Brewing Company, just minutes from the Inn.
🍽️ Evening: Dinner Downtown
Enjoy a memorable dinner at The Alley Light (a cozy, Michelin Guide–recommended spot) or Tavola, a local favorite for rustic Italian cuisine. Both are walkable from the Inn and perfect for an intimate night out.
🛏️ Nightcap: Back at the Inn
After a full day, return to your peaceful room at the Inn. Curl up with a movie on your flat-screen TV, enjoy a cup of tea or glass of wine, and relax into the comfort of your beautiful linens.
Day 2: Local Art, Nature, and UVA Culture
🥐 Morning: Breakfast at the Inn
Wake up refreshed and start your day with a delicious breakfast prepared right at the Inn. Enjoy freshly brewed coffee, fruit, and local specialties in a cozy, sunlit setting.
🎨 Mid-Morning: Art + Culture
Visit the McGuffey Art Center or IX Art Park—both great spots to see local artists at work or snap some vibrant photos. If you’re here on a Saturday, check out the Charlottesville City Market for fresh produce, crafts, and homemade goodies.
🏛️ Afternoon: University of Virginia Grounds
Take a self-guided tour of UVA’s beautiful campus, designed by Thomas Jefferson. Walk the iconic Lawn, peek into the Rotunda, and stop by the UVA Chapel. It’s peaceful, historic, and architecturally stunning.
🍕 Lunch on the Corner
Pop over to “The Corner,” UVA’s bustling student hub, for a casual lunch. Try Bodo’s Bagels, Take It Away, or Mellow Mushroom.
🌄 Late Afternoon: Scenic Drive or Nature Walk
If you have a car, take a short drive to Carter Mountain Orchard for panoramic views (and delicious apple cider donuts), or visit Rivanna Trail for an easy nature hike close to town.
🌅 Evening: A Relaxing Wrap-Up
Have a laid-back dinner at Oakhart Social or enjoy small bites and cocktails at Common House. Then return to the Inn for your final peaceful night.
Make the Most of Your Stay
The beauty of Charlottesville is how much it offers in a small, walkable city—with a balance of history, art, wine country, and friendly faces. At The Inn at 400 West High, we’re here to help you enjoy it all with local recommendations, cozy accommodations, and personal hospitality.
Planning your weekend getaway? Book your room today and experience Charlottesville in style and comfort.
