Ten Great Kayaking Adventures on Virginia’s Eastern Shore

What’s the ideal way to explore the two pristine coastlines of Virginia’s Eastern Shore?

From a kayak.


You’ll feel exactly like John Smith did in 1609 when he arrived in the New World and discovered a remarkable spit of land with the Chesapeake Bay on one side and the Atlantic on the other. No boardwalks or beach rentals three deep here. With one of the most undeveloped coastlines on the East Coast, the wild barrier islands off the Eastern Shore’s coast are the longest stretch remaining on the Atlantic Ocean.

Bring your own kayak or hire an expert outfitter and guide to provide a route, equipment, training, logistics, along with cultural, historical, conservation and ecological insight. Trips can be tailored according to interests, skill level and physical prowess. Click here for a complete list of outfitters when you’re ready to book your kayak adventure.


Kayak Winery Tour: On the Paddle Your Glass Off tour you will leave from a working waterfront on the Chesapeake Bay and paddle to award-winning Chatham Vineyards. Taste wine from grapes grown and bottled on a farm that is four centuries old and then paddle back with a bottle of wine tucked away.
Book with SouthEast Expeditions

Overnight on An Island or a Historic Estate: Head out on the Chesapeake Bay, the world’s second-largest estuary, to camp out on a remote island.  If you’d like more luxurious digs, kayak right up to Sycamore Bend, a historic waterfront estate for the night, or stay in a B&B in the charming harbor town of Onancock. Add to your adventure with an oyster roast, hang-glide or wine tasting.
Book with Burnham Guides

Photo Courtesy Burnham Guides.
Photo Courtesy Burnham Guides.

Wildlife & Ecology: The Eastern Shore’s undeveloped coastlines on two sides include the wild barrier islands and provide rich, protected habitats to observe birds and wildlife. Kayak through off-the-beaten-track Harborton Bay, Gargatha Landing and Wachapreague to observe one of nature’s most complex and delicate ecosystems, the coastal wetlands. You’ll never look at the world the same once you spot the tiny, well-disguised eggs of the tiger beetle hiding in plain sight on the open sand.
Book with Bay Country Kayaking

Chincoteague Pony Kayak Trip: Sure, you can see the famous Chincoteague ponies when they’re rounded up in the spring or fall, or for the big July swim, but if you know where to look, you can sneak up on them in a kayak. It’s a thrill, especially for fans of Marguerite Henry’s famous Misty of Chincoteague book or movie.
Book with Assateague Explorer or SouthEast Expeditions

Cabin on a Deserted Island

Overnight at a Waterman’s Watch House: Adventure out to the Atlantic coast of Virginia’s Eastern Shore and overnight in a rustic waterman’s cottage on a deserted barrier island. You’ll feel alone on the planet as the sun goes down and you are blanketed with the night sky and the complete silence. Watermen once used these tiny huts to watch over their oyster beds.
Book with SouthEast Expeditions

Kayak Rocket Launch: See NASA’s Wallops Island rocket launches from a kayak. Wallops Island rockets were first launched from Virginia’s Eastern Shore in 1945 and today, they carry payloads to the International Space Station, and smaller rocket launches are routine. Major nighttime launches are spectacular and can be seen as far north as New York. Check here for rocket launch schedules.
Book with SouthEast Expeditions or Assateague Explorer

Barrier Island Beach Trip: Depart from the tiny seaside fishing village of Wachapreague and head out through the salt marshes and wetlands to a barrier island. Bring a picnic and spend the day hunting for shells, playing in the Atlantic Ocean and lounging on a deserted beach.
Book with DayTrippers


Virginia’s Seaside Water Trail: Kayak a 100-mile-long sea trail with 37 mapped routes that starts at the Eastern Shore of Virginia National Wildlife Refuge on the south end of the peninsula. Paddle along the Atlantic Coast all the way to Greenbackville on the Virginia Maryland state line. You can do this as a self-guided tour using a map or hire a guide.
Book with Burnham Guides or Plan a Self-Guided Adventure

Watch Sunset or Sunrise From a Kayak: The compelling sunsets and sunrises of Virginia’s Eastern Shore are magnificent no matter where you are, but they’re especially compelling when you’re sitting quietly in a kayak.
Book with Any Outfitter

Kayak Clamming or Oyster Tour: Pull an oyster or a clam right from the water, shuck it and slurp it down. These delicious shellfish grow both in the wild and with help from local aqua farmers on both the bay and ocean sides of Virginia’s Eastern Shore. The region produces most of the clams raised on the East Coast, and the oysters, decimated in the 1980s, are making a strong comeback.
Book with Any Outfitter

To plan your kayaking trip to Virginia’s Eastern Shore click here.

You may also like: Eight Big Outdoor Adventures on Virginia’s Eastern Shore
Explore Virginia’s Eastern Shore by Bicycle
Eight Wilderness Hikes on VA’s Eastern Shore

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