3-Day Itinerary in Cape Charles, VA

It’s the start of warmer months here and our 3-day itinerary in Cape Charles, VA is just the ticket to start your summer! An escape to beautiful Cape Charles will help you relax and unwind from the rigors of everyday life.

Check-in starts at 4:00 pm with a warm welcome and getting settled in one of our guest rooms. Cozy and comfortable beds, lush linens and towels, plus all the modern amenities will ensure a wonderful stay. And then there’s The Porch — a perfect place to relax with a cup of coffee or curl up with a good book.

A quiet picnic at sunset is a perfect way to start unwinding and begin embracing the natural beauty here in our little part of the world. A basket filled with a beverage of your choice and a variety of delicious appetizers is carefully prepared for your dining pleasure. Just throw down the blanket we’ve included and all you need to do is sit, relax, and enjoy!

Day 1

A Hearty Breakfast Start

Jim and Tammy’s hearty breakfast will fortify you for a day full of adventure! Plan on savoring authentic Eastern Shore fare with farm-to-table ingredients. Whether it’s from the backyard or delivered from a local farmer, the vegetables and herbs will be the freshest you’ve ever tasted. You may want to relax on the Porch and sip your second cup of coffee as you let your breakfast settle.

Kayaking or Paddle Boarding

It’s time to head out on the water for some great exercise and simple enjoyment of the great outdoors. If you’ve brought your own equipment, venture out from several launches such as Cape Charles Harbor, Oyster, or National Wildlife Refuge. Our Lovin’ on the Water Trail card offers a list for your convenience.

Guided tours are available at SouthEast Expeditions. There are several options available. The Chatham Vineyards tour winds through Church Creek with your guide sharing insights on local wildlife. Once you’ve reached the vineyard, enjoy a complimentary wine tasting and cheese tray. This package also comes with a free bottle of their wine. The Wildlife Refuge tour is top of the list for the nature lover. Gliding through the waters of the Eastern Shore, you’ll discover some incredible regional flora and fauna.

Lunch at Cape Charles Brewing Co.
2198 Stone Rd, Cape Charles, VA 23310
(757) 695-3909

After your adventures on the water, head over to Cape Charles Brewing Co. It’s a family-owned and operated brewery and eatery that has great fresh seafood and juicy burgers. Try a sampler of their beer, you earned it!

Hiking and Biking Trails

Continue in the relaxing embrace of nature out on the southern tip bike and hike trail. This is an easy out and back asphalted trail that winds its way through quiet farmland. With little elevation and low amounts of foot or pedal traffic, this trail is an easy and restful time spent working off your lunch.

Back at the Inn, a guided tour through our own amazing gardens can be scheduled with Tammy, a Master Gardener. She tends these gardens with loving care and will gladly share tips and tricks you can use in your own gardens. The landscape is full of beauty, fragrance, and color in all seasons. It’s a treat for all your senses.

Dinner at Ambrogia Caffe & Enoteca
321 Mason Ave, Cape Charles, VA 23310
(757) 607-3026

Dinner at Ambrogia provides authentic flavors of old-world Italy. Christina, the owner, learned from her mama the traditional recipes that have been passed down from the generations. In addition, Mama taught her the skills of being a warm and welcoming hostess to all her guests. It’s a comfortable sense of home with a little Italian seasoning. Reservations required.

Day 2

Another day dawns with the tempting aromas of coffee brewing and breakfast baking. It’s time to savor the creations of Jim and Tammy. Perhaps you will get to experience our award-winning sweet potato ham biscuits or other delicious offerings each morning.

Visit Museums Rich in History

After sipping your coffee on the Porch, it’s time to head out to experience the amazing arts, culture, and history of Cape Charles. The tour begins at the Cape Charles Museum and Welcome Center. Displays showing items dating back to the 1880s tell the story of Cape Charles’ beginnings. Several buildings are on display, including the Bloxom Station, a GP7 diesel locomotive, the original Pilot House, and more.

From there, the museum tour moves on to a must-see spot: the Barrier Islands Center. The center has a rich history of the men and women who lived on the islands and is now a global historical treasure. The Historical Society of the Eastern Shore is the home of the Ker Place Herb and Kitchen Garden, one of Tammy’s favorite places. Visitors learn about the culinary and medicinal purposes of the herbs used in days past.

Take in the Artwork of Talented Local Artists

From folk art to stunning representations of the beauty of Chesapeake Bay. The Lemon Tree Gallery & Studio has an array of art in all mediums, including live music. These are just a couple of the galleries on the Eastern Shore. This may take your whole day rather than just a couple of hours with the abundance of local talent. Just a block and a half from us, Local-ISH Art is an amazing new gallery. This is a great spot for unique gifts and items made by local artisans.

Lunch at Kelly’s Gingernut Pub
133 Mason Ave, Cape Charles, VA 23310
(757) 331-3222

For a taste of a classic Irish Pub, Kelly’s Gingernut Pub is the place to be. Just sit back, relax, or maybe engage in a game of darts. Originally a bank built in 1907, you can dine in the vault — just don’t let the heavy steel door shut behind you. With a slogan of “Great Drink, Great Food, Great Times!” it’s sure to be a memorable lunch.

An Afternoon of Horseback Riding

After lunch, head out to the Esperanza Riding Company. Their Paso Fino horses will provide an amazingly smooth ride through the beautiful Eastern Shore terrain. Depending on skill levels, the riding pace may vary. However, the main purpose of these rides is to take in all the beauty around you. Meet “the Kids” before you go.

Final Dinner at Hook@Harvey
1011 Bayshore Rd, Cape Charles, VA 23310
(757) 331-2275

For an extra special treat, savor a delicious dinner at Hook@Harvey. Their fresh tantalizing menu is topped only by a gorgeous view of the sunset. It’s a memory to be treasured. Reservations are required.

Day 3

Enjoy a 3-peat breakfast and coffee on the Porch. No hurry is necessary with check-out by 11:00 am.

Before you head home, spend a little time shopping in Cape Charles. One place you won’t want to miss is Peach Street Books, which was once a 1930s Pure Oil gas station. For some “unique mementos” of Cape Charles, visit Chuckletown. For some beachy housewares, stop at The Boardwalk. For unique locally crafted jewelry, you’ll need to visit Moonrise Jewelry. There are so many more, you’ll just have to plan another trip!

Our 3-day itinerary in Cape Charles, VA, could be stretched out to several trips with so much to explore! We would love to host your stays — just be sure to check availability, and don’t hesitate to ask for help in planning your next visit.

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