Virginia is for Lovers
Virginia really is for lovers. From the Blue Ridge Mountains to the Atlantic Ocean—and all the charming towns in between—there’s something incredibly romantic about this state I’ve called home for many years. If you’re dreaming up a weeklong getaway that’s full of beauty, history, and just the right amount of wine and adventure, here’s how I’d recommend experiencing Virginia in seven unforgettable days.
Start in Richmond: The Capital of Culture & Cocktails
Kick things off in Richmond, the historic heart of Virginia. I always suggest checking into a classic boutique stay like Linden Row Inn—it’s walkable to so much downtown. For dinner, head to Max’s on Broad for elevated French fare, then make your way into Richmond’s buzzing brewery scene. You can’t go wrong starting with Hardywood and Triple Crossing—two staples that set the tone for the craft beer movement here. Then wander through Scott’s Addition, a neighborhood filled with taprooms, cideries, and local flavor.
As the night sets in, hit Shockoe Bottom and the 17th Street Market area for a little nightlife. Whether you land at Rosie Connolly’s for a pint or Havana 59 for a rooftop mojito, the energy is always high and the vibes are always good.
And if you love a little history with your adventure, don’t skip The Valentine Museum, the Virginia Museum of History and Culture, or a stop at St. John’s Church, where you can catch a reenactment of Patrick Henry’s legendary “Liberty or Death” speech.
Slip into Small Town Charm: Culpeper
From Richmond, head north to Culpeper—a picture-perfect example of small-town Virginia. I like to stay at the Culpeper Center Suites and always make time for dinner at Flavor on Main. Everything is walkable here, including a cozy little brewery and a handful of bars. And if you’re into dive bars with stories, stop by Davis Street Pier—it never fails to entertain.
Hit the Trail in Shenandoah
Next up: nature. Just 45 minutes from Culpeper is one of my favorite hikes in the state—Old Rag Mountain. It’s a full-day kind of hike, so pack a picnic (and maybe a bottle of Virginia wine). The summit views are more than worth the climb, and it’s an unforgettable date-day adventure.
Wine & Wellness in Charlottesville
After your mountain escape, head south to Charlottesville and check into the iconic Boar’s Head Inn. This is where you unwind. Book a spa treatment for the morning and grab a healthy breakfast to fuel your next stop: the vineyards.
Virginia wine is no joke—some of the best in the world, and yes, I said that. I recommend a trio of wineries for your Charlottesville day:
Early Mountain (for design, quality, and serious wine game)
Barboursville Vineyards (for history and ambiance)
King Family Vineyards (for stunning views and top-tier reds)
All three make for a perfect loop, and by day’s end, you’ll be ready to return to Boar’s Head for a second night.
End at the Coast: Virginia Beach
To wrap up the week, drive east until you reach the edge of the map—Virginia Beach. Book a stay at The Cavalier Hotel, which has been beautifully renovated and is just a short stroll to the oceanfront. Spend the day on the sand, walk hand-in-hand along the boardwalk, and cap it off with seafood and a classic Crush cocktail at Waterman’s. It’s the kind of place where the sunset hits different and you’re reminded just how magical this state really is.
Whether you're a Virginia local looking to explore your own backyard, or visiting from out of state and searching for the perfect mix of romance, adventure, and relaxation—this itinerary has you covered.
Need ideas for what to pack or which vineyard to hit first?
I’ve got you. Until next time, happy travels.