Book Tour

A Bike Tour of Williamsburg, Jamestown & Yorktown Virginia

A Bicycle Tour of the Founding of America

Virginia's Lower Peninsula is rich in history:  Home to the first successful English colony in America, the final dramatic battle of the American Revolution,  and the incomparable living historic park that is Colonial Williamsburg.  Bike routes on gently rolling hills and flat terrain connect these sites and more.  Lodge nightly in magnificent inns rich with colonial style and dine in fine restaurants nightly. 

Book this Tour

Colonial Virginia

Virginia's Historic Triangle

Tour Difficulty

Mostly Flat, with a few Rolling Hills


6 Days, 5 Nights


Virginia Crossings, Glen Allen, VA

Nearest Airport

RIC Richmond International


From $2445 per person


9/26/21 - 10/1/21 10/3/21 - 10/8/21

Tour Status

Sept. 26 is full at this time. Please email if you would like to join the wait list. Oct. 3 has limited availability. Call for more information.
Book Tour Download Itinerary
I loved that last meal! I liked the pools too. Williamsburg is an amazing place, and I'm glad we did some of the recommended readings before the trip. The bike path between Richmond and Jamestown is the best I've ever biked.
Karen, Green Bay, WI

ItineraryDownload Itinerary

Day 1

20–42 miles, a few hills

We meet in the late morning at the lovely Virginia Crossings Hotel and Conference Center.  We'll have time for bike fittings for renters and a quick lunch orientation.  Afterwards, our first bike ride will take us from the inn to nearby country roads and a Revolutionary era historic site.  You can opt to spend more time there and shuttle back, or continue biking all the way back to Virginia Crossings.  We'll enjoy dinner onsite as a group.

Day 2

20–60 miles, mostly flat

After a brief van shuttle we'll commence bicycling our way down the Lower Peninsula.  Making use of a combination of back roads and the new Virginia Capital Trail, we'll pass historic James River Plantations.  Arriving at Jamestown Settlement in time for a picnic lunch, the afternoon is yours to explore the facility's outstanding exhibits and interpreters who tell the story of Jamestown and the founding of Virginia.  After an optional post-history immersion pedal through beautiful Island Drive, we'll make our way a short distance over to our luxurious abode for the next two nights: Wedmore Place at the Williamsburg Winery.  We will enjoy a private catered dinner onsite. 

Day 3

30–60 miles, mostly flat with a few hills

After enjoying Wedmore's elegant breakfast, we'll depart on bikes for the Jamestown-Scotland Ferry.  This short ferry takes us across the James River to rural Surrey County.  Miles of rural cycling await as well as interesting Chippokes Plantation State Park.  The original land grant for the property dates from 1619.  Park exhibits trace the evolution of farming and forestry in the area.  After a picnic lunch, we'll make our way back to the ferry across the James.  From the ferry dock in Jamestown, it is a short ride to Williamsburg and our home for the next three nights, Williamsburg Lodge.

Day 4

12–50 miles, a few hills

The historic district of Williamsburg, the second Colonial Capital of Virginia (the first was Jamestown) has been painstakingly restored and replicated over many years by The Colonial Williamsburg Foundation.  Leadership (and money) for this project came from John D. Rockefeller, Jr. and other local and and national leaders in the early 20th Century.  Today, we can tour homes, gardens, government buildings and churches in the walkable historic area, and interact with interpreters in period costume.  Passes to Historic Williamsburg will be provided so that you may enjoy the afternoon touring on your own schedule.  We'll move into the Williamsburg Lodge, a beautifully equipped property that is part of Historic Williamsburg. Dinner is "on your own" this evening, with numerous restaurants available within a short walk.   

Day 5

16–45 miles, a few hills

We'll start the day with an early cycling diversion through Historic Williamsburg before the crowds arrive, then pedal Colonial Parkway to Yorktown.   In October of 1781, American and French forces led by General Washington pinned General Cornwallis' British army against the York River and began a siege.  Cornwallis surrendered on October 20, effectively ending the war.  Tour the NPS visitor center, then pedal the paved battlefield and encampment loops to join our private tour guide at key sites.  He will provide fascinating insights into the personalities who made history here.  Return to Historic Williamsburg for a second night.  Our group dinner tonight will be at the A Chef's Kitchen.  Watch Chef John Gonzales prepare a fresh gourmet meal for you in his demonstration kitchen.

Day 6

20–50 miles, mostly flat with a few hills

Time to leave the "Historic Triangle" behind.  After a brief shuttle, we pedal north and west and make our way back to Virginia Crossings.  Along the way, enjoy varied scenery that includes wooded areas and lakes.  There will be an opportunity to shower, and we'll enjoy a buffet lunch at the hotel.


$2,445 - $2,545
Bike Rental
Single Room Supplement

Low end of tour price range reflects the 6 month Early Bird Discount.  High end of price range reflects no Early Bird Discount. 

What's Included in Your Tour Price


5 nights at boutique inns and hotels


Dinner on Nights 1, 2, 3 & 5; All lunches except 1; All breakfasts; snacks; and hors d'oeuvres most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

Complimentary Airport Transportation from Richmond

Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Richmond Airport area (RIC).  Timing formally coordinated 2 weeks prior to tour date.

More details on what's included: 

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Night 1

Virginia Crossings Hotel and Conference Center

(also available for additional nights prior)

Our AAA Four Diamond hotel offers unique dining options along with comfortable and efficient accommodations. Recreational choices include outdoor pool and whirlpool, volleyball, basketball, horseshoes, world-class golf and an extra large fitness center. Recent renovations bring color and life to all public areas and meeting rooms.  Virginia Crossings is now operating as a Tapestry Collection by Hilton.

Carolina Tailwinds Trailer at Wedmore Place

Night 2

Wedmore Place at the Williamsburg Winery

A European-style country hotel nestled into 300 acres of green space, Wedmore Place features 28 uniquely designed rooms and suites. Each room is named and patterned after a different province of Europe and is decorated with antiques and paintings to reflect the culture and history of that province. All rooms feature wood-burning fireplaces, 10’ ceilings and king size beds. Guests can also enjoy a meal at one of the property’s two restaurants, or a tour and tasting at the adjacent Williamsburg Winery.

Nights 3, 4 & 5

Williamsburg Lodge 

Enjoy your stay in a room decorated in fashions drawn from Colonial Virginia–style fabrics, which are vibrant as they are classic—and all of them are nonsmoking. Aside from its cozy atmosphere, the Lodge puts comfort and relaxation in the forefront.  Just steps away from the Lodge are all of the historic buildings of Colonial Williamsburg as well as the restaurants and boutiques of Merchants Square.



The terrain is a mix of flat terrain, paved bike paths and gently rolling hills, making it accessible to all ability levels.  Road bikes and hybrid style bikes are both appropriate.  

This 6 day tour offers routes of 25 - 50+ miles each day (at your option).  Less ambitious cyclists can take advantage of short cuts and "leap frog" van shuttles along the route to tailor the route to their needs.  

Tour Point of Origin:

Virginia Crossings Hotel & Conference Center, 1000 Virginia Center Pkwy, Glen Allen, VA  (804) 727-1400

Getting to the Tour Start (Virginia Crossings, Glen Allen, VA)

Driving: Approximate travel distance to Virginia Crossings--

  • Atlanta, GA:  542 miles
  • Louisville, KY: 568 miles
  • Charlotte, NC: 303 miles
  • Pittsburgh, PA: 340 miles
  • Washington DC:  100 miles

Airports: Richmond International (RIC) is approximately 15 minutes from Virginia Crossings.  It is served by most major airlines.

Ground Transit: Taxi, limo, and shared sedan service is available to and from the Richmond airport.

Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Richmond Airport area (RIC).  Pickup timing formally coordinated 2 weeks prior to tour date.

Parking: We have arranged for long term parking there for the duration of your tour.  We will end the tour at the same inn with an opportunity to shower there prior to departure.

Arrival/Departure Timing

Arrival time on the first day of the tour is 11:00 a.m. if renting equipment from us, or 12:00 p.m. if bringing your own bike.  Guests will want to meet us at these times dressed in bike clothes, or ready to change into them.

We plan to wrap up around 3:00 p.m.  Your return flight should be no earlier than 5:00 p.m. that evening.

Extend Your Vacation

Before or after our activity packed tour, you may want to tack on a few days.  There is a lot to do in and around nearby in Richmond if you have time. 

American Civil War Museum:  Learn about the history of the country’s toughest times exploring the world’s largest confederate collection.

Maymont:  A breathtaking 100 acre estate home to James and Sallie Dooley in from 1892 to 1925.

Monument Avenue: It is well worth the brief 5 mile ride to take in the architecture and the magnificent monuments on this tree-lined street.

Virginia Museum of Fine Arts: Admission is free into one of the largest art museums in North America.

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