The Experience

What to expect with Carolina Tailwinds

Carolina Tailwinds tours are carefully planned well in advance. We handle the details so that you can relax and enjoy cycling, scenery and other activities. Listed below some of the details that you may wonder about. Or you can simply e-mail us your question at our Contact Us page and we will be happy to answer your concerns. We look forward to serving you on your vacation!


Each night, you will stay in Carolina Tailwinds favorite country inns or boutique hotels. Our hosts each night greet us with graciousness and hospitality. All of the rooms we arrange for our guests have private bathrooms. Most include tasteful furnishings which welcome instead of overwhelm you. Our choices in inns reflect our personal preference for well-managed inns with personality. You can peruse the individual tour pages for detailed descriptions of Carolina Tailwinds’ lodging selections or for links to the inns’ own web pages.


Great food is always best enjoyed after an active day. We have selected the finest restaurants along all of our routes. From the lemon soufflé pancakes for breakfast to the shrimp and mushrooms over cappellini with saffron sherry cream for dinner, we can promise you will always find something delectable to eat. All of Carolina Tailwinds’ chosen favorites provide opportunities for you to try fantastic regional cuisine. Unlike many tour operators, we do not limit you to one or two options. You will be able to order from a menu each night that includes a range of options. Of course, if you have any special dietary needs, simply make them known in advance and we will be sure they are satisfied.

Gourmet breakfasts, most lunches and most dinners are included in your trip price. Lunches are provided by the best local caterers. We also supply the much needed morning and afternoon snacks and water bottle refills along the day’s route. We usually plan for one or two evening meals to be on your own in towns with multiple fine restaurants within easy walking distance of your inn. Thus, you can spend your free evening with your partner or friends, or opt to dine in the company of your newfound acquaintances met on our tour.


We have a fleet of well maintained road and hybrid style bicycles ready to roll.  You can rent one or bring your own.  Check out our rental fleet by clicking HERE.

Group Dynamics

Bicycle tours generally attact a fun, outdoor-loving clientele.  Most are successful professionals in a wide range of professions, sharing a common interest.  Our groups usually transform themselves from a collection of strangers to amiable companions within one day and are frequently a cadre of new best friends in five days.  If there is a better venue for meeting interesting and successful people who share a love of cycling and travel, we don't know what it is!


While all of Carolina Tailwinds tours focus on providing an enjoyable and active biking vacation, we also structure each trip to include an insider’s glimpse into the region. On our coastal tours, you may visit historical sites, lighthouses, and wildlife refuges. Our wine tours try to coincide with the local vineyard harvest schedules, allowing you a detailed glimpse into the art of wine making. Our mountain tours may lead you to  refreshing waterfalls, Christmas tree farms, or mountain musical venues. The Colonial Virginia Tour and South Carolina Lowcountry Tour are the trips with the most "off the bike" items of interest. We want to supply you with lifetime memories of a well-balanced, fun and active tour, the kind of tour you would plan for yourself.

News from the Road

June 25th, 2024

Three-peat! #1 Cycling Tour again in 2024

Thank you once again loyal friends and patrons who vote us Number 1 US Bike Tour Company in the 2024 USA Today 10Best Readers Choice Award!  We appreciate your votes and your faith in Carolina Tailwinds.

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.