Day Trips for the Adventurous

Looking for more of an adventure? Here are some exciting day trips for the true adventurous explorer of the Eastern Shore.

Tangier Island

Tangier Island is fishing village much like it was 100 years ago, even retaining it’s “Old English” accent among some locals. Located in the Chesapeake Bay, this island village is accessible by ferry which runs seasonally from late May through early October. The only ferry departing from the Eastern Shore in Virginia is from Onancock and is a one-hour trip, each way. Spend the day on a rented golf cart or bike exploring and eat at one of the few restaurants that dot the island.

Gordon Campbell, At Altitude Gallery

Chincoteague, Wallops, and Assateague Islands

Your adventure to Chincoteague and Assateague Islands begins in Wallops Island. The NASA Wallops Visitor Center is a great place to visit for all ages. You can see exhibits, videos, and models of past and present space research on the Eastern Shore. If you time your trip just right you can watch a rocket launch.

Chincoteague is known for the ponies that were made famous by the book and movie, Misty of Chincoteague. The island has tourist type offerings like mini-golf and a small water park outside the KOA campground (open to the public). There are lots of places to eat during your visit (Don’t miss Pico, the best taco place around!) and several famous ice cream stops. My favorite is Island Creamery and others love Mr. Whippy which has been around for 50 years. Don’t miss the Chincoteague Museum which is full of the Island’s treasures, including the actual Misty of Chincoteague (tastefully stuffed and on display)!

Assateague Island is accessed by a small causeway connecting to Chincoteague. This is a national park is well worth the visit. There you might get a glimpse of the ponies in the marsh on your drive around the park. You can walk or bike several trails, hike to the lighthouse, or make your way to the Atlantic Ocean (this is the only true “beach” ocean access on the Eastern Shore of Virginia). The pony swim takes place every July when the Salt Water Cowboys herd the ponies across the channel from Assateague to Chincoteague for their annual check-up and the fireman fundraiser auction. Don’t worry, these ponies can swim! This one week event is great for horse enthusiasts of all ages. If you can’t be there for the pony swim, try a kayak or boat tour with Assateague Explorer Cruises and Kayaking or a boat excursion with Cowboy Cruise Company or Daisey’s Island Boat Tours where you can watch the ponies.

Saxis Island

Like Tangier, Saxis Island, is remote and sleepy fishing village well off the beaten path. There is a causeway that takes you to the island from the mainland. Pristine water and marsh views are on all sides as you make your way to the island. There is a public beach access off of Matthew’s Road where you can search for sea glass in all the colors of the rainbow (I even found the elusive peach color!). The shoreline disappears during high tide so make sure you check the tides before you go.

Hang Gliding

Located at Accomack County Airport, Virginia Hang Gliding offers tandem flights with views of the Eastern Shore. Per their website, “We are passionate people who want to share an amazing experience with you, your family and your friends. We offer experiences ranging from heights of 2,000 ft to 5,300 ft (approx. one mile), each one with a spectacular view of the Eastern Shore, Chesapeake Bay, Atlantic Ocean, and the Barrier Islands. Our team has several decades of experience and its our priority to give you a safe and enjoyable flight.” Reserve your flight today!

Boat and Fishing Tours

Whether you are looking for a sunset cruise, a fishing trip to the Chesapeake Bay, a boat tour of the Barrier Islands, or a sail boat cruise there are many options to choose from.

  1. Miss Jennifer leaves from Sun Outdoors (formally Cherrystone Campground) for sunset cruises and other boating adventures.

  2. Captain Rick (757) 442-4363

  3. Tidewater Charters - Chesapeake Bay Fishing Charters.

  4. Seay Stories Sportfishing sport fishing and sunset cruises.

  5. Schooner Windsong is a 47' Tancook Schooner homeported in Cape Charles, Virginia (2023) where she offers 6 person private charters on the Chesapeake Bay and surrounding waters.

  6. Seaside Ecotours with Captain Meriwether Payne - Barrier island birding & photography trips. Nature & sunset cruises; island boat trips for picnics. Leaves out of Wachapreague.

  7. Sho-Nuf Sport Fishing/Charters - Come fish on the updated 35’ Bertram with a huge cockpit and salon.

  8. Top Dog Charters - Fishing charter

  9. Captain Dave Fauber - Book a charter on the only authentic, wooden hull deadrise boat charter operating out of the Cape Charles area! capt.dave@localhoneyesva.com or text 757-695-1025.

Water Sports

There are lots of ways to enjoy the water during your visit! Located at the Harbor, Poseidon Water Sports, owned by Raven and his wife Elena, is the place to rent jet skis. Call to reserve your jet skis for your group. You can book a kayak, paddle boards, a boat, or bikes for your vacation with them too. Located in Cheriton, South East Expeditions will deliver bikes and kayaks to your home during your stay. They also offer guided kayak tours-check their website for tour schedules and booking. Consider learning to sail with Cape Charles Sailing Camp adult classes located in the Marina. Private lessons and group excursions also available.

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