How to Plan Your Charlottesville Destination Wedding

In 2019 I worked with a lot of couples who chose the foothills of the Blue Ridge Mountains for their destination wedding. Chris and Alessandra were in that category. Both are in the Navy and are currently stationed in California. As is the case sometimes with military couples, they had gotten legally married a year earlier to be stationed together and had welcomed a baby girl during that first year of marriage, but had never had a true wedding.

They chose Charlottesville as their base for their celebration because it was halfway between their families on the east coast and planned a full weekend of festivities for friends and family who flew in from all over the world for their wedding. 

The weekend began with a family-reunion style picnic at Carter’s Mountain Orchard followed by the rehearsal and dinner. The next day they got ready in downtown Charlottesville at 200 South Street Inn before heading over to their venue at James Monroe’s Highlands (just south of Charlottesville) for the ceremony and reception. The weekend ended with a brunch for anyone who was still in town. 

By the time they got married, Chris and Alessandra and been together for seven years and had traveled extensively together. At the pre-wedding picnic, Alessandra displayed photos of their travels and adventures in beautiful scrapbook-style collages that made me take a serious look at how I’m printing and documenting my own memories. 

One of the most fun parts of their wedding was seeing them get to introduce their young daughter to their friends and family. They aren’t posting photos of her online — which I get, I’ve made the same choice for my daughter — so you won’t see their kiddo in this blog, but capturing family coming together is probably my favorite thing about wedding days — or weekends in this case. 

Of course, planning a destination wedding — anywhere — can be a little stressful. Since I’ve worked with a lot of couples who come to the mountains and valleys of the Blue Ridge from elsewhere to get married, I’ve collected some tips worth pondering for your destination wedding. Here are some of them:

Rent a Space to Congregate 

Some venues offer houses or manors to get ready in — use them and stay for the weekend. Renting a large space in which your bridal party and/or family can congregate makes getting ready a lot more fun and relaxed – especially when the people you have invited to that space are those you love but don’t get to see often. 

If your venue doesn’t offer this kind of space, other options include renting one large home or several spaces in close proximity to each other from a vacation rental company, such as VRBO or Airbnb, plus checking out the possibilities with nearby inns or hotels like Chris and Alessandra did.

Couples who do this are often able to carve out some time to hang out and sit around the fire with their friends and family outside of the craziness of the wedding day itself. 

Choose Vendors Carefully

When possible, come in person well before the date of your wedding to meet with vendors, do a cake and menu tasting, and chat with your photographer and DJ to make sure you click. But if coming in person isn’t feasible, then make sure you are choosing local vendors with lots of reviews (so you can get an idea of what other people’s experiences were like). You want to make sure the vendors proved to be responsive and to know the area well. Of course, a highly rated vendor can be a good source for recommendations for other high quality vendors. 

I view responsiveness as a key testing point in this industry. Most wedding businesses are small, with at most a handful of employees. Many business owners are like me – we mostly do it all ourselves, hiring temporary help as needed. But during business hours (i.e., not counting holidays, weekends and evenings), you should get a response to questions and inquiries within 24 hours. If you don’t, move on. There are a LOT of vendors in the Blue Ridge region and when planning a destination wedding in particular, knowing you can count on your vendors to respond and be helpful makes the process so much less stressful. 

Make a Weekend Out of It

The mountains, foothills and valleys of the Blue Ridge are peppered with cute little towns with great restaurants, an unexpected plethora of vineyards and craft breweries, and amazing hiking, including that in Shenandoah National Park. As a result, there are a ton of options to hang out with your guests or bridal party before and after your wedding if you choose. 

 Ideas:

1. Go wine or beer tasting. Here is a list of all the vineyards and breweries in Virginia.

2. Visit Luray Caverns, the largest caverns in the eastern United States. Or, for smaller and less commercial cave viewing, try Shenandoah Caverns or Skyline Caverns. 

3. Spend a day on the James River tubing, canoeing or kayaking. 

4. Catch a free outdoor concert at Charlottesville’s Sprint Pavilion every summer Friday or check out the community-oriented, nonprofit (free) IX Art Park, which features local art and music throughout the warm months. And while you’re in the downtown area, stroll along the walking mall, eating ice cream, exploring local restaurants and window shopping the boutiques. 

5. Explore local history and take a tour of Monticello, James Monroe’s Highlands (also a cute wedding venue!) or Montpelier. 

6. See the Blue Ridge Mountains from the air and schedule a hot air balloon ride (or skydive for the adventure junkies). This hot air balloon company also offers tethered rides for events.

Of course, if you’d rather hang out with just you and your person and choose to relax in this beautiful region for your honeymoon, these are also great ideas for what to do with your time.