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

 Experience More...

Welcome l Our Tours l What to Expect l Pricing/Details l FAQ's l Contact Us

Carolina Tailwinds
The Best Bicycle Tours in 
the Carolinas, Virginia, Maryland, Delaware, 
New York, Tennessee, Florida, and Wisconsin!

The Ocracoke Lighthouse at sunset

Call us:

Visit us on Facebook


South Carolina Lowcountry Tour


Carolina Tailwinds is accepting employment applications for the 2017 tour season.

Click here if you are interested in joining our team.
Tour the famous Cape Hatteras Light on our Outer Banks Tours

CT Jerseys and ball caps available.  Click here to view.

Email us for details.


Email Newsletter icon Sign up for our Email Newsletter
For Email Newsletters you can trust



Take your pick between:

Tours in Hilly Terrain  or  Tours in Flat Destinations

South Carolina Lowcountry  6 days, 5 nights
   Flat bicycling, Delightful Cuisine   
   Late March & Late October  
Southern Outer Banks  
     Water all around: bike between it and ferry over it!  
     6-Day Version or a  4-Day Version
     April, May, October
Northern Outer Banks  5 days, 4 nights  
     Hatteras, Ocracoke, and Roanoke Islands
     Late April & Mid. October

Colonial Virginia  6 days, 5 nights  
     Jamestowne, Williamsburg, Yorktown...
     April, May, Sept., Oct.

Chesapeake Bay  6 days, 5 nights  
     Country roads, quaint villages and crabcakes!
     Early May & Early Oct.

NC Horse Country  5 days, 4 nights  
     Rolling country roads in the heart of NC 
      April, May, September, October

Middle Tennessee  6 days, 5 nights.  
     Hilly country bicycling in the the heart of the state
     April & September

Door County (WI)  6 days, 5 nights  
     Wisconsin's beautiful peninsula between the lakes

Best of Madison (WI)  6 days, 5 nights  
     Wisconsin's beautiful capital city and the rolling hills of the region

Finger Lakes  6 days, 5 nights  
     New York's rolling lake country
     July & August

Virginia Blue Ridge  5 days, 4 nights  
     Challenging road cycling in Virginia's western mountains

Southern Shenandoah  5 days, 4 nights    
     Best of the Blue Ridge and Alleghenies
     May & September
Northern Shenandoah
  6 days, 5 nights 
     Skyline Drive and surrounding valleys  
     Late May & Early September

Adirondacks and Vermont  6 days, 5 nights  
     Hilly bicycling in the Southern Adirondacks and SW Vermont

Florida First Coast  6 days, 5 nights  
     Flat road bicycling from Palm Coast, St. Augustine and Amelia Island

Visit our calendar page or individual tour pages for complete date listings.


"This was our 3rd bike tour, and by far the best.
Your company provides tours that are extremely 
well organized and attentive to the needs of the guests.  
We loved every minute of this tour--great biking, 
kayaking, food and people.  
Thank you for a fun and memorable trip." 
 -- Carrie, Rockville, MD


To join our mailing list,

click here

Carolina Tailwinds tours all offer:

  • bicycle vacations that balance physical activity and relaxation. 

  • comfortable inns in beautiful locations. 

  • the finest cuisine in each tour location.

  • companionship of like-minded travelers in a small group setting.

  • support, encouragement, and knowledge of local tour guides.

Be our guest and have a bike tour 
that will hook you on active travel for life!

Bicycling vacations for all Ability Levels


Welcome   |   What to Expect   |   The Tours  |   Pricing & Details   |   Contact Us
Who We Are
   |   FAQs   |  Online Reservation Form  |  Recommended Links  | Employment

  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