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.
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Trip Overview
Price
- Early bird discount: $2895 per person
- Full price: $2995 per person
- Single room supplement: $625
Upcoming tour dates & status
- 6/1/25 – 6/6/25
- 6/8/25 – 6/13/25
- 9/14/25 – 9/19/25
- 9/21/25 – 9/26/25
Meeting/Departure Point
Downtown Cincinnati
Nearest Airport
CVG: Cincinnati/Northern Kentucky International
Duration
6 days, 5 nights
Tour difficulty
Mostly Flat Terrain
Included
Tour prices are per person rates and include all of the following:
- Lodging costs (double occupancy rooms), including all taxes/fees
- All breakfasts and most lunches
- All dinners described in the tour itinerary. Please note: alcoholic beverages are not included
- Morning and afternoon snacks
- Route planning and detailed daily area maps
- 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 were 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 photo cd of your tour on request
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
20–41 miles, flat, easy terrain
Embark on an unforgettable 41-mile bicycle trail ride that begins in Cincinnati, Ohio, and takes you through the scenic landscapes of the Little Miami Scenic Trail, which is part of the popular Ohio to Erie Trail system. This day of cycling winds through southern Ohio including the charming town of Loveland and ending in historic Lebanon Ohio. This ride combines natural beauty, and a dash of history. As you journey along the peaceful riverside path, you’ll enjoy lush greenery, quaint bridges, and vibrant small towns. Our destination is the historic Golden Lamb Hotel in Lebanon, Ohio, a beloved landmark dating back to 1803 and has hosted 12 U.S. presidents, politicians, and literary greats such as Samual Clemens and Charles Dickens. Here, you can unwind, savor a delicious meal, and immerse yourself in rich Ohio history.
Day 2
33–56 miles, flat, easy terrain
Day 2 of our Ohio bicycle tour promises another exciting adventure on the Ohio to Erie Trail! After a brief 20-minute shuttle, you’ll start pedaling through scenic Ohio landscapes, with options to ride between 33 to 56 miles to suit your pace and preference. The day’s route is filled with gentle stretches and scenic views, leading to the Xenia Trail Hub, a popular gathering spot at the heart of Ohio’s bike trail network. Here, you’ll enjoy a relaxing picnic lunch, refueling amid the beautiful park scape, and optional trail riding to make the most use of Ohio’s vast bikeways.
Day 3
25–48 miles, flat, easy terrain
Day 3 of our Ohio bicycle tour takes us west from Lebanon to Middletown, where we’ll begin a scenic 25-mile ride along the Great Miami River. This morning’s route brings us to the historic Carillon Park in Dayton, home to the U.S. National Park monument dedicated to the Wright Brothers’ first airplane—a true tribute to Ohio’s aviation legacy. After exploring the museum and enjoying lunch, we’ll set out for another 23 miles on the trail, winding our way to the lively and eclectic town of Yellow Springs. Known for its unique shops, vibrant arts scene, and small-town charm, Yellow Springs is the perfect place to unwind after a day of memorable rides and discoveries.
Day 4
39–39 miles, flat, easy terrain
We embark on a picturesque 39-mile ride, departing from the charming town of Yellow Springs and connecting to London, Ohio, along the Ohio to Erie Trail. This stretch of the trail follows an old rail line, leading us through historic rail towns that offer glimpses into Ohio’s past. The path is lined with scenic countryside, rustic bridges, and traces of the region’s railway heritage, creating a journey that’s as beautiful as it is nostalgic. Whether you’re a history buff or simply love scenic cycling, this ride offers a perfect blend of culture and nature on one of Ohio’s most treasured trails. After lunch there is an option to cycle all or part of the way back to Yellow Springs.
Day 5
25–25 miles, flat, easy terrain
After a quick shuttle from Yellow Springs to London, Ohio, you’ll start a 25-mile ride from the London Prairie Trailhead, following the Camp Chase Trail into the heart of Columbus. This stretch is filled with beautiful views of Ohio’s farmland and peaceful wooded paths, leading you right into the vibrant capital city. Once in Columbus, you’ll have the option to add extra miles exploring the Scioto and Olentangy trails or to spend the afternoon off the bike, soaking in Columbus’s rich arts, food, and cultural scene. It’s a day that balances the thrill of riding with the opportunity to discover the sights of Ohio’s largest city.
Day 6
10–25 miles, flat, easy terrain
On the final morning of our Southern Ohio cycling tour, we’ll enjoy a beautiful ride through Columbus’s extensive trail network. Starting along the scenic Scioto River, we’ll connect to the Alum Creek Trail, surrounded by lush greenery and creekside views, offering a peaceful and fitting end to a week of exploration on Ohio’s trails. This last stretch provides a chance to savor the sights and sounds of Columbus before we gather for a celebratory lunch, reflecting on the incredible journey we’ve shared. It’s the perfect finale to an unforgettable week of adventure and camaraderie on Ohio’s finest trails.
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
Night 1 & 2
The Golden Lamb, Lebanon, OH: A stage coach inn constructed in 1803, the Golden Lamb has never lost sight of its roots as a hotel. Today, the hotel mixes modern amenities with antiques and Shaker décor. Located on the top three floors, each one of the 17 historic overnight rooms features stunning antique furnishings, new Tempur-Pedic mattresses, private baths, television and air conditioning. Note: this historic inn does NOT have an elevator, and all rooms are on floors 2 – 4.
Nights 3 & 4
The Mills Park Hotel offers 28 tastefully decorated rooms in the heart of charming Yellow Springs. Onsite dining and common space make it the perfect place to relax and socialize. Rooms feature luxury linens, Smart TVs, custom solid wood desks, armoires, and upholsteries. Internet access, coffee makers, and hair dryers are standard features in all rooms. Enjoy the exceptional quality of custom Amish hand-crafted furniture and pillow top mattresses.
Night 5
Our Columbus hotel is historic on the outside and modern on the inside with sweeping veiws of the the downtown skyline. We will be walking distance to restaurants and shopping.
Get Prepared!
Cycling
The terrain is mosty flat. Mileage each day will range from 25 – 56+ miles, at your option. As with all Carolina Tailwinds tours, you can take advantage of the support van to “leap frog” ahead on the route.
All of the routes are on paved rail trails, with a few short section on side streets.
Tour Point of Origin for Complimentary Day 1 Shuttle:
Columbus, OH airport area (John Glenn International/CMH), with a complimentary shuttle to Smale Park, downtown Cincinnati.
Tour Point of Origin for those hiring their own ground transportation:
Smale Riverfront Park, downtown Cincinnati.
Getting to the Tour Start (Columbus, OH)
Airports:
John Glenn International (Columbus) (CMH) https://flycolumbus.com/
Service by 11 airlines to 50 non-stop destinations. This tour ends in Columbus. We will offer ground transportation at specific time on the first day of the tour from the Columbus airport area to Cincinnati.
Cincinnati/Northern Kentucky International (CVG) https://www.cvgairport.com/
Service by 12 airlines to 55 non-stop destinations. You may want to consider flying into CVG at the beginning of the tour. We would still recommend flying home from CMH at the end of the tour. Carolina Tailwinds will NOT provide any shuttles to or from CVG, so you will need to make your own ground transportation plans if you use this airport.
Ground Transit:
Carolina Tailwinds will provide a courtesy shuttle from CMH and CMH airport hotels to downtown Cincinnati early on the morning of the first day of the tour. Carolina Tailwinds will provide a courtesy shuttle back to CMH and CMH airport hotels on the afternoon of the last day of the tour.
At all other times, taxis, Ubers, limos, and rental cars are available at CVG and CMH.
Parking: You may want to consider parking at a CMH airport hotel or at this parking facility:
https://www.thefastpark.com/
Carolina Tailwinds can include this location in its courtesy shuttles mentioned above.
NOTE: If you drive to Cincinnati at the beginning and park your car there, you will need to arrange your own transportation back on the last day.
Arrival/Departure Timing
In order to participate in the Day 1 meeting and bike ride, please plan to arrive in the Columbus airport area no later than 8:30 a.m. If you are arranging private transportation to Smale Park in Cincinnati, please be there by 11:30. (10:30 a.m. if renting a bike).
On Day 6, we will conclude in Columbus between 12 and 1:00 pm. Flight timing on our last day should not be booked any earlier than 4:00 p.m. from CMH.
Extend Your Vacation
Before or after our activity packed tour, you may want to tack on a few days.
Columbus: Experience attractions like the Columbus Zoo & Aquarium or Franklin Park Conservatory and Botanical Gardens. Don’t miss the National Veterans Memorial and Museum, the only museum of its kind, COSI, voted best science museum in the nation three times by USA Today’s 10Best awards, and the Columbus Museum of Art.
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?
Ride the famous Ohio bike trails from Cincinnati to Columbus, showcasing the best cycling routes in the state
Explore historic towns like Lebanon and Yellow Springs, known for their rich heritage and vibrant communities
Explore charming towns like Ticonderoga and Brandon, providing perfect opportunities for memorable stops and photo ops along the way
Visit the Wright Brothers Museum in Dayton and discover the birthplace of modern aviation
End your journey with a peaceful ride on the Alum Creek Trail, surrounded by lush greenery and riverside views
See What Our Customers Say About Us
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.
…‘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.
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.
