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From our partners at The Scout Guide, they have curated the ultimate Virginia road trip itinerary that highlights six charming cities, each offering its own unique blend of local culture, hidden gems, and unforgettable experiences.
Looking for the ultimate Virginia road trip guide? Whether you’re craving mountain views, salt-air escapes, or boutique-filled streets, there’s no need to venture far. We’ve rounded up a dream-worthy lineup of Virginia destinations—each one a beloved TSG city—offering insider access to the best in local shopping, dining, culture, and hospitality. From the Blue Ridge to the bay, this in-state road trip is a stylish and soulful way to experience the beauty of the Commonwealth.
Image courtesy of Aaron Watson Photography.
CHARLOTTESVILLE, VIRGINIA
Why visit the dynamic university town of Charlottesville, Virginia? Antje Lemoine, editor of The Scout Guide Charlottesville, can name a few reasons. This bustling and bucolic city offers mountain views, top-unique boutiques, historical sites, and a busting food and wine scene. Get insider scoop on Cville by checking out their Insider Guides and follow along on Instagram to stay up to date on all of the happening.
Editor Sarah Phillips (right) of The Scout Guide Alexandria. Photo courtesy The Scout Guide Alexandria.
ALEXANDRIA, VIRGINIA
History, proximity, community—these are just some of the traits that make Alexandria, Virginia, an idyllic destination. Stroll down charming King Street in Old Town Alexandria and you can feel the ghosts of the Founding Fathers who once frequented the area while surrounded by more than 200 locally owned shops, restaurants, and businesses. The Scout Guide Alexandria editor/owner Sarah Phillips is passionate about recommending where to stay, sightsee, sip, and more during a trip to her town. Get insider scoop on Alexandria by checking out her Insider Guides. And follow along on Instagram to stay in the know of local happenings.
Shagbark Restaurant in Richmond, Virginia. Photo courtesy of Shagbark.
RICHMOND, VIRGINIA
A revitalized city brimming with fashionable boutiques, award-winning restaurants, a thriving arts scene, Richmond has rightfully earned its spot on the map as a hip Southern city that is worth a weekend visit. A Virginia girl through and through, The Scout Guide Richmond editor/owner Cheney Edmunds grew up in Norfolk and visited Richmond often during her school days at Randolph-Macon College. After moving back to the area seven years ago, Cheney was overcome with excitement seeing a new and improved Richmond. Discover all Richmond has to offer by perusing Cheney’s Insider Guides and follow along on Instagram.
The Scout Guide Tidewater editor Mary Kaufman. Photography by Andi & Zoe.
TIDEWATER REGION, VIRGINIA
A quintessential East Coast beach town, Virginia Beach boasts one of America’s most photogenic boardwalks, plenty of waterside oyster bars, and an abundance of unique, high-end shopping opportunities. But what many might not know is that the well-known waterfront destination also neighbors the bustling city of Norfolk, and is surrounded by many charming “sister cities” nestled into the beautiful coastal plains. The area, known to locals as the Tidewater Region, is steeped in history and military lore, and surrounded by water. The Scout Guide Tidewater editor Mary Kaufman always encourages visitors to tack on an extra day or two to their Virginia Beach travel plans to discover all the area has to offer. Check out her Insider Guides before heading out. And don’t forget to follow along on Instagram.
Merchant’s Square in Williamsburg. Photo courtesy TSG Williamsburg and The Chesapeake Bay.
WILLIAMSBURG & THE CHESAPEAKE BAY, VIRGINIA
Colonial Williamsburg is one of the historic landmarks everyone needs to visit in their lifetime. This site is best known as a meticulously restored colonial village, but what many visitors might not realize is it’s adjacent to some of the most picturesque waterfront communities on the East Coast, with endless waterways worth exploring. To help those traveling to Williamsburg make the most of their time in the area, The Scout Guide Williamsburg & The Chesapeake Bay editor/owner Sara Harris to shares her Insider Guides to the area. Follow along on Instagram for all the scoop on local businesses in the area.
Beautiful Hunt Country.
HUNT COUNTRY, VIRGINIA
And of course, we couldn’t leave out our beloved Hunt Country. Just a short drive from D.C., our picturesque region is ideal for weekend escapes—whether you’re soaking up the summer sun, savoring fall foliage, or cozying up in the quieter seasons. Here, you’ll find incredible food, sweeping scenery, and no shortage of horses. Explore it all with our Insider Guides and follow along on Instagram for the latest local favorites. We can’t wait to welcome you.
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