Ultimate Weekend Getaway: Virginia's Eastern Shore Itinerary with Kayaks, Wineries & Sunsets
Virginia's stunning Eastern Shore captivates with its fresh oysters, thrilling outdoor adventures, and pristine landscapes. Flanked by the Chesapeake Bay to the west and the Atlantic Ocean to the east, this 70-mile peninsula delivers authentic coastal bliss without the crowds.
—TRIP PLANNING OVERVIEW—
Stay at: Sunset Beach Resort Hotel in Cape Charles (from $99/night off-season, $149 peak) or Waterside Inn in Chincoteague (from $90/night off-season, $165 peak).
Just across the Chesapeake Bay Bridge-Tunnel, Sunset Beach Resort Hotel in Cape Charles offers diverse options: hotel rooms, RV/camping sites, and multi-bedroom cottages. Pet-friendly with an on-site Jackspot Bar & Grill, it features a private beach for Bay sunsets, watersports rentals, two pools, and a lobby store for beach essentials like sunscreen and s'mores kits.
On Chincoteague Island, Waterside Inn is steps from downtown with free lobby breakfast, an outdoor pool, and a pier for cookouts amid iconic Eastern Shore sunsets.
Suggested Prior Reservations: Paddle Your Glass Off Tour with SouthEast Expeditions, Sunset Beach Resort, The Shanty, Onancock Sailing Adventures, Waterside Inn, Refuge Trek at Chincoteague National Wildlife Refuge
—FRIDAY—
Kick off north of Cape Charles with the Paddle Your Glass Off Tour by SouthEast Expeditions to Chatham Vineyards. Launch from Nassawadox Creek, paddle to Church Creek, and gain insights into the ecosystem, wildlife, history, and local watermen's lives.
After a 45-minute paddle, arrive at Chatham Vineyards' 1818 federal-style estate. Greeted by resident Labs Otis and Tucker, enjoy tastings of unique wines like steel/oak Chardonnay, Rosé, Merlot, Cabernet Franc, and Vintner’s Blend—infused with minerality from oyster shell-rich terroir.
Savor your favorite pour before paddling back and driving to Cape Charles for lunch at Deadrise Pies. Their wood-fired pizzas use local, organic ingredients; start with Fried Mozzarella or House Meatballs, then share the DR Margherita (garlic crust, fresh mozzarella) or Gondola (salami, prosciutto).
Stroll walkable downtown along Mason Avenue to Cape Charles Distillery, the Shore's first. Taste whiskeys, bourbon, moonshines, vodka, or cocktails with local fruits/herbs—try maple whiskey or apple pie moonshine.
Next, cool off at Brown Dog Ice Cream with flavors like blueberry or malt milk balls—grab extra napkins for generous scoops.
Nearby, Buskey Cider on the Bay offers flights of unique ciders like Watermelon Rosemary or My Pear Lady (local pears/apples) on their patio.
Drive to The Shanty for dinner: waterfront seafood with Bay views, crab cakes, blackened fish tacos, and creative cocktails.
Check into Sunset Beach Resort, watch sunset from the private beach, and sip Jackspot cocktails.
—SATURDAY—
Enjoy breakfast at historic Cape Charles Coffee House: specialty coffees, French toast, waffles, or yogurt parfaits.
Shop downtown: Voiajer for fair-trade décor/clothing; Moonrise Jewelry for Eastern Shore-inspired 'fish leather' pieces.
Snap a photo at Cape Charles’ beachfront LOVEwork.
At Cape Charles Brewing Company, sample 10+ craft beers (IPAs to coffee ales); check for Breathe Easy and Smile Yoga pop-ups.
Their local-sourced menu pairs perfectly before heading to Onancock (45 min north).
Book Onancock Sailing Adventures ($45/person) for custom Bay tours with Capt. Tom Bunino.
Continue to Chincoteague's Black Narrows Brewing Company: unique local-ingredient beers like Salts Tart Oyster Wheat; supports community causes.
Check into Waterside Inn, then dine at Woody’s Beach BBQ food truck: pulled pork like Big Hot Woody.
End with Island Creamery ice cream (TripAdvisor's Best in America 2014).
Sunset at Chincoteague’s LOVEwork.
—SUNDAY—
Breakfast at Bill’s Seafood & Steaks: granola, omelets, or The Sportsman platter.
Explore Chincoteague National Wildlife Refuge: book Refuge Trek bus tour or hike to Assateague Lighthouse; spot ponies, plovers, squirrels.
Lunch at Pico Taqueria food truck: innovative tacos like Eastside or Maddox with local lemonade.
More Trip Ideas:
- Guide to Loudoun County
- Guide to Harrisonburg
- Guide to Richmond
- Guide to Nelson County
- Guide to Farmville
- Guide to Roanoke
