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.
Bike Tour of Virginia's Blue Ridge Mountains
Tour Operator: Carolina Tailwinds
USA
5 days (Bike: 5 days)
305 mi (~61mi per day)
Moderate/Advanced
Guided
Prices from
Guided
US$ 1795
Overview
Tour Operator Carolina Tailwinds
A Cycling Vacation from Roanoke to Blacksburg to Floyd
Come ride the Blue Ridge Mountains. Southwestern Virginia is home to beautiful sections of the Blue Ridge Parkway, the charming arts community of Floyd, bustling Blacksburg and mile after mile of beautiful road cycling.
This itinerary is great for the cyclist who doesn't care for van shuttles. There is only one short shuttle built into the itinerary. Otherwise, bike inn-to-inn each day!
Maryland's Eastern Shore
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
250 mi (~42mi per day)
Guided
Prices from
Guided
US$ 2275
Overview
Tour Operator Carolina Tailwinds
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 quaint communities greet you along the way.
NY Finger Lakes Tour
Tour Operator: Carolina Tailwinds
USA
6 days (Bike: 6 days)
344 mi (~57mi per day)
Moderate
Guided
Supported
Prices from
Guided
US$ 2495
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)
Moderate
Guided
Supported
Prices from
Guided
US$ 2710
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)
Easy
Guided
Supported
Prices from
Guided
US$ 2425
Overview
Tour Operator Carolina Tailwinds
A Bicycling Vacation of Charleston and Coastal South Carolina
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
7 days (Bike: 6 days)
264 mi (~44mi per day)
Easy
Guided
Supported
Prices from
Guided
US$ 2850
Overview
Tour Operator Carolina Tailwinds
Bike Tour of Ocracoke Island and North Carolina's Outer Banks
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 complete our adventure in the historic islands haunted by Blackbeard’s legend!
Designed for flexibility, our routes offer 15 - 50+ miles each day (at your option). Stronger cyclists may bike over 50 miles on each day of the tour, including up to 75 on one day. Less ambitious cyclists take advantage of short cuts and "leap frog" van shuttles along the route to tailor the route to their needs. Because the route distance options are so flexible, this is one of the best tours for bicycling companions of differing riding styles.
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! Several ferry rides are scattered throughout this tour, allowing pleasant opportunities to relax. Along the way, observe coastal wetlands as you bike through the Cedar Island National Wildlife Refuge and Ocracoke Island.
Southern Shenandoah Tour
Tour Operator: Carolina Tailwinds
USA
5 days (Bike: 5 days)
321 mi (~64mi per day)
Moderate
Guided
Supported
Prices from
Guided
US$ 2095
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)
Easy
Guided
Supported
Prices from
Guided
US$ 2545
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)
Moderate/Advanced
Guided
Supported
Prices from
Guided
US$ 2425
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.
NC Horse Country Tour
Tour Operator: Carolina Tailwinds
USA
5 days (Bike: 5 days)
309 mi (~62mi per day)
Moderate/Advanced
Guided
Supported
Prices from
Guided
US$ 1825
Overview
Tour Operator Carolina Tailwinds
Bike Tour Along the Rolling Heartland of Central North Carolina
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, and the pristine landscape of some of America's most legendary golf courses. An authentic "southern hospitality" experience awaits you in NC's Heartland.
The terrain is moderately hilly to hilly, making it ideal for intermediate and advanced level cyclists. All routes are on paved roads, so road bikes or road oriented hybrids are recommended. Routes will total 40-75 miles each day. Opportunities to extend your miles, or shorten them with a "leapfrog shuttle" exist daily. All of the routes are on country back roads, and the scenery is beautiful, including hardwood forests, longleaf pine forests, peach orchards, cotton fields, equestrian estates, golf courses and small towns.