Carolina Tailwinds l Northern Outer Banks Bicycle Tour Bicycle Vacations in the Eastern U.S.A. 

 Experience More...

Welcome l Our Tours l What to Expect l Pricing/Details l FAQ's l Contact Us

What to Expect on a Carolina Tailwinds Tour 

You'll eat well on our bike tours Take a early morning beach walk on our Ocracoke Tour You won't bike far without seeing a lighthouse on the NC coast!


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.  You can also visit our Frequently Asked Questions (FAQ's) page for more information. 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!

Lodging  ·  Meals  ·  Culture  ·  Free Time  ·  Group Size & Profile  ·  Trip Length  ·  Climate  ·  Cycling Miles  ·  The Tailwinds Van  ·  Equipment  ·  Luggage Transfer  ·  Route Planning

"I have described this tour to friends as a cruise with exercise.  Once you arrive, nothing to worry about-- no driving, great food, interesting places... It was great!"  -- Peggy, Brighton, MI



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.

"I thought both of the B&B's were very nice--comfortable, clean, cozy, quaint, etc.  They were very helpful and responsive." -- Glenna, Alexandria, VA

Back to top


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.

"I'm still not sure how I could bike so much and gain weight!  The food was awesome! -- Karen, Chicago

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.  

 Here are links to a few of our regular favorites:

Beaufort Grocery Company, Beaufort, NC: click here
High Cotton, Charleston, SC:  click here
Reluctant Panther, Manchester, VT:  click here
The Whistling Swan, Fish Creek, WI: 
click here
La Pentola, St. Augustine, FL: 
click here

"The chef dazzled us!"  -- Carol, Wilmington, NC 

Back to top


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.     


Back to top

Free Time

Our tours are designed to keep you occupied, but you may choose to diverge from the day’s group activity and venture out on your own.  Each tour features a walkable village location with shops, restaurants, parks, and a myriad of activities at your fingertips.  So should you decide to stay in town instead of venturing out on your bike for a day, there is always something new to explore!  

Back to top

Group Size and Tour Participants

Carolina Tailwinds avoids the “cattle herd” atmosphere of larger tour operators.  Our limited group size (maximum of 18 guests,) and maximum guest to guide ratio of 7:1, allow you to receive our personal attention and creates the opportunity  for you to get to know our other tour guests well.

"This was our fourth biking vacation and our first with Carolina Tailwinds.  The attention to detail and personal service were evident throughout the tour.  I have told several friends about you and hope to tour with you again." -- Dorothy, Raleigh, NC

Sharing your vacation with others who have common interests and with those who contribute their unique perspectives ensures a lively and enjoyable vacation.  The broad appeal of Carolina Tailwinds’  tours draws diverse individuals from a wide range of professions and ages (spanning from age 24 and up).

"I ... felt very comfortable on every level -- socially and athletically."  -- Katharine, Charlottesville, VA

Back to top


Biking and sightseeing can be enjoyed year-round in the eastern U.S.  Early spring and fall are the perfect times to enjoy the southeastern coastal wetlands without slogging through the dreaded southern humidity.  And when those areas heat up in the summer, we take you west to the mild temperatures of the foothills and mountains, central New York, and Wisconsin.  You will receive with your reservation confirmation an average weather chart for your tour as well as a list of recommended items to bring for your chosen tour.  Specific climate data links are available on our Links page.

Back to top

Cycling Routes

Every morning on our tours, we offer you different route options of varying lengths and difficulty.  This allows you the flexibility to choose how much or little time and energy you want to spend on your bike each day.  The route options include daily mileage of as little as 15 miles and as much as 60+ miles.  The choice is yours.  Whichever option you choose, the Carolina Tailwinds Van will be there to help when needed.

The general route difficulty also varies by tour.  Our coastal  and rail trail tours are the easiest.  They are suited for novice or advanced cyclists.  If you are thinking of taking either our Chesapeake Bay Tour, or our Outer Banks Tours, you will find the flat roads to be a blessing, though headwinds can sometimes cause an invisible challenge.  Adirondacks and Vermont, Virginia Blue Ridge, Southern Shenandoah and Northern Shenandoah are most difficult, and are best enjoyed by intermediate and advanced cyclists.  On our Middle Tennessee, NY Finger Lakes, and NC Horse Country Tours, you will be pedaling up some rolling hills, so it is best for intermediate and above as well.  

In general, most of our chosen daily routes allow for 3 to 6 hours "in the saddle".  As with any vacation you would plan for yourself, you have the freedom to pedal  on your own schedule.  You can dawdle at magnificent views, take your time meandering through pastoral back roads, or bike as if you are a competitor on the Tour de France.  The pace and distance traveled is controlled by you.

If you are still unsure which tour is right for you, call us at 1-888-251-3206 and we will be happy to assist you!

The Tailwinds Van 

"The van support was great - always there when we needed it!"  --  Stacey, Unionville, CT

On a Carolina Tailwinds tour, you will be secure in the knowledge that our van will be along to provide refreshments and support whenever you need them.  We have several established check points along each of our planned routes.  These check points enable Carolina Tailwinds to maintain close contact with you at whatever pace and schedule you set.  Our van allows experienced and inexperienced cyclists the chance to enjoy the same terrain on their own terms and pace.

Back to top


"Bikes and setup expertise were excellent."  --  John, Roswell, GA

Though you are welcome to bring your own bike, Carolina Tailwinds’ low bicycle rental charges allow you to forego the hassle of transporting equipment to the tour rendezvous.  We maintain a fleet of high quality bikes.  Hybrids are late model  Fuji Absolute One's.  Our road bikes are carbon fiber endurance frame bikes by Lapierre and Raleigh which have compact cranks and 10 speed rear cassettes.  Your rental bike, regardless of style, will have an adjustable rise handlebar stem and quick release seat post clamp for an easy fit.  A bag is on your bike to tote the day’s necessities.  We recommend our lightweight road bikes for the mountainous and hilly tours, and either road or hybrid for our coastal tours.  We also provide you with a new water bottle with our Carolina Tailwinds’ logo that is yours to keep.  Helmets are absolutely required on all rides.  We encourage you to bring your own  or we will be happy to provide one.  You may also bring your own saddle and/or pedals for us to install on a rental bike for you.

Back to top

Tour Photos

Since we know where many great photo opportunities are on your tour we take pictures as we go.  Each guest is provided online access to all of our shots, and prints and other products can be ordered easily and inexpensively.

Back to top

Luggage Transfer 

We take care of shuttling your luggage and any items bought  along the way to your next destination.  This leaves you free to enjoy the surrounding area without any added weight on your bike.   

Back to top

Route Planning

"The routes were perfect for a nice relaxing vacation, with just the right amount of challenging hills."  --  Sally, Durham, NC

We begin each day with a brief overview of what to expect on the day’s ride, including timing and terrain, and what additional special activities we have planned.  We supply you with detailed cue sheets of the day’s route, including mileage markers and optional side trips, and prior to sending you on your way.  One of our guides is always cycling with you to provide any answers about what lies ahead.

Back to top


Welcome   |   What to Expect   |   The Tours  |   Pricing & Details   |   Contact Us
Who We Are   |   FAQs   |  Online Reservation Form  |  Recommended Links  | Employment

©  Carolina Tailwinds, Inc.  "Carolina Tailwinds" and the Carolina Tailwinds Logo are Service Marks of Carolina Tailwinds, Inc.

Carolina Tailwinds   P.O. Box 24716   Winston-Salem, NC 27114-4716   888.251.3206 or 336.794.1054