I Asked Our AI-Travel Planner For a Weekend Adventure in Charlottesville – Here’s What It Created

Mountains calling? Must you go? Same. 

As an East Coaster, I’m partial to the Blue Ridge Mountains (size isn’t everything, okay!?). And one of my favorite ways to experience those scenic peaks is a trip to Charlottesville, Virginia, with its endless hikes, dozens of wineries, and charming downtown. 

To freshen up my next trip up the Parkway, I asked Only In Your State’s award-winning Dashboard AI planner for a little help with the itinerary. The Dashboard works by asking you some questions about your trip—like when you’re going, who you’re going with, and what you like to do when you travel—and then spits out some personalized suggestions, inspired by places Only In Your State writers have visited and loved. 

Where does it have me going in Charlottesville? Let’s find out. 

Where to stay

The idea behind the Dashboard is to take some of the decision fatigue out of your travel planning. But when it suggests three equally charming places to stay, it can present a new kind of dilemma (but the best kind to have, of course).

The most luxe of the Dashboard’s recs is Keswick Hall, a luxury resort featuring a spa, a golf course, fine dining, and a truly stunning infinity pool. (It reminded our writer of an Italian villa when she stayed there.) 

Next up, there’s the Oakhurst Inn, a boutique hotel situated right next to the University of Virginia campus that blends the building’s century-long history with modern amenities (like a pool and mouthwatering breakfast options). 

For a slightly more rustic, but still incredibly charming option, the Dashboard recommends Bailey’s Retreat, a mountainside getaway featuring quaint cabins and cottages on acres and acres of land. 

What to do

The best thing to do in the Charlottesville area is to experience the mountains, and the Dashboard recommends I do just that, both in Shenandoah National Park and along the Blue Ridge Parkway. One hike it suggested that I’d love to try (but am slightly intimidated by): The Blue Ridge Tunnel, which involves passing through a 4,700-foot tunnel right through a mountain. 

After working up a sweat from all that hiking, I’ve got two options for cooling off. I could go for the farm-to-glass brewery and winery experience at Mount Ida Reserve, or get an apple cider slushy at Carter Mountain Orchard. (Or I could do both? I’m thinking both.)

What to eat

When it came to dining suggestions in Charlottesville, the Dashboard outdid itself. For coffee and breakfast, I’ll start at MarieBette Café and Bakery, which our writer says boasts French pastries that are the real deal. 

For a casual lunch, I’ll hit either Citizen Burger Bar, or get some authentic Mexican food at Taqueria El Comalito. Dinner might be a tough choice between two acclaimed Italian restaurants: Lampo Neopolitan for pizza, or Tavola for rustic Italian cuisine. 

The verdict 

It’s a good sign that this itinerary made me even more excited for the next time I get to visit Charlottesville. Well done, Dashboard. Need help planning an upcoming trip—or just want to do some travel fantasizing? Check out the Dashboard and see what it can come up with for you.