One glimpse of Jamestown from a boat will take you back 400 years. Here, you’re taking in a sight very close to what English settlers must have seen in 1607 as they approached land after a four-month voyage across the Atlantic. The lush Chesapeake Bay region, already home to large numbers of Native Americans, must have looked like heaven to their weary eyes. Though they knew the road ahead would be difficult, the appeal of the landscape must have been undeniable–as it is today.

The frame of a colonial-era structure at Historic Jamestowne (Photograph by Leslie Trew Magraw)

The frame of a colonial-era structure at Historic Jamestowne (Photograph by Leslie Trew Magraw)

The greater Williamsburg area–of which Jamestown is a part–is a fantastic place to be outdoors. During my stay I rented a bike, took long walks, sipped wine in a spectacular setting, and boarded a boat for a cruise down the James River.

Exploring the land from different perspectives gave me a greater appreciation for the complexities of America in its earliest stages–and the spirited community that occupies the site of its earliest permanent English settlement today.

Here’s how to relax, disconnect, and get to know Williamsburg’s wild side:

A 90-minute boat ride with Jamestown Discovery Tours will transform the way you see the “Virginia experiment.” With departures from Eco Discovery Park, it’s easy to pick up the tour after visiting the site of the original settlement or nearby living history museum. Captain Corey Fenton had his cozy boat outfitted to optimize the experience of his passengers; every seat has a great view. You’ll also get close to the surprisingly small ships patterned after the Godspeed, Discovery, and Susan Constant moored at the Jamestown Settlement. “I would have gone mad!” squawked one of the taller men on our tour, after hearing about the severely cramped quarters. Me, too.

Visitors aboard a replica of the "Susan Constant"at the Jamestown Settlement (Photograph courtesy Williamsburg Area Destination Marketing Committee)

Visitors aboard a replica of the “Susan Constant”at the Jamestown Settlement (Photograph courtesy Williamsburg Area Destination Marketing Committee)

The region’s thick pine and oak forests, wetlands, and riverfront find contrast at Yorktown Battlefield. Skip ahead a few generations in history by visiting the site of the last major battle of the American Revolution. The best way to pay your respects to the soldiers who died for independence while absorbing the battlefield’s peaceful beauty is from a bike. There are no rentals at the National Park Service visitor center; instead, pick up a bicycle from Patriot Tours in Yorktown and ride to the battlefield. When you arrive, decide between the seven-mile Battlefield Tour Road or nine-mile Encampment Tour Road, which are also self-guided auto routes.

More serious cyclists should head for the Virginia Capital Trail, two segments of which pick up nearby. From Jamestown, the Greensprings portion is nearly three miles long, while farther out, there is a five-mile section open along the Chickahominy River. By 2015, there will be 50 miles of contiguous trail connecting Jamestown and Richmond, a route I’m eager to try one day.

In addition to churning out excellent wines (read about my foodie favorites), Williamsburg Winery, just ten minutes south of Williamsburg’s city center, presents an appealing entree into a different kind of fertile landscape–glass of wine in hand, of course, and preferably with a plate of charcuterie close by. While the gently rolling hills are quintessential Virginia, you can travel the world by staying on-site at Wedmore Place, a country hotel with 28 uniquely designed rooms and suites inspired by different European regions (think Provence, the Cotswolds, and Bavaria).

Biking: the best way to tour Yorktown Battlefield. (Photograph by Annie Fitzsimmons)

Biking: the best way to tour Yorktown Battlefield. (Photograph by Annie Fitzsimmons)

A few locals told me to go to New Quarter Park, especially if I was “into disc golf.” I can’t say that I am (apparently the park has one of the best courses in the state), but I loved this thoroughly off-the-tourist-track park regardless. There are great biking and walking trails, plenty of places to picnic, and lovely views to be had here.

When the sun begins to set, head for York River State Park, to kayak or canoe the pristine waterways where osprey, bald eagles, and great blue herons abound. When I came for an early evening paddle, a family from Richmond, Virginia’s modern-day capital, told me me that it is “worlds apart” from where they live, but close enough that they come once a month so their kids can get outside. Shutterbugs will appreciate the park’s monthly photography walks (free with admission), where rangers and in-the-know photographers reveal secret vistas and wildlife havens.

Annie Fitzsimmons is on the beat in America. Follow her adventures on the Urban Insider blog, on Twitter @anniefitz, and on Instagram @anniefitzsimmons.

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