Explore the rich tapestry of Virginia’s history as you journey on a colonial Virginia adventure. Virginia’s Lower Peninsula serves as the backdrop for this immersive experience, where you’ll trace the footsteps of early settlers and explore the roots of American democracy. Tour Colonial Williamsburg’s historic streets, soak up the sleepy charm of Smithfield and enjoy a history rich Richmond walking tour, on this diverse cycling adventure.
…‘Company’ is misleading: this is a personal experience…Count on excellent routing, craft-quality laminated and color-coded cue sheets, a daily pre-ride briefing, convenient and dependable sag support, and smaller, friendly groups. The clinchers for me, though, were the gourmet meals and the accommodations at small inns…I’ve been on 3 different trips with them now, and all cycling agendas have been represented and handled on each trip.
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Trip Overview
Price
Early bird discount: $2825 per person
Full price: $2925 per person
Bicycle rental : $100
Single room supplement: $625
Upcoming tour dates & status
- 4/27/25 – 5/2/25
- 5/4/25 – 5/9/25
- 9/28/25 – 10/3/25
- 10/5/25 – 10/10/25
Meeting/Departure Point
Nearest Airport
RIC Richmond International
Duration
6 days, 5 nights
Tour difficulty
Mostly flat, with a few gentle hills
Included
- Lodging:
5 nights at boutique inns and lakefront resorts. - Meals:
3 dinners, 5 lunches, 6 breakfasts, snacks, and hors d’oeuvres on most nights. - Full Route Support & Luggage Transfer:
Service of 1 – 2 support vans on route every day. - Complimentary Airport Transfer from Richmond:
Carolina Tailwinds picks up on the morning of Day 1 and drops off in the early afternoon on Day 6 at the Richmond Airport area (RIC). Parking will be arranged at an off-airport lot. Timing formally coordinated 2 weeks prior to the tour date.
Group Size
Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours
About your guide
Expert guides ready to show you the hidden wonders of each and every destination
What You’ll See & Do
Day 1
20–42 miles, mostly flat terrain
After a group shuttle from airport parking at Richmond International Airport, we will all arrive together at Smithfield Station in downtown Smithfield, VA. 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 quiet country roads dotted with farms, forest, and creek and marsh crossings. A couple of distance options are available, as well as strategic van shuttles for any who want more time back in town. We’ll enjoy dinner as a group at a local favorite.
Day 2
20–60 miles, mostly flat
This will be a lovely full day of cycling the country roads in Isle of Wight and Surry Counties. We will have options for everyone. One highlight will be a stop at Hampton Roads Winery for wine tasting and a picnic on their lovely grounds, complete with their entertaining “goat tower.” Those who want to get back to Smithfield to do some shopping will have that option. Downtown Smithfield is a quaint business district dating to 1752, although the first English from across the river in Jamestowne settled the area in 1634. Multiple museums and art galleries offer a look back at the long history of the area, and you will have an opportunity to find local artwork. And, you’ll want a “selfie tour” with the many local-artist-painted hog statues that are scattered about town. Smithfield is proud to be the “ham capital of the world.”
Day 3
30–60 miles, mostly flat with a few small hills
After breakfast, it is time to leave charming Smithfield behind. We pedal more quiet country roads to the Jamestown-Scotland Ferry, which will take us across the James River. On the way, we will pass the oldest brick dwelling in North America, Bacon’s Castle, which is now a state historic site. Just on the other side of the river, we reach Historic Jamestowne, site of the first successful English Settlement in North America. Now a very active archaeological site, we will enjoy a talk by one of the expert interpreters employed by Preservation Virginia. Enjoy lunch, exhibits and monuments onsite afterwards. A short shuttle or optional more urban bike ride will take us to Williamsburg Lodge at Historic Williamsburg. We will enjoy dinner as a group in Williamsburg.
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 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
25–61 miles, a few hills
Today is a cyclist’s delight! The Virginia Capitals Trail is a 51 mile, beautifully paved, dedicated bike path traversing the distance from Jamestown to downtown Richmond. On the way, it passes woods, farms, historic sites, parks and a quaint county courthouse. As it approaches downtown, the trail slips through a newly revitalized area where we will enjoy lunch and savor the ride. It is just a mile or two further to our hotel for the final night, located in Richmond’s historic Shockoe Slip neighborhood. Our final dinner together will be at a fantastic Richmond eatery.
Day 6
3–5 miles, walking tour with some hills
On our final day together, we are going to leave the bikes in storage and enjoy a fascinating guided walking tour of downtown Richmond. The city has been at the center of Virginia and national history through momentous events and movements. There is more to see here than we can possibly include, so you will want to consider extending your stay in the area.
What’s Included in Your Tour Price?
Tour prices are per person rates and include all of the following:
- Lodging costs (double occupancy rooms), including all taxes and fees
- All breakfasts and most lunches
- All dinners described in the tour itinerary (alcoholic beverages in restaurants are generally not included)
- Morning and afternoon snacks
- Route planning and detailed laminated cue cards daily
- Guide support along the route
- Van support along the route
- Luggage transfer
- Fees for all ferries, tolls for all highways and any park entrance or guided tour fees where noted
- Transportation back to starting point
- Costs for any special activities such as canoeing, kayaking, sailing or rafting where noted
- Carolina Tailwinds t-shirt or day bag, water bottles, complimentary digital photo files from your tour
- Gratuities for restaurants at included meals and gratuities for housekeepers at included lodging
Please note:
All lodging costs are based on double occupancy. The single room surcharge rates apply to single room occupants.
Single travelers who desire a roommate match will be paired with other tour guests of the same gender in a room with two beds, if available. If a match can’t be found for a single traveler, a single occupancy surcharge will be assessed. To find out if a roommate match is available, call us. We will be happy to put you on a waitlist for a match if one is not already available.
Single travelers may request a private room, subject to availability, and to the single room surcharge rate payable in full at the time of the reservation.
Transportation to the tour starting point, including airfare and any airport transfers, is not included in the tour price. We can assist you with making any airport transportation arrangements or advise you on the nearest and most convenient airport.
Alcoholic beverages at restaurants are not generally included . A separate beverage tab may be run for anyone who would like a drink with dinner. Settling this tab will be the responsibility of the individual participants.
Bicycle rental is available as an option (prices above). We have road touring bikes and hybrid bikes for your use and invite you to forego the hassle of transporting your bike to and from the starting point. Click here for more information on the equipment available for your use.
Want to know more about our policies, terms and conditions? Click here to review our deposit requirements, cancellation policy and more.
We will be happy to address any additional concerns or questions you may have.
Simply email us at our Contact Us page, or call us at 1-888-251-3206 (local number is 336.794.1054). Ready to make your reservation? Click here to reserve a spot online, or call us at 1-888-251-3206 (local number is 336.794.1054).
Travel Insurance: We strongly encourage you to consider travel insurance. You may research and compare competing travel insurance policies at websites such as www.squaremouth.com.
Where You’ll Be Staying
Nights 1 & 2
Smithfield Station
Smithfield Station is a family run hotel, restaurant, marina and shopping complex on the banks of the Pagan River and at the edge of downtown Smithfield. And short walk takes you into the heart of downtown, where shops and museums await. Many rooms have balconies overlooking the marina and the surrounding salt marsh.
Nights 3 & 4
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.
Night 5
Courtyard by Marriott, Downtown Richmond
Located in Richmond’s historic Shockoe Slip neighborhood, our hotel is just steps away from the junction of the Virginia Capital Trail and the Canal Walk.
Get Prepared!
Cycling
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
Richmond International Airport area.
Getting to the Tour Start (Chestertown, NY/Saratoga Springs, NY):
Driving: Approximate travel distance to RIC–
- 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 downtown Richmond. 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 is formally coordinated 2 weeks prior to the 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 airport parking area.
Arrival/Departure Timing
Arrival time on the first day of the tour is 9:00 a.m. Everyone will be shuttled from RIC to Smithfield, VA. If renting equipment from us, your fitting will take place upon arrival in Smithfield. Everyone will meet at 12:00 p.m. for lunch and a quick orientation. Guests will want to meet us at these times dressed in bike clothes, or have them ready to change into them.
On the last day, we plan to get you back to the airport area by 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. https://acwm.org/
Maymont: A breathtaking 100 acre estate home to James and Sallie Dooley in from 1892 to 1925. https://maymont.org/
Virginia Museum of Fine Arts: Admission is free into one of the largest art museums in North America. https://www.vmfa.museum/
Rental Bikes for Your Tour
Our Selection
Women’s Road Bike ⇒
⇐ Men’s Road Bike
Hybrid Bike Small ⇒
⇐ Hybrid Bike Large
Step Through Bike ⇒
Why Choose This Tour?
Enjoy picturesque rides along quiet country roads dotted with farms, forests, and creek crossings
Indulge in a delightful wine tasting experience at a local winery
Step back in time at Historic Jamestowne and discover exhibits and monuments commemorating America’s colonial history
Immerse yourself in the living history of Colonial Williamsburg and interact with interpreters in period costume as you stroll through the charming streets of this colonial capital
Embark on a scenic journey along the Virginia Capitals Trail, a beautifully paved bike path winding through woods, farms, and historic sites
See What Our Customers Say About Us
We love this company. We have toured with them three, going on four times and their attention to every detail and their organization skills keep us coming back for more. we have toured with three other companies, vbt, bike vermont, and pedal and sea adventures, and they surpass all of them. Food especially is excellent.
Carolina Tailwinds gives every attention to detail towards their customers. The routes they map out are clear and safe. The accommodations that Carolina Tailwinds select are 5 star all the way, from the lodging to the restaurants. The guides are friendly and accommodating to the cycling level of their guests. The size of the tour group are intentionally small to give the customer that undivided attention they deserve on their vacation.
We had used several bike tour companies and thought that they all did a good job. However, Carolina Tailwinds’ tours are operated by the owners of the company. Thus, their level of service exceeds that of other companies. We have now completed 5 tours with them and have another scheduled. Greg and Anne, the owners, are now like members of our family.
We are in our mid-seventies & have just re-discovered the joys of biking the past 3 years, biking over 2500 miles each of the last 2 seasons mostly hear in upstate NY. We’ve started the past 2 seasons with a Carolina Tailwinds tour & plan to do the same again this season. Anne & Greg just do a terrific job guaranteeing a wonderful vacation for us.
We did the Florida tour with a group of 16. The inns selected by Anne and Greg were a pleasant surprise as were the restaurants. Steve’s patience and guidance while biking was greatly appreciated. We have toured together before but this was the most supported experience we have had. Their bikes were excellent. I highly recommend scheduling with this company.
Tailwinds offers routes that can vary from easy to challenging, but that are always scenic and engaging. The support on the road is absolutely best in class, the lodgings are always interesting, and the food is terrific. Best of all, the owners and guides personify “customer service.” Taking a Tailwinds tour is always the highlight of my cycling year. All of this at prices which are reasonable.
We just got back from a fantastic vacation with Carolina Tailwinds. They were super accommodating and fun. The trip had good variety including cycling, two boat rides, beach walk, kayaking, amazing food and happy hour every day. Every expectation was exceeded as they booked a private tour for my husband’s birthday bash. Equipment was fantastic and the guides were personal me and knowledgeable. Booking was easy and every detail was take. Care of. Thank you to the whole team.
We are two retired friends who left our non-cycling husbands at home to have a biking adventure. We throughly enjoyed our Florida tour…Anne and Greg attending to every detail…Although it seemed we were on our own, our guides were at our backs to provide snacks, sun screen, and any assistance needed…The bikers we rented from CT were fitted to us and were maintained in perfect condition…FIRST RATE! We’re ready to book another CT trip!
We have completed 4 trips with Anne and Greg and have another on reservation. Their attention to detail is evident throughout the tour but especially in the excellent route selection. Good riding is of course why most people go on a bike tour and we have never been disappointed with the miles they carefully select. Good food, nice accommodations, interesting off bike activities and leisurely happy hours all adds up to a relaxing vacation.
This company is awesome! I’ve been on several week long tours and this is by far the best company. My husband and I just completed our second tour with CT and every aspect was first class. The guides are attentive no matter what your skill level. We’re planning a third trip next year.!
…Having been on several other bike companies’ tours I have a good perspective to highly recommend Carolina Tailwinds…They were perfectly organized, personally knowledgeable of the routes, and prepared for everything we wanted or needed for a great week…All through the week CT added fine touches to our trip which you’ll just have to experience on your own CT tour. You’ll have an awesome week.
Excellent value. Routes, accommodations, food, activities, support, and equipment were all top notch. Superb attention to details big and small. I have toured with nearly a dozen companies. They were all good, but Carolina Tailwinds has been my favorite. You can spend more, but you won’t get more than you get from Anne and Greg.
The attention to detail and the readiness to accomodate requests from the riders separate Carolina Tailwinds from any other tour group that I have ridden with. One other feature that has to be mentioned is the standard of the accomodations and the food. They are both of the highest standard. The Carolina Tailwind tours are fun!
…The scenery was abolutely spectacular! Traffic was light and road conditions excellent. The routes were well-planned with detailed cue sheets that were easy to follow. The support we received from the CT team was first rate before, during and after each day’s ride. Accomodations were very good if not top of the line. The tour operators, Anne and Greg, are well-organized, friendly, and good companions on a ride. We will be repeat customers this Summer.
Carolina Tailwinds, hands down, is the best bicycle touring company anywhere. Their attention to detail and willingness to accommodate personal preferences are unsurpassed. Their routes are well-planned and the support and ability to deal with different riding levels…My wife and I have done nine tours with Carolina Tailwinds…We are veteran cyclists; if their tours were not really good, we would have never returned…we are going on our tenth this year.
We just signed up for our third tour with this excellent bike tour company. We fly from California just to go with Carolina Tailwinds. Their attention to every small detail is amazing. I think their personal attention as owners of the company is what makes the difference…really do care that each of their customers has the best possible biking vacation.
…The routes afforded beautiful scenery, and were well-supported…We especially liked the personal touch that Anne and Greg provided. They picked us up at our hotel; they kept a watchful eye on rider groups with a broad range of skills; and they hosted informal drinks and hors d’oeuvres each night before dinner…great exercise during the day and relaxing evenings with interesting people, comfortable lodging, and excellent meals.
Aside from knowing some of the most unique biking, lodging, and dining spots in the Mid-Atlantic area, Anne and Greg obviously love what they are doing…This husband and wife team is really tops when it comes to personal, friendly service and they excel in accommodating the needs of riders of all abilities…Our only complaint is that we never seem to lose any weight on their tours, but as they always remind us – “It’s a vacation, you’re not supposed to lose weight!” Looking forward to our fourth trip in four years with Carolina Tailwinds!
Trips are well planned and very well supported. The lodging chosen by the company suits the trips, are comfortable, and often unique. But the most notable item is the personal attention a rider receives throughout the trip. I’ve completed three trips with Carolina Tailwinds and have signed up for a fourth.
