Carolina Tailwinds

Carolina Tailwinds

Carolina Tailwinds offers bicycle vacation tours in beautiful locations throughout the Eastern U.S.A. With trips from 2 to 6 days, several can be combined to create a longer bike vacation in the region. Accommodations are historical inns and B & B’s. Great value … a week with Carolina Tailwinds is about 1/3 of the price of most Tuscany tours! You’ve got to love a company that mentions lemon soufflé pancakes and shrimp and mushrooms cappellini with sherry sauce on their FAQ page!

Regional Notes:

usa - NC, VA, MD

Leave A Review


19 Reviews

  1. Catherine La Fleur, Milwaukee WI-Reply
    November 5, 2021 at 3:21 pm

    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.

  2. Mike Carmody, Webster NY, USA-Reply
    July 22, 2020 at 12:11 pm

    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.

  3. Mike Jones Meadows Place Tx-Reply
    October 20, 2019 at 2:26 am

    Tell me about some of your 2 day tours
    Location and cost.
    Anything in the Jamestown Va area?

  4. Julie and Doug Atlanta-Reply
    June 2, 2019 at 11:27 pm

    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.

  5. Lil and Laura, State College, PA-Reply
    November 3, 2017 at 11:10 pm

    We are two retired friends who left our non-cycling husbands at home to have a biking adventure. We throughly enjoyed our Florida tour. It was a total vacation with Anne and Greg attending to every detail. The biking was amazing – route cards made navigation easy and guided us along beautiful paths and roads that felt safe. Although it seemed we were on our own, our guides were at our backs to provide snacks, sun screen, and any assistance needed (even sunglasses). The bikers we rented from CT were fitted to us and were maintained in perfect condition throughout the trip. Ditto all comments about the food and lodging, FIRST RATE! We’re ready to book another CT trip!

  6. Christine S., Rush, NY-Reply
    September 29, 2017 at 7:15 pm

    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. 

  7. Lany ciccone Boston, ma-Reply
    August 14, 2017 at 12:59 am

    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.!

  8. Finger Lakes, NY-Reply
    August 9, 2017 at 6:20 pm

    Fabulous week of challenging rides through exceptional scenery. Having been on several other bike companies’ tours I have a good perspective to highly recommend Carolina Tailwinds. We had a group of 16 cyclists (several were repeat CT clients) of varying abilities and Greg and Anne, the CT owners, along with our 3rd guide, John, managed the the entire week very well. They were perfectly organized, personally knowledgeable of the routes, and prepared for everything we wanted or needed for a great week.

    The hotels CT chose were superb along with their meals and in one instance, the 3-piece bluegrass band. Both Watkins Glen and Skaneateles are marvelous towns to explore. The walk up the falls in Watkins Glen is a must do (walkway with steps).

    Each day we were presented with 2 to 3 routes of different lengths and profiles. We could choose at the beginning or at diverging points along the way with all routes covered by either the 2 vans or a cycling guide. CT’s maps and cue sheets were spot on.

    CT provided bikes to many of us. Mine was a Lapierre carbon/105 which performed perfectly.

    If you take on challenges and won’t stop until you’re done, CT’s Finger Lakes tour has the hills and distances you’ll love. If you’d rather roll along lake views and end at a vineyard tasting room (after all, this is the New York wine country), CT has van support and route layouts to tailor your 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.

  9. Scott E., Richmond, Va-Reply
    November 1, 2016 at 5:21 pm

    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.

  10. Ernie Precious, Devon, PA-Reply
    November 1, 2016 at 5:21 pm

    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!

  11. M. Riedinger, Huntington Bay, NY-Reply
    November 1, 2016 at 5:20 pm

    My wife and I are dedicated cyclists, and we wanted a trip that was oriented around climbs. We took Carolina Tailwinds’ Blue Ridge tour and the ride was a real challenge, but no sagging was required. 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.

  12. Jim Grattan, Atlanta, GA-Reply
    November 1, 2016 at 5:20 pm

    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 are just right. Greg and Anne make a special effort to get to know every one on their tours. The B&Bs that they select are always top notch. Along with their service, their tours are probably the best priced. My wife and I have done nine tours with Carolina Tailwinds as of 2008, both mountainous and sea coast. We are veteran cyclists; if their tours were not really good, we would have never returned for even one. As it stands, we are going on our tenth this year.

  13. Bill and Patti Van Orden, Templeton, CA-Reply
    November 1, 2016 at 5:20 pm

    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. They have both been on the two previous tours we have gone on, and although they have now expended (because of popularity I suspect) to the point they now have hired staff to assist them, at least one of them will be accompanying every tour. This is the difference. They are the owners and really do care that each of their customers has the best possible biking vacation.

  14. Tina and Brent West, Yarmouth, ME-Reply
    November 1, 2016 at 5:19 pm

    We have enjoyed two vacations with Carolina Tailwinds. … The routes afforded beautiful scenery, and were well-supported by the Flemings. 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. We got the vacation we wanted: great exercise during the day and relaxing evenings with interesting people, comfortable lodging, and excellent meals.

  15. Matt & Maggie Lechowicz, Hagerstown, MD-Reply
    November 1, 2016 at 5:19 pm

    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, and it shows in Carolina Tailwinds tours. 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. We really have enjoyed their multi-sport tours which accent the biking with a day of hiking or kayaking. 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!

  16. K. Yarnell, Tampa, FL-Reply
    November 1, 2016 at 5:19 pm

    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.

  17. Ted T., Greensboro, NC-Reply
    November 1, 2016 at 5:18 pm

    As the name hints, this ‘company’ leads tours mainly in the SE US, including the Delmarva peninsula. ‘Company’ is misleading: this is a personal experience. Anne and Greg Fleming are energetic cyclists themselves who are present and conduct each trip. As someone who used to arrange his own multi-day self-supported bike tours, I tried outsourcing the effort to Anne and Greg, and, once spoiled, I’ve not taken to the road on my own since. 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’m probably their unusual client: a guy who likes to pedal 60-100 miles/day. But they must see my kind fairly often, as well as the client who wants to do 20 mi., then get in the van. I’ve been on 3 different trips with them now, and all cycling agendas have been represented and handled on each trip.

  18. Susan affalter, Allison Park-Reply
    November 1, 2016 at 5:18 pm

    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.

  19. Kent Billingsley, Carol Stream, IN-Reply
    November 1, 2016 at 5:18 pm

    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.

  20. K Nance, Raleigh, NC-Reply
    November 1, 2016 at 5:17 pm

    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.

  21. Leon & Lucille W.-Reply
    November 1, 2016 at 5:17 pm

    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.