Carolina Tailwinds
Fully supported inn-to-inn bicycle tours in 10 states throughout the Eastern U.S.
Their goals on starting Carolina Tailwinds in 2001: to share their love of active touring, to focus on personalized service, and to form long-term relationships with guests.
It has been very rewarding to see our tour approach validated by our customers through their repeat business and tour evaluations!
We offer the best value in the industry. For starters, our guest to guide ratio (never over 7:1) is unbeatable. Our easy date change/cancellation policies give you peace of mind. More is included in our tours so that you won't be surprised later: almost all meals are included (usually all but one), and we let you order from the menu at dinner, rather that limiting you to one or two choices. Extra activities such as paddling are usually included on each tour, not given as options to discover on your own. If we call a tour a 6-day tour, then there is a guided activity on all 6 days -- we don't charge for "arrival days." As a courtesy, we take photos for you throughout your tour and send you online access after the tour is over. You won't be receiving piles of fancy catalogs from us each year--we keep our overhead low is by growing slowly through client referrals and repeat business. We spend your money on your vacation.
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.
New York Finger Lakes Tour
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
344 mi (~57mi per day)
Active
Hilly, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
A Six Day Cycling Vacation of the Finger Lakes Region in Upstate New York
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 glacial lakes, make the NY Finger Lakes a special bicycling destination not to be missed.
Georgia's Historic Heartland
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
289 mi (~48mi per day)
Active
Some hills, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
Bicycle Tour of Athens, UGA, and Madison, GA
An Inn-to-Inn Cycling Tour of Georgia's Rolling Heartland
Athens, GA is home to the University of Georgia and is a cycling hotbed. Madison, GA has been called "one of the 50 most beautiful small towns in America" by Architectural Digest, and "one of the South's prettiest small towns 2018" by Southern Living. We have designed this tour to focus on rural inn-to-inn routes, keeping van shuttles to an absolute minimum.
South Carolina Low Country
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
225 mi (~38mi per day)
Leisure
Mostly flat, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
Bike Tour of Charleston, South Carolina's Lowcountry
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 gentle sea breezes and stroll past architectural treasures on the streets of Charleston and Beaufort, SC. And, of course, experience the legendary warmth and charm of southern hospitality in gourmet restaurants and cozy inns.
The terrain is flat, making it accessible to all ability levels. Strong coastal winds sometimes present a minor challenge, but they are just as likely to propel us along our route! Along the way, observe coastal wetlands and rural farmland as we bike the scenic back roads of South Carolina. Because the route distance options are so flexible, this is one of the best tours for bicycling companions of differing riding styles.
This 6-day tour offers routes of 25-50+ miles each day (at your option). Stronger cyclists may bike over 50 miles on a few days of the tour. Less ambitious cyclists can take advantage of short cuts and "leap frog" van shuttles along the route to tailor the route to their needs.
Southern Outer Banks
Tour Operator: Carolina Tailwinds
USA
5 days (Bike: 5 days)
202 mi (~40mi per day)
Leisure
Mostly flat, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
Bike Tour Along North Carolina's Outer Banks & Pamlico Sound
Sparkling sandy beaches, delectable seafood, relaxing ferry rides, and extraordinary biking await you on this special tour. We visit in May, before the crowds build and the weather is perfect for bicycling. Enjoy two nights in Ocracoke Village, "the Pearl" of the Outer banks.
We cycle 25-40 miles each day (at your option) along flat terrain. Strong coastal winds sometimes present a minor challenge, but they are just as likely to propel us along our route! Two ferry rides during the tour allow pleasant opportunities to relax. Along the way, observe coastal wetlands as you bike through the Cedar Island National Wildlife Refuge and charming undeveloped Ocracoke Island.
Southern Shenandoah Tour
Tour Operator: Carolina Tailwinds
USA
5 days (Bike: 5 days)
321 mi (~64mi per day)
Active
Hilly, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
Bike tour of Virginia's Allegheny & Blue Ridge Mountains and the Great Valley Between
A Spectacular 5 Day Cycling Tour of SW Virginia
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 through the rolling valleys, forest roads through the quiet George Washington National Forest, and the Blue Ridge Parkway along that famous ridge top provide some of the most beautiful bicycle routes you could ever hope to ride. Nightly, relax in gracious inns -- one in a beautiful country setting, and two in downtown historic districts.
Colonial Virginia
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
307 mi (~51mi per day)
Leisure
Some hills, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
A Bike Tour of Williamsburg, Jamestown & Yorktown Virginia
A Bicycle Tour of the Founding of America
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, and the incomparable living historic park that is Colonial Williamsburg. Bike routes on gently rolling hills and flat terrain connect these sites and more. Lodge nightly in magnificent inns rich with colonial style and dine in fine restaurants nightly.
Middle Tennessee
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
325 mi (~54mi per day)
Active
Some hills, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
A Six Day Cycling Vacation of Rural Middle Tennessee
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.
The terrain is a combination of gently rolling terrain, hills, and, in a few spots, challenging climbs. As with all of our tours, less ambitious cyclists can take advantage of short cuts and strategic "leap frog" van shuttles along the route to tailor the route to their needs.
Florida First Coast Tour
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
271 mi (~45mi per day)
Leisure
Mostly flat, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
Bike Tour of Florida's Northeast Coast
A Six Day Cycling Vacation of St. Augustine, Amelia Island and A1A
Starting in the resort area of Palm Coast, Florida, this tour covers some amazingly diverse bicycling -- from famous route A1A along the blue waters of the Atlantic to country roads providing scenic views of "Old Florida." Along the way, we explore historic Saint Augustine, pristine Amelia Island, and numerous inviting coastal communities.
Bike Tour of Wisconsin’s Door County
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
312 mi (~52mi per day)
Leisure
Some hills, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
A Beautiful Bike Tour of the Martha’s Vineyard of the Midwest.
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 scenery are inviting small towns and villages—each one charmingly different from the next. Well-kept dairy farms and cherry and apple orchards dot the horizon with their ever-present red barns. No matter where you are, the wealth of rural or water views and fabulous lightly traveled roads create perfect conditions for cyclists of all abilities. Come with us to find out why Door County, WI has earned the nickname, “the Martha’s Vineyard of the Midwest!”
The terrain is a mix of gently rolling hills and flat terrain, making it accessible to all ability levels. Road bikes and hybrid style bikes are both appropriate. This 6 day tour offers routes of 25-50+ miles each day (at your option). Less ambitious cyclists can take advantage of short cuts and "leap frog" van shuttles along the route to tailor the route to their needs.
Bike Tour of the Adirondacks and Vermont
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
318 mi (~53mi per day)
Active
Some hills, On-road
Guided
Supported
Prices from
Guided
Please Ask
Overview
Tour Operator Carolina Tailwinds
A Six Day Cycling Vacation of the Southern Adirondacks and Vermont
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 the prettiest areas of two states.