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Colonial Virginia: Riding the Road to Independence

National ParksCycle back into American history along the Colonial Parkway on an exciting journey that traces our country’s founding—from the Jamestown settlement, to the time of revolution in Williamsburg, and on to independence in Yorktown. Off our bikes we’ll stay at the AAA Four-Diamond Kingsmill Resort and enjoy a tasting at the Williamsburg Winery.

  • Activity Level: Easy
  • Daily Mileage: 15 - 35 mi
  • Daily Biking: 2 - 4 hr
  • Small Groups: 20
  • Biking Activity
  • Perfect for those trying a bike vacation for the first time.

Why You'll Love This Tour


Colonial Virginia: Riding the Road to Independence Bike Vacation

The beauty of southeastern Virginia by the meandering James River, cycling routes as gracious and accommodating as Southern hospitality, and the drama of our Colonial heritage are all yours on this relaxed journey through natural splendor and American history. With five nights in sumptuous 4-star resorts and inns, you’ll be pampered and refreshed, ready for exploring the Jamestowne settlement, the battlefield of Yorktown, the Colonial richness of Williamsburg, and many other revealing sites. You’ll also enjoy two delightful picnic lunches, a winery tour and tasting, a tour of the stately Jones-Stewart Mansion, and free access to dozens of fascinating exhibits and museums.

Cultural Highlights

  • Savor 5 nights in wonderful 4-star resorts and lodges
  • Cycle to Historic Jamestowne, America’s first settlement
  • Discover the settlement, museum, and living-history exhibits
  • Gather for a fresh picnic lunch prepared by your Trip Leaders
  • Ride the scenic Jamestown Island Driver on the way to your resort
  • Tour the Williamsburg Winery, with a tasting and included lunch
  • Encounter Colonial Williamsburg on a guided walking tour
  • Enjoy the use of an included pass to dozens of exhibits and museums
  • Pedal the siege-line loops where the Battle of Yorktown was fought
  • After an included dinner, consider a tavern stop for a Colonial quaff
  • Ferry the James River to explore Chippokes Plantation State Park
  • Tour the Jones-Stewart Mansion and enjoy a picnic lunch

What to Expect

This tour offers primarily easy terrain with some rolling knolls but no extended climbs. The Colonial Parkway is free of commercial vehicles and posts a 45 MPH speed limit. Hybrid bikes are recommended for their smoother ride on the Parkway’s concrete aggregate surface. It’s possible to complete the week without need to shuttle. Of course, our VBT van support shuttle is always available for those who need assistance or wish for a shorter ride option.

Average Daily Mileage: 15 – 35 miles
Average Cycling Time: 2 – 4 hours

Climate Information

Average High/Low Temperature (°F) – Williamsburg
Apr  66º/48º  May  77º/59º  Sep 78º/62º  Oct 70º/51º

Average Precipitation (in.) – Williamsburg
Apr 3  May 3.5  Sep  4  Oct 3

What’s Included:

  • 5 nights in four-star resorts and lodges
  • 11 meals—5 breakfasts, 3 lunches, 3 dinners
  • FREE use of our custom VBT bicycle and helmet
  • Service of two VBT Trip Leaders
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Daily admission to Colonial Williamsburg’s 23 historic sites, demonstrations of 18th-century trades, and two art museums
  • Guided visits in Jamestown, Colonial Williamsburg and Yorktown
  • Transfers
  • 5% Frequent Traveler Credit to use on your next VBT vacation – at least $99 per person
  • Good Buy Plan

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Land Only Single Supplement: $545

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
Or, Expand All Days
DAY 1: Arrive in Williamsburg

The tour begins at the Kingsmill Resort in Williamsburg, Virginia. If you are flying to Richmond, Virginia, James River Transportation will make one complimentary transfer for VBT guests from the Richmond International Airport (RIC) to the resort. The shuttle works on a “show and go” basis and will make its only departure from the airport to the resort at 1:30 p.m. Shuttle reservations are not required or available. You can find information on the shuttle at the “James River Transportation” counter at the bottom of the escalators, in the ground floor baggage claim area. Counter staff will direct you to the location for meeting the shuttle.

Please note that the shuttle departs promptly at 1:30 p.m. If your flight arrives after this time, you will need to arrange your own transportation to the Kingsmill Resort at your own expense. The following companies offer transportation: James River Transportation (804) 249-1052, Airport Taxi (804) 233-4444, and Galaxy Cab Company (804) 560-4408. Travel time from Richmond International Airport is approximately 60 minutes. Taxi fare is approximately $120.

For guests driving to the tour, parking is available without charge at the Kingsmill Resort during your stay in Williamsburg. Please note that your car will need to be moved to one of the resort’s remote lots for the remainder of the tour when you check out.

Meet your VBT Trip Leaders at 3:30 p.m., dressed in your cycling clothes, for a bike fitting and brief cycling-skills clinic, followed by a warm-up ride. Afterwards, you are welcome to enjoy some free time to discover the resort and settle into your room before gathering at 6:00 p.m. for an orientation meeting and welcome cocktail. Then enjoy dinner while admiring the view of the James River.

Hotel: Kingsmill Resort
Meals: D
Daily Options: 5 miles

DAY 2: The Colonial Parkway / Historic Jamestowne / Jamestowne Settlement / Jamestown Island Drive

Today’s ride takes you to the site of the first English settlement in the United States, Historic Jamestowne. Now part of the Colonial National Historical Park (along with the Colonial Parkway and Yorktown Battlefield), this is the site where, in 1607, more than one hundred intrepid colonists set up the first permanent English settlement in America. These early settlers endured enormous hardships, but Jamestown survived and became Virginia’s first capital. You’ll have a guided visit that brings it all to life. Then tour the Jamestown Settlement, a museum operated by the State of Virginia, and enjoy its living-history exhibits.

Your leaders provide delicious fuel for more cycling with a picnic lunch. You’ll have time to ride the scenic Jamestown Island Drive before returning to your resort.

Enjoy dinner on your own this evening in one of the resort’s five restaurants. There are some great options to choose from, along with the beautiful riverside setting.

Hotel: Kingsmill Resort
Meals: B, L
Daily Options: 15, 21 or 37 miles

DAY 3: Williamsburg Winery / Colonial Williamsburg / Chamber Music by Candlelight

Sleep in or enjoy the early morning for activities at the resort. Ride out from the resort mid-morning and make your way to the Williamsburg Winery. Situated among the rolling vineyards, the winery has produced many award-winning vintages, and you’ll sample some during a guided wine tasting. Next door, enjoy an included lunch at the Gabriel Archer Tavern.

Back on your bike, ride the short distance into the very center of Williamsburg en route to your accommodations for the next three nights, the Williamsburg Lodge. You’re in a prime location, adjacent to the Colonial Williamsburg Historic Area. This afternoon you are treated to a private, guided walk through some of the Revolutionary City’s highlights. You’ll see the magnificent Governor’s Palace, the house “fit for a King’s representative,” before touring the Capitol, where in 1776 Virginia’s patriots voted for independence and a new state constitution. You’ll receive a pass that allows unlimited entry into the Historic Area during your stay. Explore up to 35 exhibition sites, choose from more than 20 shops and self-guided tours each day, and have access to two world-class art museums.

Your Trip Leaders can recommend great options within an easy walk for dinner on your own tonight. If the spirit moves you, come along after dinner for some candlelight chamber music at historic Bruton Parish Church.

Hotel: Williamsburg Lodge
Meals: B, L
Daily Options: 13, 17 miles

DAY 4: Yorktown Battlefield / Yorktown Victory Center / Dinner in Williamsburg

This morning, you’re back on the Colonial Parkway, this time heading east to Yorktown where, on October 19, 1781, a surrounded British army surrendered to George Washington. A siege by the Continental army and French allies had rendered General Cornwallis’s army defenseless. Once the British army surrendered, the American Revolution was over, and our nation achieved its independence.

Watch the film “Siege at Yorktown,” and then ride the seven-mile Battlefield Tour loop along American and French siege lines or the nine-mile Allied Encampment Tour loop.

Lunch is on your own in one of Yorktown’s restaurants. Then visit the newly expanded Yorktown Victory Center to discover the lives of those who witnessed the American Revolution. You’ll return to Williamsburg via the scenic parkway.

Dinner is included tonight in a fun, local restaurant. On the walk back to your lodge after dinner, you may be tempted to stop in at one of the traditional 18th-century taverns and try a taste of colonial tipple!

Hotel: Williamsburg Lodge
Meals: B, D
Daily Options: 13, 18, or 32 miles

DAY 5: Chippokes Plantation State Park

After breakfast, you’ll ride to the Scotland/Jamestown Ferry terminus at Jamestown. The ferry will take you on a 15-minute ride across the wide James River to rural Surry County where the land is truly rural. Fields of peanuts, soybeans, cotton, and corn are the order of the day, and together with the river they make for some serene and scenic…….. riding.

Your destination is the Chippokes Plantation State Park. One of the oldest working farms in the United States, since 1619, this riverside park is a living historical exhibit as well as a beautiful place to explore by bike. You’ll have a private guided tour of the Jones-Stewart Mansion and enjoy a picnic lunch prepared by your Trip Leaders. You’ll return to Williamsburg mid-afternoon by ferry and parkway.

There is time to take a swim or grab a refreshing drink. Then gather with the group for a farewell dinner celebration tonight.

Hotel: Williamsburg Lodge
Meals: B, L, D
Daily Options: 15, 18 or 34 miles

DAY 6: Colonial Williamsburg / Depart for home

Take advantage of your final morning to go back into Colonial Williamsburg, play a round of golf, enjoy the Spa at Colonial Williamsburg, or relax with a good book over a second cup of coffee. Perhaps you’ll choose to visit Wren Hall on the adjacent campus of the College of William and Mary. The iconic red brick building still contains some walls from its original 1700 structure. The College of William and Mary is the country’s second oldest institution of higher education.

Lodge checkout time is 11:00 am and you may store your bags with the lodge. VBT has made arrangements for a shuttle from the lodge back to the Richmond International Airport (RIC). It departs Williamsburg at 12:30 pm and travel time is approximately 60 minutes. If you drove to the start of the tour, your leaders will shuttle you back to the Kingsmill Resort to retrieve your car at 12:30. We recommend a flight out of Richmond no earlier than 3:30 pm.

Meals: B
Daily Options: Non-riding day

Virginia Bike Tour Map

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Kingsmill Resort

The Kingsmill Resort is located along the scenic James River.  Guestrooms feature a private balcony or patio, Keurig coffee maker, plush robes, complimentary Wi-Fi, and an average 375 square feet of luxurious living.  Rooms are spread across the resort in “villas,” adding to the quiet, outdoor feel of the property.  This AAA Four-Diamond rated resort features five restaurants, 15 tennis courts, two golf courses, a newly renovated spa and sports club, and three swimming pools.
Free WiFi Included

Williamsburg Lodge

Enjoy a relaxing hotel escape in the heart of the Revolutionary City. Just steps from the action, the inviting lodge boasts a world-class restaurant and convenient access to spa and golf recreation amenities. Guest rooms feature modern amenities, including free Wi-Fi, an iron and ironing board, Keurig® brewer, flat-screen television, and digital clock radio. Fresh sheets and towels along with maid service are provided daily.  A state-of-the-art fitness facility with daily group exercise classes is located next door at The Spa of Colonial Williamsburg and is available without charge to all lodge guests. Guests have access to two outdoor pools (one of which is heated), as well as an indoor pool located at The Spa of Colonial Williamsburg. You’ll appreciate the attentive staff and top-notch facilities of this property, a member of the Historic Hotels of America.
Free WiFi Included

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