Come for the Sailor-Friendly Vibe, Stay for the Cape Charles Sunset
If you’re a racing sailor, you may know Cape Charles as the destination you race to once a year from Hampton, have a party, and race back the next day for the annual Leo Wardrup Memorial Cape Charles Cup. If you’re a cruising sailor, you may know Cape Charles as one of the few places in the area with a fuel dock! No matter your sailing preference, you may know the place for its irresistible photographer’s magnet: the “Love” statue on the beach.
Whatever reason brings you to the southernmost town on the Eastern Shore, the once-bustling 1880s railroad town that fell asleep and recently reawakened offers plenty to keep visiting sailors entertained, well-fueled, well-fed, and coming back for more. Cape Charles is located near the tip of the DelMarVa Peninsula and the eastern entrance to the Chesapeake Bay. The town’s historic buildings house bed and breakfasts, restaurants, shops, and an old-fashioned soda fountain. Here you may enjoy beautiful sunsets, scenic marinas, and a sandy public beach.
Before Chesapeake sailors Kristin Rutkowski and her husband Seth bought a home in Cape Charles in 2022, they’d spent some time there. Kristin, who’s the author of the photography book “Her Helm,” says, “I’d been visiting Cape Charles for years on photo trips with a group of photography friends, in spring and fall, exploring the area, the water, the farms, the towns.”
What does she wish more people knew about Cape Charles? “That it’s there, and it’s welcoming! We do get a few visiting sailors, even international ones.” She recounts walking along the docks and meeting a cruising couple from New Zealand who were sailing around the world.
For sailors who like a local’s recommendation, here are some of Kristin’s favorite places when she gets back to Cape Charles:
- Northhampton Hotel in front of the town beach, a big white building with a wraparound porch, for brunch.
- Delicious sandwiches and European-style baguettes at the Mason Avenue Bakery.
- The Shanty for sunset cocktails overlooking the Bay. “The sunsets are amazing!”
- The Almeta, coffee shop.
- Coastal Baking Company.
- Hook @ Harvey Bistro.
- Deadrise Italian Kitchen for pizza.
- Two taco trucks in Cheritan (three or four miles away): El Ranchito Mexican Store and Carmelitas.
- Festivals in the park, concerts in summer.
- Cape Charles Public Beach.
- Cape Charles Museum and Welcome Center.
- Mini golf on the way out of town.
- Kiptopeke State Park.
- Magothy Bay State Natural Park Area for nature walks in the woods and out into the marsh (15 minutes south).
- For visiting cruisers, the Cape Charles Memorial Library, right in town.
Kristin says, “The nature trails are great. There’s a birding group in Cape Charles called Birding Eastern Shore—they share events, nature walks, and more. They are keen on helping to support research and science about ospreys and more.”
She gives away one of her photography secrets: “The sunrises in Oyster, on the seaside of the Eastern Shore, are exceptional.” (Oyster is a 12-minute drive from Cape Charles.)
Tall ships are coming!
As part of America’s 250th birthday celebration, Cape Charles will host Sail Virginia 2026 and welcome majestic tall ships to SailFest Cape Charles on June 19-21, 2026. Featured vessels include Kalmar Nyckel, Lynx, and AJ Meerwald.
These historic vessels, along with beautifully restored Chesapeake Bay Oyster Buy Boats and Coast Guard and Navy vessels will give visitors a rare glimpse into the maritime heritage of Viriginia’s Eastern Shore. Explore the towering masts, intricate rigging, and decks that have sailed the seas. Meet the crews, hear their stories, and experience the seafaring traditions that helped shape our nation.
SailFest Cape Charles will feature free ship tours of our visiting historic sailing vessels, period re-enactors, presentations by local historians, hands-on activities for kids, fife and drum corps, a Saturday evening concert featuring Three Sheets to the Wind, a local artisan vendors market, food, fireworks, and fun! Learn more at sailfestcapecharles.com.
Community Sailing in Cape Charles
Cape Charles Sailing, also known as Cape Charles Community Sailing, was founded by Hannah Twiddy and Mia Guinan in 2019 during a sail across the Chesapeake Bay, inspired by the idea that a grassroots sailing camp could provide kids on the Eastern Shore with a new way to experience the water. Since then, the organization has expanded to host multi-week summer camps that include volunteer and counselor-in-training programs. Cape Charles Sailing offers adult sailing courses, hosts events and regattas, and collaborates with local organizations across the Eastern Shore, Hampton Roads, and northeast North Carolina to provide scholarships and programs that make sailing accessible to all. Learn more at: capecharlessailing.com/about.
Getting there
Driving to Cape Charles from Annapolis by land yacht, with no bridge traffic, will take you four hours.
Driving to Cape Charles from Hampton will take you almost an hour and a half, depending on bridge traffic.
Arriving by boat, there are a few marinas in town and north of town. The Cape Charles Marina is easily accessible, especially for deep-draft boats, and walkable to town, as is the Cape Charles Yacht Center.
Arriving by race boat: This year’s LWM Cape Charles Cup (August 16-17) Saturday night event will take place on an open grassy area off Mason Avenue between the Cape Charles Town Docks and Gull Hummock Gourmet Market.
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