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

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News from the Road

August 5th, 2023

Carolina Tailwinds Voted #1 Bike Tour...Again!

For the second year in a row, Carolina Tailwinds has placed 1st in the USA Today 10 Best Readers' Choice competition. Thank you to all of you who voted for us. All of us at CT are again humbled, and we will do all in our power to live up to this ranking!

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!