Where: Richmond, Virginia
What to do: Mixing Southern charm with the energy of a college town and plenty of old-school attractions, Richmond is one of our fave spots for unearthing treasures old and new. Hit up Carytown for adorable boutiques, take a stroll down Monument Avenue, or plan your trip around one of the city's wine festivals to taste some of the region's best vintages. We suggest taking a walk through Lewis Ginter Botanical Garden, then checking out the shops on Cary Street (especially Need Supply, our favorite), before settling in for a cozy dinner at Can Can Brasserie.
What to wear: A simple dress and walkable ankle boots can take you from strolling between shops to a casual dinner, and a roomy tote will let you stash everything from a bottle of wine to your great new jewelry finds.
Melissa Odabash Jamie Striped Stretch-Jersey Mini Dress, $230, available at Net-a-Porter; 3.1 Phillip Lim Camp Jacket, $650, available at La Garconne; Rag & Bone Mid Moto Boots, $535, available at ShopBop; H&M Necklace, $17.95, available at H&M; Zara Shopper with Clasp Frame, $99.90, available at Zara.
Photo: Via Richmond Metropolitan Convention & Visitors Bureau