Carolina Tailwinds l Northern Outer Banks Bicycle Tour Bicycle Vacations in the Eastern U.S.A. 

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The Carolina Tailwinds Team 

            We had some specific goals when we started Carolina Tailwinds in 2001: to share our love of active touring, to focus on personalized service, and to form long-term relationships with our guests.  It has been very rewarding to see our tour approach validated by our customers' through their repeat business and tour evaluations!

            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 been fortunate to grow our destination base the last few years with 7 new trips added between 2013 and 2016.  Each new trip follows our time tested model -- focusing on great cycling routes, memorable inns, and great food.

            Over the several years, we have been lucky to find a few good men and woman who share our values and make our little team better.  They are ready to roll again in 2016!

Wilder Boule

Mary Fingeroff

John Gray

Trish Haitz


Joe Jacaruso Mike O'Donnell Carl Karpinski


We hope this website is useful to you, but don't assume that we don't want to talk to you.  We welcome your phone call and are always happy to talk about cycling.  Please call us with any questions you may have.  Our toll free number is 888.251.3206 (local number is 336.794.1054).    We look forward to hearing from you and hope to tour with you soon.

Anne & Greg Fleming

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  Carolina Tailwinds, Inc.  "Carolina Tailwinds" and the Carolina Tailwinds Logo are Service Marks of Carolina Tailwinds, Inc.

Carolina Tailwinds   P.O. Box 24716   Winston-Salem, NC 27114-4716   888.251.3206 or 336.794.1054