When you're in need of a break from the hustle and bustle of a busy city, be prepared to take a trip to Charlottesville, Virginia. Unassuming and totally rich in history, Charlottesville is brimming with Southern charm and wine—lots of wine. And must-try restaurants. Here to show us around her city is lifestyle and travel influencer Alicia Tenise. Keep reading for Alicia's guide to living your best life in what National Geographic Traveler considers one of the US's best small cities.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

Downtown Mall

I grew up in the D.C. suburbs, but moved to Charlottesville about eight months ago with my boyfriend. I visited regularly for a year before making the move.

I like to describe the vibe in Charlottesville as “Southern-Lite.” Central Virginia is where you finally start feeling like you’re truly in the South: everyone is incredibly polite and friendly, but very laid back. 

Charlottesville is truly a hidden gem. For starters, it’s Thomas Jefferson’s hometown, and you see a lot of TJ’s influence wherever you go, and the town is rich full of history. 

Charlottesville is also the heart of Virginia Wine Country (Thomas Jefferson was also the first person to attempt to grow grapes in Virginia!), and there are 33 wineries that are a part of the Monticello Wine Trail. Wine tasting is an absolute must when you’re in Charlottesville.

Lastly, Charlottesville is tucked into the Blue Ridge Mountains, and there are a lot of incredible hikes and trails you can explore in the area. Drive along the famous Blue Ridge Parkway, or you just enjoy the mountain views from a nearby winery. 

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

Best Time to Visit

October is Virginia Wine Month and that’s right around our harvest season, and the weather is usually the most comfortable at that point. However, anytime between April-October is good—just prepare for the heat if you come during the summer.

Where to Stay

The Graduate is super cute and right near UVA. I haven’t stayed at The Townsman yet but I’ve heard good things. Quirk Hotel is opening their second location in Charlottesville in the next few months, and I’d definitely be on the lookout for them – their Richmond location is incredible.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI


Dressing the Part

It really depends on the season. Summers are very hot and humid, and our winters are somewhat mild, but we can occasionally get a few cold snaps. If you’re going wine tasting, avoid an all-white outfit            

Getting Around

If you’re going to the wineries, either hire a private driver or go on a group wine tour. I would not recommend taking an Uber/Lyft out to the wineries: since the wineries are located in more rural areas, it’s difficult to get a signal and there also isn’t a lot of traffic nearby. It’s easy to get yourself out to the winery, but I’ve seen some people get stranded when trying to call a car to get back to town!

Aside from that, having a car is nice if you want to venture out to the mountains to explore, but you can definitely take Uber or Lyft anywhere else you need to go that’s in town.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

Tip for First-Timers 

Charlottesville is also home to the University of Virginia, and I’d try to avoid visiting during graduation weekends – it will be a madhouse, and hotel/Airbnb prices will skyrocket! 

Charlottesville has 22.8 restaurants per 10,000 people, and we currently rank 14th in the country for restaurants per capita, so it’s a city that’s perfect for foodies!


Don't leave without a bottle of Virginia wine, of course! We’re known for our Cabernet Franc, Chardonnay and Viognier.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

Graduate Hotel


11AM Breakfast at Bodo’s Bagels, the most popular breakfast spot in town. They serve New York-style bagels that are made fresh daily.

12PM A fun tourist-y activity would be walking on the grounds of University of Virginia (a piece of the Berlin Wall is here, rare books at the library, see the classic, Thomas Jefferson-era architecture).

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

Ace Biscuit & Barbecue

2PM Grab lunch at Tilman’s, a super cute wine and cheese shop with wines from all over the world, they have great sandwiches and salads too!

4PM Go shopping in the Downtown Mall Boutiques. Darling Boutique is a great consignment shop, Jean Theory has amazing premium denim and Rock Paper Scissors is a cute stationary shop.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI


8PM Petit Pois for dinner because they have great French food, or Prime 109, an upscale steakhouse.

10PM Alley Light is the best cocktail bar by far). I also like Commonwealth Skybar (fun rooftop bar) ad The Whiskey Jar (laid back bar with live music).

insiders guide to charlottesvile virginia Alicia Tenise OUAI


10AM Breakfast at Ace Biscuit.

12:30PM Wine tasting (I’d recommend 3 wineries/day): Stinson Vineyards, King Family Vineyards, Pollak Vineyards would be my route of choice. Stinson is a cute boutique winery, King is arguably the most popular winery in the region and has polo matches on Sundays in the summer, and Pollak has a wide selection of wines. Heads up, wine tasting will take at least six hours.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

King Family Vineyards Polo Match

3PM Lunch at Greenwood Gourmet Grocery—pick up sandwiches and snacks in between King & Pollak Vineyards

5PM For a museum-like experience head to Monticello (Thomas Jefferson’s house) and president James Monroe’s Highland.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

7PM Dinner at Tavola. It's one of the best Italian spots in town. The linguine alla carbonara is my go-to!

9PM Cicchetti Bar is right next door to Tavola, and they serve incredible craft cocktails.

insider's guide to Charlottesville Virginia Alicia Tenise OUAI

Photos by Tom McGovern

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