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 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.


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!”












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 sucessful 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 instumental 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 remodling 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!