Embark on a captivating journey through Georgia’s Historic Heartland, where equestrian farms, lakes, and rolling hills await. Starting in the vibrant city of Athens, known for its cycling culture and home to the University of Georgia, our tour leads you through picturesque countryside and charming small towns.
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.
Click the tabs to find out more
Trip Overview
Price
Early bird discount: $2710 per person
Full price: $2810 per person
Bicycle rental : $100
Single room supplement: $625
Rooms with two beds are only available on nights 1 and 2 of this tour. Therefore, solo travelers will automatically have private rooms on nights 3 and 4.
Upcoming tour dates & status
- 4/27/25 – 5/2/25
- 10/12/25 – 10/17/25
Meeting/Departure Point
Nearest Airport
ATL Hartsfield-Jackson Atlanta International
Duration
6 days, 5 nights
Tour difficulty
Gently rolling to moderately hilly
Included
- Lodging:
5 nights lodging: 3 at Hotel Indigo and 2 at the
James Madison Inn. - Meals:
Dinner on nights 1 & 4; all lunches except 1; all breakfasts; snacks; and hors d’oeuvres most nights. - Full Route Support & Luggage Transfer:
Service of 1 – 2 support vans on route every day.
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
5–20 miles, rolling hills
Athens is the quintessential college town, as well as a progressive cycling community. Well underway is an ambitious plan of paved bike trails, including the North Oconee River Greenway and the Firefly Trail. Dominated by the University of Georgia campus, Athens has a pleasant, artsy vibe. Unique local restaurants and shops line Clayton Street, Broad Street and others for block after block. The UGA campus definitely deserves a visit. Walk through the famous Arch to see a beautifully landscaped campus with buildings dating back to 1806.
We’ll have bike fittings, orientation and lunch at our upscale hotel in the heart of downtown. Afterwards we’ll enjoy a bike ride in and around town and campus to see a few of the spots that make it unique. Afterwards we’ll enjoy getting to know each other at a private event space downtown.
Day 2
25–51 miles, moderate rolling hills
We’ll ride from downtown Athens to the community of Winterville. The two communities are now connected by the Firefly Trail. That launches us onto a wonderful bike ride into the surrounding countryside. The route over gently rolling terrain will take us across the longest covered bridge in Georgia, and ultimately back through Winterville.
Day 3
25–57 miles, moderate rolling hills
After breakfast at the hotel you will have the option of commencing today’s ride from there, or taking a quick shuttle out of town to start riding in the Georgia countryside. Today’s route will include lovely country and quaint crossroad communities. One version of this route was named the best route in Georgia a few years ago.
Back in Athens for a second night, you have time to explore downtown and the UGA campus. We recommend trying a flight at Creature Comforts Brewing Company, a successful local brewery. Dinner will be on your own this evening, with plenty of options within walking distance of the hotel. Athens has become a true foodie town, with restaurants such as The National and Last Resort Grill earning an excellent reputation.
Day 4
35–56 miles, moderate rolling hills
We leave Athens behind today, heading south through a combination of farmland and forest. You’ll get to bike across another historic covered bridge on the way. Our ultimate destination is the stunningly beautiful town of Madison. Founded in 1809 as the county seat of Morgan County, it was named for James Madison, who was inaugurated as the 4th U.S. President two months prior. Saved from destruction during the Civil War by a Union sympathizing mayor, Madison has a remarkably intact and well-maintained inventory of antebellum homes and business structures. Madison has been called “one of the 50 most beautiful small towns in America” by Architectural Digest, and “one of the South’s prettiest small towns” by Southern Living Magazine. Our lodging for two nights, the James Madison Inn sits across from a town park, and nearby streets are lined with restaurants and boutique shops.
Day 5
23–54 miles, moderate rolling hills
Our layover day in Madison provides multiple cycling route options, so you can choose the distance that appeals to you. Some of the prettiest scenery of the tour may exist in this area south, east and west of town. Numerous equestrian estates dot the landscape. The small former railroad town of Rutledge has a few charming shops and cafes, but mostly the ride will be in rural countryside.
Day 6
25–51 miles, moderate rolling hills
Our last day takes us back to Athens. Yet another day of pleasant cycling on smooth and scenic Georgia roads awaits. We’ll bike through sleepy crossroads communities of Bostwick, filming site of hilarious scenes in “My Cousin Vinny,” and Bishop before reaching Watkinsville, just south of Athens. We’ll get you back to your car in time for a late lunch, showers and departure.
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 & 3
Hotel Indigo, Athens, GA
Hotel Indigo Athens elevates the downtown cityscape with our modern farmstead architectural style. Pairing Southern hospitality with a deep appreciation for local culture, this boutique retreat charms worldly travelers, music aficionados, and trend-setters with its high-end service and chic, art-centric spaces.
Nights 4 & 5
The James Madison Inn
Located in historic downtown Madison, The James Madison Inn and Conference Center is within walking distance of antebellum homes, graceful parks, stellar shops, art & antique galleries, spas and fine restaurants. It is elegantly appointed and offers a unique, luxurious way to experience Madison. Seventeen rooms and two suites in this boutique hotel set the stage for luxurious Southern hospitality. With paintings of landmarks, custom furniture and peerless service, the inn brings local lore and Southern charm to life for guests.
Get Prepared!
Cycling
The terrain is rolling hills. This generally equates to 1,500 – 2,000 feet of climbing on a 30-40 mile route. Mileage each day will range from 25 – 55+ miles, with multiple options available. 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 country back roads or busier roads with bicycle accommodation, and the scenery is beautiful, including well-maintained farms, equestrian estates, and forest.
Tour Point of Origin
Hotel Indigo, 500 College Ave, Athens, GA 30601
Getting to the Tour Start (Athens, GA):
Driving: Approximate travel distance to Athens–
- Atlanta, GA: 72 miles
- Augusta, GA: 94 miles
- Savannah, GA: 219 miles
- Greenville, SC: 94 miles
- Jacksonville, FL: 341 miles
Airports:
Hartsfield-Jackson Atlanta International Airport (ATL) www.atl.com/
Service by all major airlines (75 miles from tour start/end location).
Greenville Spartanburg International Airport (GSP) www.gspairport.com
Service by Allegient, American, Delta, Southwest & United (105 miles from the tour start).
Ground Transit:
Groome Transportation offers a shuttle between ATL to Athens that makes 10 round trips daily. Reserve online at https://groometransportation.com/athens/ or call: (706) 612-1155. athensoffice@groometrans.com
Rental cars, Uber, and limos are available at Atlanta (ATL) and Greenville (GSP).
Parking: We have arranged for long term parking there for the duration of your tour.
Arrival/Departure Timing
In order to participate in the Day 1 meeting and bike ride, please plan to arrive in Athens no later than 11:30 a.m. (10:30 a.m. if renting a bike).
On Day 6, we will return to Athens between 12 and 1:00 pm. Flight timing on our last day should not be booked any earlier than 5:00 p.m. from Atlanta.
Extend Your Vacation
Before or after our activity packed tour, you may want to tack on a few days.
Athens: This vibrant college town has plenty to explore.
- The State Botanical Garden of Georgia is just south of town and boasts 313-acres of themed display gardens, including the Flower Garden, the International Garden, the Heritage Garden, the Shade Garden, and 5 miles of nature trails.
Note: Athens is home to the 92,700 seat Sanford Stadium, home to the 2021 National Champion Georgia Bulldogs Football Team. On home football game weekends, lodging is scarce or non-existant and extremely expensive. On those weekends, you may want to choose lodging near the Atlanta airport if flying, or in another community in the region if driving.
Bulldogs schedule: https://georgiadogs.com/sports/football
Atlanta, GA: https://discoveratlanta.com
- The Georgia Aquarium https://georgiaaquarium.org
- World of Coca Cola https://www.worldofcoca-cola.com/
- Guided bicycle tours of Atlanta https://biketoursatl.com/
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?
Bike through historic covered bridges and charming countryside
Explore the vibrant college town of Athens, home to the University of Georgia
Enjoy scenic routes through picturesque rural landscapes
Experience the beauty and tranquility of Madison, one of America’s most beautiful small towns
Indulge in local dining and brewery experiences in Athens and Madison
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.
