Fully supported inn-to-inn bicycle tours

Best USA Cycling Vacation Tour Company — Carolina Tailwinds Bike Tours

We provide carefully planned multi-day bicycle tour packages that include fine dining, memorable lodging, beautiful cycling routes and full support, all in a small group environment. We offer 16 destinations in 10 states throughout the Eastern U.S. Come ride with Tailwinds!

The Carolina Tailwinds Experience

Sign up for Tour Announcements & Deals

Sign Up

Start Your Bike Tour

See how Carolina Tailwinds gives you an amazing trip.

Browse Tours

News from the Road

June 24th, 2022

Carolina Tailwinds Voted #1 Cycling Tour

Carolina Tailwinds is proud to announce that we were voted #1 Cycling Tour in USA TODAY's 10BEST 2022 Readers’ Choice Awards.

This come on the heels of top 4 finishes each of the previous 2 years. As before, Carolina Tailwinds was one of twenty companies nominated across the country, chosen by the panel of experts. The top 10 bicycle tour companies were then chosen by popular vote and awarded the 10Best Readers Choice Award.

April 7th, 2020

Grandmothers, Gravy and Old Bikes

Holiday Memories and Bikes on a Holiday Week

Do you ever feel like today’s conversation is dominated by code phrases? Who knew, at the beginning of 2020, that terms like ‘Social Distancing’ and ‘Flattening the Curve’ would be commonplace in our daily lexicon? In 2019, I would have thought that meant biking a safe distance away from everyone else to avoid a crash, or somehow making biking up that huge hill not as hard to tackle!

Click Title to continue reading.

February 27th, 2018

FAQ's about Bike Tours

Do I have to be a strong rider?

No! Since 2000, we have designed fully-supported cycling vacations that cater to all types of riders. Whether you average 8 miles per hour or 20, we have a route for you! Strategically placed van stops can leap frog riders over hills or provide a comforting ride if you're out of steam. From our flat terrain tours to our hilly and mountainous tours, we have the terrain for a perfect vacation for YOU.