Charlottesville Insider

If you’ve been to Charlottesville and its surrounding areas before, you know that this is one of the most romantic places in the US. We’ve got beautiful mountains nearby, gorgeous grounds around UVA, perfectly set wineries and craft breweries, an amazing pedestrian mall where you can take a romantic stroll, and many other hidden gems for you and your sweetheart to see and be a part of.

But even if you have not been to our lovely city, you may have heard about our amazing restaurants. The stat that we keep hearing is that we have the most restaurants per capita of any US city. The only data on this that we can find is from the Huffington Post a while back saying that we actually rank 14th on that list, but still, that’s a lot to choose from! So, if you are planning to come to or already be in Charlottesville for Valentine’s Day (or any special occasion) and are looking to have a romantic meal, how in the world do you decide where to go?

Never fear. We are here to help. Chances are that no matter where you go, you will have a great time, but there are some restaurants that seem to be a level above in the ‘romantic’ department. We have picked five that fit that bill based on ambiance, customer service, and delicious food, and will be sharing their stories with you on this blog over the next couple of weeks. Our first featured restaurant is Vivace!


Exceptional food. Amazing attention to detail. Friendly and professional service. Charming and romantic setting. This is The Ivy Inn.

Since 1995, Angelo Vangelopoulos and his family have been serving up what they call ‘locally-inspired seasonal cuisine.’ Eat there and you will just call it ‘delicious.’ There is a reason Vangelopoulos has been called the best chef in Charlottesville by his peers. Whether it’s grilled local trout, pomegranate glazed duck breast, or grilled certified angus beef tenderloin, you can tell that the meal you have chosen has been prepared by someone who believes that food should not only taste great, but should be presented elegantly and with love. You feel when a restaurant’s team is passionate about what they serve. And that is what you get from the chef and the staff at the Ivy Inn.



Fleurie is a special restaurant on a side street of the downtown mall in Charlottesville. While it is know throughout the area for its incredible French-inspired cuisine, Fleurie has also been recognized recently as one of the ‘100 Best Wine Restaurants‘ in the nation by Wine Enthusiast magazine. When a quaint restaurant in Cville gets national attention, you know it has to be amazing. The service, the food, the ambiance – everything about Fleurie says elegance and transports you to a different world until you walk back out onto the bricks and realize you are in Charlottesville again. It’s just that good.

On non-holidays, Fleurie not only offers its incredible a la carte menu, with items such as Beef Tenderloin au Poivre and Butter Poached Lobster, but also offers a pre-theatre prix fixe menu available before 6:30, perfect for when you and your date are going to the Paramount or the movies later in the evening.

For Valentine’s Day, however, Fleurie is offering only a Valentine’s menu that you and your sweetheart are sure to love. You can find that menu by scrolling to the bottom of this page:

Wherever you decide to dine this Valentine’s Day in Charlottesville, we hope that you have an incredible day with the one you love (or just like a lot, if it’s early). And if you are visiting and need a place to stay, check out our friends at Stay Charlottesville. They still have availability on and around Valentine’s Day, and you can book by calling 888-977-STAY or online at


“It is so hard to say which of the dining rooms is the most romantic!
I think you have your first date in the bistro, fall in love on the mezzanine, and get engaged and celebrate all of your anniversaries upstairs.”
Dean Maupin, Chef/Proprietor of C&O Restaurant

When you first approach the entrance to C&O, you may think, as I did upon my first visit many years ago, that the structure housing this well-known restaurant, that the building itself, with its beautiful historic bricks, tucked away entrance, and torches lighting the way, exudes romance and mystery and warmth. You just know that there is an amazing dining experience happening beyond that front door and that you have brought your sweetheart to the perfect place for Valentine’s Day or any day you want to be extra special.

Of course, a couple of reasons that C&O made this list are amazing service and awesome food.
The staff is friendly and welcoming, with just the right amount of attentiveness for a couple’s date night. There is an extensive wine list, and the sommelier is more than happy to make suggestions based on your meal choice or your favorite varietal.. For your first visit there, you may also request dinner suggestions from your server. You will find that the staff is very passionate about the food they serve, and their detailed descriptions may make your mouth water. From the Steak Chinoise to the Scottish Salmon, everything is made to perfection. C&O sources their products mostly from local markets and farms, leading to words in reviews like “fresh and delicious.” So, any suggestion is the right suggestion.

As incredible as the food and service is at C&O, it can’t be denied that the ambiance is one of the things that sets this place apart from all the rest. Each dining area (there are six) is charming and seems to have a story to tell. And as long as I have lived in this beautiful city and as many times as I have been to C&O, I have to admit, I have never heard those stories. So, I thought I would go right to the source. I asked Dean Maupin, Chef/Proprietor of C&O Restaurant, if he could share some stories about the history of the building, about which room seems to be the most romantic, and a story about the most memorable table they’ve served.


It would be easy for me to go on for days about the delicious food at Vivace (calamari and chicken marsala to die for), or the amazing welcoming and friendly staff (Jeff, who usually greets you at the door, is more like family by the end of the meal), or the incredible warm feeling you get wherever you are seated (personally fond of anything upstairs). Those are the things that got them on this list. But, instead of me rambling on, I thought it would be great to hear about the restaurant from someone who knows it best, Co-Owner and Manager, Jeff Sobel.