One of the great things about a road trip is that you are truly at liberty to overpack. Eight days definitely means three rompers, two dresses, two pairs of shorts for five shirts, plus all the underwear to accommodate varying outfits, and at least three pairs of shoes. Driving through wine country requires its own special necessities—you’ll need to prepare for take-home bottles and varying occasions of dress. I don’t make the rules. 

The beauty of a road trip is your ability to endlessly add to your repository (your car) as you go along, but I’m sure you’d rather spend your time sipping a Petit Manseng among the lush Blue Ridge Mountain vineyards than picking up forgotten wares at a Dicks Sporting Goods (like this ostensibly expert travel writer). 

If you want to avoid suburban strip malls at all costs, you’ll want to make sure you bring along everything listed out below. Cheers! 

How to plan the perfect road trip→ 

Packing Cubes 

Unless you’re Marry Poppins, eight days of clothes in one Weekender would be a nightmare without Packing Cubes. I separated mine into dresses/rompers + bottoms, tops, and socks/underwear. Bonus: the Away laundry bag that comes with all the suitcases is a nifty thing to bring along as well. 

Wine Cooler 

You need something to store all the delicious wines you will inevitably purchase after tastings. How will you remember anything you’ve learned from those long-winded sommeliers without some souvenirs? You could be fancy and splurge on a Yeti Cooler to protect your bottles from overheating in the car, but I found this Igloo brand soft cooler insulated my wine from the elements enough to get me from one place to the next and was super easy to transport. 

All Killer No Filler Playlist 

Just before I hit the road, my mother shared a collection of 70s female folk artists she loves, Taylor Swift had recently released cardigan, and Cardi B and Megan Thee Stallion graced our ears with the singular yet no less seminal track “WAP.” I had to find a way to make all of these wonderful female musicians operate in one playlist so that I wasn’t diddling with Spotify while driving, and I am happy to report that (I believe) I accomplished this. You’re welcome, world. 

Toiletries 

I went pretty bare bones for this trip. Make up-wise, I stuck to some undereye concealer and mascara, Make Up Forever and Clinique respectively—the same brands I’ve been using for the better part of a decade. I love my Boie toothbrush because it’s antimicrobial, meaning it can handle being in your travel case for the long haul without getting gross. I use Bite Toothpaste bits, which I keep in a pill organizer separated from my prescriptions. 

I’m also happy to report that I’ve found a natural deodorant that I like, courtesy of Package Free Shop. And this one’s for the people with menstrual cycles: I have found my holy grail menstrual cup, the Lumma, and I don’t know what I would have done without it on this trip. I don’t know about you, but changing a tampon in a gas station bathroom every few hours doesn’t exactly appeal.

Moleskin Journal

I’m one of those impossible people with a rigid morning routine, and it includes journaling, especially when I travel. I’ve been using Moleskins for years and never had a reason to try anything else. Don’t fix what ain’t broke, ya know?

Chacos Sandals  

I’m convinced that Chacos are the perfect summer shoe. I could easily hike through rugged vineyard trails as well as take them on a stand-up paddle boarding adventure on the James River. Yet, they pair well with summer dresses in a casual-cool kind of way. The fun lavender color I got certainly helps with that. 

Towel

I didn’t go to the beach, but these quick-dry, sand-free towels from Sand Cloud are super absorbent and came in handy after dips in the river.

Bags in Bags 

Overpacking does come with its disadvantages, but I combat this with a kind of Russian doll effect for the multiple bags needed (from totes to going-out purses). I love this leopard Baggu tote, which my leather OAD crossbody fits right into when transporting from vehicle to hotel room.

Disposable Camera 

Disposable cameras are a godsend for people who are not gifted photographers (ahem). They give an appealing vintage quality to any photo you take and they pick up colors well. My tips: They’re best for landscapes or a depth of field of about 4-6 feet (don’t try to do close ups; they’ll blur) and they really like a lot of light, so you’ll need the flash at night or in dim indoor settings.

COVID-19 Preparedness 

I tried to do reusable masks, but after a serious bout of mascne I had to revert to disposable surgical masks. I found these purple masks on Amazon are slightly less depressing. I packed hand sanitizer in every bag I took with me (I love the Public Goods spray bottle sanitizer). More of our COVID-19 travel tips can be found here.