Cape Charles, perched at the edge of Virginia’s Eastern Shore, feels like a throwback to the kind of beach town that existed before chain stores and crowds. It’s walkable, waterfront, and wonderfully unhurried—just the kind of place where a single day can feel like a full reset. If you’re heading that way, here’s how to do it right.
Morning
Start your day on Cape Charles Public Beach, where the sun rises quietly over the Chesapeake Bay and the water laps gently at the shore. The beach is free, open year-round, and known for its shallow, family-friendly surf. A short walk along the adjacent fishing pier adds a little stretch to your morning and offers a peaceful view of the town just waking up. From there, wander over to Cape Charles Coffee House, a local go-to tucked inside a restored 1910 bank. The creaky floors and pressed-tin ceilings are pure Eastern Shore, and the menu—crab-cake Benedict, cinnamon-swirl French toast, and proper espresso—sets you up right for the day.
After breakfast, head to the water again with SouthEast Expeditions, who’ll deliver a kayak or paddleboard directly to the beach so you can launch within minutes. If you’re feeling ambitious, sign up for their popular “Paddle-Your-Glass-Off” winery tour, which ends with a guided tasting and a well-earned glass of local wine. Before the sun climbs too high, make a quick trip to the Cape Charles Natural Area Preserve, where a shady 0.9-mile boardwalk trail winds through maritime forest to a scenic overlook. Keep an eye out for osprey and the elusive Northeastern beach tiger beetle—this quiet corner of the peninsula is a biodiversity gem.
Afternoon
When the midday heat kicks in, lunch at The Shanty hits the spot. This dockside seafood joint serves up soft-shell crab sandwiches, fish tacos, and cold drinks beneath colorful umbrellas overlooking the marina. It’s relaxed, breezy, and close enough to town that you can stroll back to Mason Avenue afterward. Spend some time exploring Cape Charles’ main strip, lined with indie boutiques and art galleries that reflect the town’s creative spirit. Don’t miss Brown Dog Ice Cream, where small-batch scoops made from local ingredients help beat the heat (favorites like honey lavender and lemon curd don’t last long).
Afternoons offer a choose-your-own-adventure vibe. If you’re up for more nature, head to Kiptopeke State Park just south of town. There’s an unguarded beach for swimming, a long fishing pier, and hiking trails that lead to views of WWII-era concrete ship breakwaters anchored in the bay. If golf is more your pace, Bay Creek Golf Club offers two signature courses—one designed by Jack Nicklaus, the other by Arnold Palmer. You’ll need to book ahead through the resort or with a lodging package, but the views and course conditions are worth the planning. If you’d rather stay in town, slide into a shaded seat at Cape Charles Brewing Company for a flight of local beers and a seafood burger. The brewery has a relaxed patio and stays open straight through to dinner.
Evening
As the golden hour sets in, head to the harbor for a sunset sail with SeaEO Luxury Charters. Their 90-minute cruises run nightly through October, offering peaceful views of the bay as the sky turns gold and pink. You can opt for a private charter or add a charcuterie board if you want to elevate the experience—either way, it’s a serene way to end the day on the water.
Back on shore, Cape Charles delivers on dinner with options to match your mood. For an upscale meal, book a table at Hook @ Harvey, an elegant bistro tucked inside the yacht center, where local scallops and glasses of champagne are served with full views of the waterfront. It’s open Tuesday through Saturday, and reservations are a must. If you prefer a more casual vibe, Oyster Farm Seafood Eatery offers classic crab cakes, a raw bar, and plenty of open-air seating right on the marina. The water views stretch wide, and the atmosphere is easygoing even on busy nights.
Close things out with a nightcap at Cape Charles Distillery, where small-batch bourbon and moonshine cocktails are poured in a newly expanded Mason Avenue space. In addition to the main bar, you’ll find the Salty Rooster eatery and a rooftop deck, making it a great last stop before calling it a night.
