Bicycle Tours by Carolina Tailwinds

Carolina Tailwinds offers bicycle vacation tours to seven beautiful locations 
in North Carolina, Virginia & Maryland.  

A bicycle tour of North Carolina's southern Outer Banks:

Flat coastal bicycling, sparkling sandy beaches, delectable seafood, relaxing ferry rides, and extraordinary biking await you...

A bicycle tour of North Carolina's northern Outer Banks:

Easy bicycling, placid canoeing, fine dining, and luxurious accommodations welcome you to the Northern Coastal region of North Carolina...

A 2-day bicycle tour of the Yadkin River Valley of NC:

Enjoy a perfect blend of activity, local wines and fine cuisine on our weekend getaway to North Carolina's beautiful wine country...

A multi-sport tour of the highlands of Virginia and North Carolina:

Want to bike in the mountains but don't want to climb hills?  Then this tour is for you! Our Virginia Rail Trail Tour is designed to...

Blue Ridge Tour
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A more challenging road bicycling tour of the Blue Ridge Mountains, including the famous Blue Ridge Parkway.

The northwest corner of North Carolina provides one of the most visually rewarding and genuinely hospitable  areas of our state...

Southern Shenandoah Tour
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A more challenging road bicycling tour of the Southern Shenandoah Valley, Allegheny Mountains and Blue Ridge Parkway.

Breathtaking Blue Ridge overlooks, pastoral valley farm roads, and winding mountain passes provide the setting for this incredibly diverse tour...

Northern Shenandoah Tour (NEW!)
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A more challenging road bicycling tour of the Northern Shenandoah Valley, Massanutten Mountain, and Skyline Drive.

Apple orchards, equestrian estates, and the numerous overlooks of Skyline Drive, provide the setting for this tour for bicycling enthusiasts...