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.

Bike tour: Bike Tour of Virginia's Blue Ridge Mountains

Bike Tour of Virginia's Blue Ridge Mountains

  USA

 5 days (Bike: 5 days)

  305 mi  (~61mi per day)

 Moderate/Advanced

Guided

Prices from

Guided

US$ 1795

Bike tour: Maryland's Eastern Shore

Maryland's Eastern Shore

  USA

 6 days (Bike: 6 days)

  250 mi  (~42mi per day)

Guided

Prices from

Guided

US$ 2275

Bike tour: NY Finger Lakes Tour

NY Finger Lakes Tour

  USA

 6 days (Bike: 6 days)

  344 mi  (~57mi per day)

 Moderate

Guided

Supported

Prices from

Guided

US$ 2495

Bike tour: Georgia's Historic Heartland

Georgia's Historic Heartland

  USA

 6 days (Bike: 6 days)

  289 mi  (~48mi per day)

 Moderate

Guided

Supported

Prices from

Guided

US$ 2710

Bike tour: South Carolina Low Country

South Carolina Low Country

  USA

 6 days (Bike: 6 days)

  225 mi  (~38mi per day)

 Easy

Guided

Supported

Prices from

Guided

US$ 2425

Bike tour: Southern Outer Banks

Southern Outer Banks

  USA

 7 days (Bike: 6 days)

  264 mi  (~44mi per day)

 Easy

Guided

Supported

Prices from

Guided

US$ 2850

Bike tour: Southern Shenandoah Tour

Southern Shenandoah Tour

  USA

 5 days (Bike: 5 days)

  321 mi  (~64mi per day)

 Moderate

Guided

Supported

Prices from

Guided

US$ 2095

Bike tour: Colonial Virginia

Colonial Virginia

  USA

 6 days (Bike: 6 days)

  307 mi  (~51mi per day)

 Easy

Guided

Supported

Prices from

Guided

US$ 2545

Bike tour: Middle Tennessee

Middle Tennessee

  USA

 6 days (Bike: 6 days)

  325 mi  (~54mi per day)

 Moderate/Advanced

Guided

Supported

Prices from

Guided

US$ 2425

Bike tour: NC Horse Country Tour

NC Horse Country Tour

  USA

 5 days (Bike: 5 days)

  309 mi  (~62mi per day)

 Moderate/Advanced

Guided

Supported

Prices from

Guided

US$ 1825

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While great care has been taken to show full and correct tour details, unfortunately transcription errors do occur and, although we continually seek to eliminate these, we apologise for any mistakes. Plans or bookings should not be made exclusively based on information shown on this website but must be confirmed with the tour operator.