Carolina Tailwinds Bicycle Vacations

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Carolina Tailwinds Bicycle Vacations Bicycling Vacations in the Eastern USA
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01/03/2024

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A Day in the (Island) Life Bicycle Adventures in Eastern USA Imagine YOUR Perfect Day on the NC Outer Banks NC's barrier islands, with the Atlantic surf crashing on the east and the Pamlico Sound wetl

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01/02/2024

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Plan your bicycle adventure in 2024! Bicycle Adventures in Eastern USA Unique sights from a few of our "happy cycling places"... Hello Friends! We think it is safe to assume that we share a common ple

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12/04/2022

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Bicycle Adventures in Eastern USA Greetings Team CT! It's Poll Stuffin' time again! The USA Today 10 Best folks are updating their poll of best bike tours, and Carolina Tailwinds is again nominated. W

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20/01/2022

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Greetings from North Carolina, which is an icy wintry mess at present. Great sledding, not optimal cycling. Time to dream about (and plan for) SPRING. Looking ahead: a few of our springtime faves... S

04/01/2022

Happy National Trivia day! In what year and where was the first Carolina Tailwinds Tour Bike tour?

We’re hiring for our 2022 season! Is there someone in your family or circle of friends who you think would make a great ...
28/12/2021

We’re hiring for our 2022 season! Is there someone in your family or circle of friends who you think would make a great asset to Carolina Tailwinds? Send them our way, we’d love to meet them. If you’ve traveled with us before, you know how lucky we are to have such amazing, dynamic and inspiring people as a part of our team. We’re looking to expand the and are hiring Tour Guides – those folks on the front lines who are great communicators, hard-working, have a love of traveling and people and enjoy an active lifestyle.

https://www.carolinatailwinds.com/careers

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22/12/2021

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Asparagus Wheel Tart Bicycle Adventures in Eastern USA 2021 was a year of getting back to the activities we enjoy, and a year of enjoying them with people we cherish. Thank you to all of our friends:

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18/12/2021

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Calling all future guides! We're hiring for our 2022 season and can't wait to meet you! Find out more about what it take...
16/12/2021

Calling all future guides! We're hiring for our 2022 season and can't wait to meet you!
Find out more about what it takes to show people the vacation of a lifetime.

https://www.carolinatailwinds.com/careers

If you think Florida is all amusement parks and strip malls, you haven’t been there with us.  Our tour of Florida’s Firs...
07/03/2021

If you think Florida is all amusement parks and strip malls, you haven’t been there with us. Our tour of Florida’s First Coast provides miles and miles of coastal beauty and many glimpses of the “Real Florida.” We’ll be back for more fun in the sun in late October and early November. Ride coastal route A1A, have lunch in a marina tiki hut, spot dolphins on a chartered boat cruise, and walk the beach at sunrise. As with all of our trips, the lodging is luxurious, and the dining is superb. Come join us!
https://www.carolinatailwinds.com/tour/florida-first-coast

Wishing love and happiness to all.  This is a little public art along one of our favorite bicycle trails.  Anyone know w...
13/02/2021

Wishing love and happiness to all. This is a little public art along one of our favorite bicycle trails. Anyone know which trail it is?

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Carolina Tailwinds Bicycle Vacations

Carolina Tailwinds was started by Greg and Anne Fleming 21 years ago out of their passion for touring an area by bicycle and wanted to share that passion with others. We have been fortunate to expand from our home stomping grounds of North Carolina over the years to specialize in highlighting the best East Coast and Midwest USA bicycling destinations.