Williamsburg on the Water: A Guide to Experiencing the Area’s Waterways

Photographers and design lovers Jackie Greaney and Paul Havel share their tips for planning a trip that is focused on the Williamsburg area’s waterways and nautical charm, while highlighting some of their favorite photo opps along the way.

1. Hornsby House Inn / Lodging

We adored our stay at the Hornsby House Inn, a historic bed & breakfast located right in the middle of Yorktown. Built in 1933, filled with period antiques, and still family operated, we loved that this B&B was right across from the Victory Monument and just a short walk from the York River. A delicious communal breakfast, included in your stay, is a fun way to meet other visitors!

2. Casa Pearl / Dining

Oysters are such a unique way to get a taste for a coastal region, and Virginia is the largest producer of fresh, farm-raised oysters on the East Coast. We had a fun lunch al fresco at Casa Pearl, a relatively new oyster bar and taco joint that’s focused on fish and shellfish from the Chesapeake Bay region and located in a cute, renovated Texaco gas station.

During our stay, we also ate at Amber Ox, a lively brewpub with a fun Tiki Night/outdoor BBQ setup on Monday nights, and at Fat Canary, a Merchants Square mainstay with elevated dishes like foie gras hazelnut toast and guinea fowl with parmesan gnocchi. We also enjoyed Second Street American Bistro, a casual spot that offers later service and generous portions.

3. Victory Monument / Picnicking

Driving the beautiful Colonial Parkway is a highlight of visiting Williamsburg, and at one end of the drive you’ll find the Yorktown Battlefield and Victory Monument. We thought the grass around the monument overlooking the York River was the perfect place for a picnic. We picked up delicious sandwiches from The Cheese Shop (rye bread, Usinger salami, cheese + their famous “house dressing”) and watched the boats sail by.

4. Schooner Alliance / Sailing

We always try to get out on the water when we visit a coastal town, and we loved setting sail on the York River aboard the Schooner Alliance! The York River is an estuary, which means a saltwater and freshwater mix. We saw many dolphins swimming alongside the boat as we sailed past sites such as the Yorktown Battlefield, the Victory Monument, and the George P. Coleman Memorial Bridge, a unique double swing bridge, all the while learning about the area’s history from the Alliance’s crew.

5. York River State Park and Fossil Beach / Exploring

A trip to Williamsburg includes history, so how about a 2-million-year-old fossil for a souvenir? We woke up early one morning to take a quick 3/4 mile hike in York River State Park, which took us along the river, over boardwalks, and down to Fossil Beach, which is home to the fossils of more than a dozen different shellfish and aquatic creatures— from scallops, clams, and oysters to barnacles, snails, whale bones, and, occasionally, shark teeth. It’s a popular place for beachcombing as weather, erosion, and tides are constantly unearthing new specimens from the cliffs and shore. Visitors may take one fossil home with them as a souvenir.

6. Yorktown Beach / Relaxing

A beach day is possible in Yorktown, too! We loved getting a bit of sun at Yorktown Beach, on the sandy shoreline of the York River, right next to the historic Archer House and Cornwallis’ Cave. We watched the fishermen on the Yorktown Fishing Pier go for flounder and trout, and grabbed an afternoon drink on the patio at The Yorktown Pub.

7. Jamestown Settlement / Learning

No trip to Williamsburg is complete without a visit to Jamestown Settlement, a living history museum that tells the story of the earliest days of Virginia, including the cultural encounters and events that planted the seeds of a new nation. The entire museum is amazing, but we especially loved climbing aboard the Susan Constant, Godspeed, and Discovery, recreations of ships that brought America’s first permanent English colonists here in 1607. Nearby at Historic Jamestowne, visitors can see the original site of the first permanent English settlement in America, as well as an active archaeological dig site.

8. Windmill / The Watermen’s Museum

Virginia’s watermen harvest blue crabs, oysters, clams, fish, and other seafood from the Chesapeake Bay Region, and the Watermen’s Museum in Yorktown celebrates all things related to their craft. This recreation of William Buckner’s Mill, originally built in 1711 and a guidepost on the York River for two centuries, originally drew us in. But we loved touring the museum’s amazing collection of nautical artifacts and model boats, as well as seeing the historic boats being built and refurbished in the boathouse.  

9. Mobjack, Patriot Tours, and Riverwalk Landing / Sipping, Cycling, and Shopping

A number of cute shops in Yorktown caught our eye, and we thought it would be fun to visit them by bike. We rented cruisers from Patriot Tours & Provisions, rode along Riverwalk Landing, and grabbed afternoon coffees at Mobjack Bay Coffee Roasters. We had a fun afternoon shopping for antiques and handcrafts at Black Dog Gallery (fossilized oyster and scallop shell wreaths), the Gallery at York Hall (local river reed baskets), and Yorktown Bookshop (a great collection of nautical antiques alongside vintage books).

10. Waller Mill Park / Paddling

All of our walking, exploring, and biking made for a very active trip, so what’s one more activity? We couldn’t resist taking a paddle on the 360-acre lake at Waller Mill Park. The park has kayaks, canoes, and pedal boats available to rent. We enjoyed paddling our canoe around the pristine lake under a sky of fluffy clouds. More boating opportunities are available at Jamestown Beach, Chickahominy Riverfront Park, and The Marina at Kingsmill.

There are so many opportunities in and around Williamsburg to celebrate, and so many ways to get out on the area's waterways! We hope these ideas inspire you to spend some time by the water the next time you visit Williamsburg. Be sure to snap some beautiful photos along the way! 

About Jackie and Paul:

Jackie Greaney and Paul Havel own a full-service creative studio in Kennebunk, ME. Learn more about them on their website and follow along via Instagram.