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Carolina Tailwinds
Contact Number:
International +1 336.794.1054
USA/Canada Tollfree +1 888.251.3206
PO Box 24716
Winston-Salem NC 27114-4716
Contact Tour Operator
Carolina Tailwinds

Carolina Tailwinds

Carolina Tailwinds leads multi-day bicycling vacation tours in the Eastern United States. All tours include the finest local cuisine and gracious lodging. Routes are fully supported with one or more vehicles and 2 or more professional bicycle tour guides.
Their Tours

Best of Madison Tour

6 Days Moderate 300 MLSAVG 50 MLS
Come see for yourself why this region is annually rated as one of the top ten bicycling destinations in the country! We start and end in Madison, a city which effortlessly blends big city culture with small town charm. Scenic lake views, miles of rolling terrain, a visit to Frank Lloyd Wright ...

Door County Tour

6 Days Easy-Moderate 250 MLSAVG 41 MLS
With the blue waters of Green Bay to the west and Lake Michigan on the north, east and south, Wisconsin’s Door County is a 75 mile long peninsula of dramatic limestone cliff faces, white sand dune lined lakeshores and abundant pristine water views. Interspersed through the splendid natural ...

Colonial Virginia

6 Days Easy 225 MLSAVG 37 MLS
Virginia's Lower Peninsula is rich in history: Home to the first successful English colony in America, the final dramatic battle of the American Revolution, numerous majestic James River plantation sites, and the incomparable living historic park that is Colonial Williamsburg. Bike routes on ...

Adirondacks & Vermont

6 Days Mod-Advanced 350 MLSAVG 58 MLS
Adirondack wilderness, verdant Vermont farmland, and the upper Hudson River Valley give the cyclist a lot to see in six days of cycling on this new tour. Covered Bridges, majestic views, quaint small towns and pristine lakes are just of few of the pleasures. Come join us as we explore some of ...

Middle Tennessee

6 Days Mod-Advanced 350 MLSAVG 58 MLS
Come ride the hills of the Volunteer State! Middle Tennessee is a beautiful area of rolling foothills and lightly traveled back roads. Known for the Home of Country Music and the Jack Daniels Distillery, there is a lot more for the road cyclist to savor along the way.

Finger Lakes

6 Days Moderate 350 MLSAVG 58 MLS
The highest waterfalls east of the Rockies, cascades, glens, colleges, hamlets, valley farms, quaint towns and steep hillsides dotted with vineyards. All of this, in addition to the sparkling waters of long blue lakes, make the NY Finger Lakes a special bicycling destination not to be missed ...

NC Horse Country

5 Days Mod-Advanced 300 MLSAVG 60 MLS
The moderately hilly region found in central North Carolina is one of the state's best kept secrets for perfect cycling conditions! Peaceful country back roads wind past peach tree groves, scenic thoroughbred horse farms, remote Revolutionary War historic sites, world renowned pottery studios ...

Virginia Blue Ridge Tour

5 Days Mod-Advanced 300 MLSAVG 60 MLS
Exhilarating road biking, exquisite dining, and spectacular mountain scenery await you in the remote northwest corner of North Carolina. You'll bike the famous Blue Ridge Parkway with its majestic views of the surrounding mountains. Also leave the main routes behind as we guide you on little ...

South Carolina Low Country

6 Days Easy 225 MLSAVG 37 MLS
This tour packs the best of the South Carolina Low Country into a fabulous 6 day multi-sport vacation. Bike the idyllic islands of the South Carolina coast under stands of live oaks and wispy Spanish moss. Learn about the history of the Palmetto State's plantation past. Walk the beaches with ...

Chesapeake Bay

6 Days 250 MLSAVG 41 MLS
In a region defined by the numerous exquisite tidal rivers that drain into the Chesapeake Bay and the shimmering beauty of undeveloped seashore on the Atlantic Ocean, miles of flat coastal cycling await you. Views of rural farmland, Chesapeake Bay skipjacks and sailing craft, fishing boats, and ...

Northern Shenandoah Tour

6 Days Mod-Advanced 350 MLSAVG 58 MLS
Apple orchards, equestrian estates, and the numerous overlooks of Skyline Drive provide the setting for this tour for bicycling enthusiasts. Several great climbs punctuate our tour through the countryside of northern Virginia. We'll tackle Massanutten Mountain, a long ridge that bisects the ...

Southern Shenandoah Tour

5 Days Mod-Advanced 300 MLSAVG 60 MLS
Breathtaking Blue Ridge overlooks, pastoral valley farms, and winding mountain passes provide the setting for this incredibly diverse tour. Jagged Alleghenies on the west and the awesome Blue Ridge on the east define the boundaries of the fertile agricultural Shenandoah Valley. Farm roads ...

Northern Outer Banks

5 Days Easy 200 MLSAVG 40 MLS
Hatteras, Ocracoke, and Roanoke Islands are all featured on this itinerary that allows the bicycle tourist to explore more of the Outer Banks. Visit the site of the Wright brothers’ first flight, miles of undeveloped seashore, up to four historic lighthouses, and more. Enjoy fresh local ...

Southern Outer Banks

6 Days Easy
Sparkling sandy beaches, delectable seafood, relaxing ferry rides, and extraordinary biking await you on this special tour. We visit in the spring and fall, when the crowds are gone and the weather is perfect for bicycling. The famous picturesque lighthouses of the North Carolina seashore ...

While great care has been taken to show full and correct tour details, Cycle Tours Global does not take responsibility for any errors or ommissions. Plans or bookings should not be made exclusively based on information shown on this website but must be confirmed with the tour operator.