Cape Charles, VA: The Perfect 2-Day Itinerary
Cape Charles is a hidden gem on Virginia's Eastern Shore, with so much charm and natural beauty. This quaint town is special for several reasons, including the calm beaches, small-town charm, and relaxed pace. Lukas, Lenny and I loved our trip there and wanted to share our perfect itinerary with you!
If you'd like to watch my Top Tips for a trip to Cape Charles, you can here:👇
Here is our 2-Day trip to Cape Charles Itinerary:
DAY 1:
9:00am
Arrive at Cape Charles Beachfront (street parking on Bay Ave)
Visit the “Love” sign, it's crafted out of an old tire, oyster shells, a kayak, and crabbing pot.
This beach is PERFECT for babies & kids, as it's shallow and calm. Lenny loved it!
*Also the beach cart we got was SO helpful carrying all of our stuff. The wheels worked great in the sand and made our trip so much easier.
We got it on Amazon here.
11:30am
Cape Charles Historic District: (along Mason Ave)
Optional: Rent Golf Cart: Eastern Shore Custom Carts.
Shops & Stores:
Peach Street Books - 9am-3pm
Moonrise Jewelry - 10am-5pm
The Boardwalk - 10am-6pm
Destination 23310 - 10am-5pm
Lemon Tree Gallery and Studio
Historic Palace Theatre
Cape Charles Candy Company - 11am-6pm
Chuckletown Productions - 9am-7pm
Table and Tonic - gift shop, 10:30am-6pm
Cape Charles Coffee House - 8am-3pm
Drizzles - gourmet grocery store, 10am-5:30pm
K-Coast Surf Shop - 9am-9pm
Like a Sailor - novelty store, 10am-6pm
1pm
Lunch:
Edible Picasso - 10am-6pm, poke bowls, asian noodles & bowls
Brown Dog Ice Cream - 12-9pm (no dairy-free options)
3pm
Check into your hotel or airbnb.
For this trip we stayed at an amazing condo located right downtown! The location was great, but we found the couch and bed uncomfortable.
Here's the link if you'd like to book it on VRBO:👇
5pm
El Sol - 4-11pm, take your margarita to the top floor for a view!
6:30pm
Dinner:
Deadrise Italian Kitchen - 4-9pm, Pizza & pasta
or
Cape Charles Brewing Company - 11:30am-8pm, Burgers & gastropub fare
8:00pm
Sunset at Beach 8:17pm
or
Sunset at The Shanty - 11:30am-9pm, waterfront casual dining
-------------------------------
DAY 2:
Check out of hotel or airbnb.
8am
Breakfast:
Coastal Baking Co - 8am-3pm, coffee & baked goods
*When we went this year with our baby, Lenny (2026) we ended our trip here - but previous years we also did the following:
9:00am-11am
Schooner Windsong Sailing - $75 per adult for Day Sail, you can book this awesome sailing cruise here.
*Park in the gravel lot in front of The Shanty, and walk down either dock access ramp to the end of Dock D.
12pm
Lunch:
Cape Charles Brewing Company - 11:30am-8pm, Burgers & gastropub fare
2pm
Cape Charles Museum - 10am-4pm, Museum in a former power plant with local history.
I hope you found this itinerary helpful! There are more blogs on my website about other spots around Virginia, as well as Richmond tips. You can also follow me on YouTube for my travel videos or Instagram for daily updates. Feel free to DM me with any questions! Have a great trip!
💚Lauren Z Ray
