Our Story
All of our destinations have been selected after long personal experience and research. We have known them well for many years and are eager to share them with you. We have selected routes, inns, and dining that reflect the uniqueness of each area we visit. Each of these important features will leave you with a lasting impression and rewarding memories.
We have grown our destinations slowly over the years. Some take a season or a few off, then come back improved and better than ever. Each new trip follows our time tested model — focusing on great cycling routes, memorable inns, and great food. We only offer tours that our team can lead — we do not outsource tours to other companies.
Our Team
Carolina Tailwinds has been owned and operated by Anne & Greg Fleming since its inception in 2001. Over several years, we have been lucky to find a few good men and women who share our values and make our little team better. In addition to Anne and Greg, Jeff, Jerry, Mike, Trish, Paige and Tom are guides that you may get to meet in 2024. Each brings enthusiasm, organizational skills and interesting perspectives on life to each tour. Each is trained in first aid and C.P.R. and meets all of the qualifications to drive commercial motor vehicles. Our guides are here to make your cycling vacation an experience to savor for years.
Mitch keeps the bikes in top shape, manages the warehouse, and supervises the turnarounds of equipment and supplies.
We are ready to roll again in 2024!
Meet the team:
Jeff Lovett
Be it whitewater canoeing, hiking, sailing, sea kayaking, or cycling, Jeff’s passion is enabling individuals to celebrate their physical fitness through outdoor adventures. Jeff has worked as an outdoor educator and guide since 1993. When not on two wheels, Jeff pours his energy into the repair, refit, and restoration of sailing and motor yachts. He will be happy to talk about bikes, boats, or just about any other topic. Jeff guides most often in Door County WI, SC Lowcountry, Chesapeake Bay, Colonial Virginia, and New York Finger Lakes.
Jerry Nutt
Jerry is retired from computer sales and lives in Huntsville, AL. A leader and organizer of bike rides of all kinds at home, Jerry also works part-time in a local bike shop. Gifted at keeping things light, he may break into song if needed. Jerry most frequently leads our Adirondacks and Vermont, Middle Tennessee, and Georgia Historic Heartland tours.
Trish Haitz
“I like being a bike guide because it blends many of my passions. As an educator, watching people explore new areas gets me so excited. Then add a bicycle to that! Riding a bicycle has always meant freedom to me.” Trish calls a 25 ft sailboat named Yankee Girl home. When not working as a bike guide or an Outward Bound instructor, you’ll find her working on her sailboat or exploring the world on her gravel bike. She doesn’t own a t.v. “My favorite CT Tour is Door County! I enjoy the small towns, the food, and maritime environment we travel through. Door County is also very bike friendly. Few cars and nice roads!”
Keith Nance
Keith is a semi-retired pathologist who lives in Raleigh, where he commutes to work by bike. A lifelong avid cyclist and triathlete, Keith loves riding on the Blue Ridge Parkway and country roads of the NC High Country. Recently Keith has become active in his local community repairing and distributing donated bikes to the needy and advocating for better cycling conditions. He most frequently guides our Southern Outer Banks, Shenandoah and VA Blue Ridge Tours, among others.
Michael O’Donnell
Michael has found joy in bicycling his entire life! After a long career in corporate finance, he found his true calling as a bicycle tour guide and has guided tours for Carolina Tailwinds since 2011. His joy for cycling extends to sharing destinations, experiences and fun with all of our fascinating guests. He is our lead guide on the NC Outer Banks, and also works NY Finger Lakes and others. His favorite tour is whatever one he is currently guiding! The NC Outer Banks are a long-time favorite riding destination for Michael, however, all of our tours in up-state New York, Virginia, Vermont and western North Carolina also stand out for him due to the challenging routes, natural beauty and relaxing culture. Michael hails from Raleigh, NC where he enjoys global travel with his wife Amy, collecting classic cars and, of course, cycling!!
Tom Williams
New to the team in 2022, Tom has 20 years of small business ownership behind him. A former baker for a very successful bakery in Cary, NC, Tom embodies attention to detail and quality control. Support vans don’t stay dirty long when Tom is around. Now living in Deep Gap, NC, Tom’s favorite ride is the nearby Blue Ridge Parkway.
Paige Williams
Paige (married to Tom) also brings their shared small business acumen to every tour. A master of customer service, we are lucky to have Paige’s eyes and ears on our tours. Paige and Tom are parents of 4 grown children and also have a passion for volleyball.
Wilder Boule
Wilder is a longtime bicycle tour guide and has been with Carolina Tailwinds since 2013. In addition to guiding for us, Wilder has been instrumental in designing our Middle Tennessee, Michigan Cherry Coast, and Door County WI tours, and designing our custom jerseys. He is actively involved in raising his two kids and works in home remodeling as well.
Anne Fleming
Anne was a C.P.A. who discovered 20 years ago that she would rather be helping others enjoy the great outdoors. In addition, Anne loves to try new recipes in the kitchen and spend time with her nephews.
Greg Fleming
Greg is happier outside, whether it is on a bike, footpath, or just pulling weeds in the yard. If he has to be indoors, he is Anne’s dutiful sous chef and chief sanitation officer, and hopefully there is a Duke basketball game on!
