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

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Best of Madison Tour

6 Day(s)
Moderate
300 miles
avg 50 Miles
Guided

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 rol ...

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Door County Tour

6 Day(s)
Easy-Moderate
250 miles
avg 42 Miles
Guided

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 vi ...

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Colonial Virginia

6 Day(s)
Easy
225 miles
avg 38 Miles
Guided

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 ...

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Adirondacks & Vermont

6 Day(s)
Mod-Advanced
350 miles
avg 58 Miles
Guided

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 pl ...

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Middle Tennessee

6 Day(s)
Mod-Advanced
350 miles
avg 58 Miles
Guided

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 th ...

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Finger Lakes

6 Day(s)
Moderate
350 miles
avg 58 Miles
Guided

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 spec ...

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NC Horse Country

5 Day(s)
Mod-Advanced
300 miles
avg 60 Miles
Guided

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 ...

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Virginia Blue Ridge Tour

5 Day(s)
Mod-Advanced
300 Miles
avg 60 Miles
Guided

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 ...

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South Carolina Low Country

6 Day(s)
Easy
225 miles
avg 38 Miles
Guided

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 Stat ...

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Chesapeake Bay

6 Day(s)
250 Miles
avg 42 Miles
Guided

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 s ...

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Northern Shenandoah Tour

6 Day(s)
Mod-Advanced
350 Miles
avg 58 Miles
Guided

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 Massanutte ...

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Southern Shenandoah Tour

5 Day(s)
Mod-Advanced
300 miles
avg 60 Miles
Guided

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 agr ...

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Northern Outer Banks

5 Day(s)
Easy
200 miles
avg 40 Miles
Guided

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 ...

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Southern Outer Banks

6 Day(s)
Easy
Guided

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 lig ...

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