Take a South Carolina bike tour in the Lowcountry with our captivating 6-day coastal vacation. Embark on a journey that seamlessly blends the region’s rich history, natural splendor, and legendary hospitality for an unforgettable experience. From the quaint streets of Beaufort to architectural gems of Charleston SC, each day promises a new adventure filled with exploration and discovery.
We did the Florida tour with a group of 16. The inns selected by Anne and Greg were a pleasant surprise as were the restaurants. Steve’s patience and guidance while biking was greatly appreciated. We have toured together before but this was the most supported experience we have had. Their bikes were excellent. I highly recommend scheduling with this company.
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Trip Overview
Price
Early bird discount: $2775 per person
Full price: $2875 per person
Bicycle rental : $100
Single room supplement: $620
Upcoming tour dates & status
- 4/20/25 – 4/25/25
- 10/19/25 – 10/24/25
Meeting/Departure Point
Nearest Airport
- Arrive at SAV Savannah/Hilton Head International
- Depart from CHS Charleston International
Duration
6 days, 5 nights
Tour difficulty
Flat, easy terrain
Included
- Lodging:
5 nights at boutique inns in the heart of charming downtowns - Meals:
Dinner on nights 1, 3 & 5; all lunches except 1; all breakfasts; snacks; and hors d’oeuvres most nights. - Full Route Support & Luggage Transfer:
Service of 1 – 2 support vans on route every day. - Complimentary Airport Transportation:
On the front end, Carolina Tailwinds provides a shuttle from the Savannah, GA (SAV) airport, airport hotels, and downtown Savannah hotels to our tour start in Beaufort, SC. Timing formally coordinated 2 weeks prior to tour date.At the end of the tour, Carolina Tailwinds provides a shuttle to the Charleston International Airport (CHS) and surrounding hotels.
Please note: there is no complimentary shuttle from CHS at the beginning, or to SAV at the end, although you are welcome to make your own arrangements.
Group Size
Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours
About your guide
Expert guides ready to show you the hidden wonders of each and every destination
What You’ll See & Do
Day 1
10–20 miles, flat terrain
We meet at midday at the lovely Rhett House Inn in the heart of the historic district. After orientation and bicycle fittings, we’ll pedal Beaufort’s lovely neighborhoods where quiet streets between stately antebellum homes and Live Oaks draped with Spanish moss give us our first taste of South Carolina’s charms. Pedal the Spanish Moss Trail, Beaufort’s outstanding new rail trail. You’ll learn about Beaufort’s and South Carolina’s colorful history before biking back to the inn. We relax before dinner as a group this evening, where we’ll experience our first taste of the savory Lowcountry cuisine for which the area has become famous.
Day 2
32–49 miles, flat terrain
After a delicious hot breakfast at the inn, we bike from the inn toward some of the best biking along the South Carolina coast. Early in the ride, we pass by the Penn Center on St. Helena Island, the school established in 1862 to educate freed slaves. Just down the road, stop to see the ruins of a “Chapel of Ease,” a small chapel built during the plantation era so that wealthy plantation owners could attend church without traveling to the mainland.
We picnic at Hunting Island State Park, one of the most beautiful spots in South Carolina. Biking into the park, you will enter a jungle-like setting as you follow miles of one way roads through a maritime canopy.After lunch, climb the historic Hunting Island Lighthouse for a fantastic view of the SC coast before walking the pristine beach with the Atlantic surf crashing on this barrier island.. Return by bike or by van to Beaufort and savor the soft sea breezes along the waterfront park. Dinner is on your own this evening, with numerous good options within walking distance.
Day 3
18–45 miles, flat terrain
After breakfast, we’ll shuttle north, commencing our bike ride of the tour on remote country back roads near old plantations and cypress swamps. Most of the ride is on exceptionally quiet roads lined with live oaks. We pedal near sites that have been the setting or inspiration of award winning movies such as Forest Gump, Prince of Tides, The Big Chill and countless others.
We’ll then shuttle the rest of the way to downtown Charleston, one of the most charming waterfront towns you’ll ever see. Home base for the next three nights will be the Ansonborough Inn, a beautifully-appointed, all-suite inn centrally located near the Market and Aquarium Wharf in the midst of the historic downtown. Dinner is as a group this evening at one of Charleston’s famous restaurants.
Day 4
0–41 miles, flat terrain (except for one noteworthy bridge)
Today is a flexible day for you to explore Charleston in the way you see fit. Included in your tour price is a narrated one hour carriage tour of downtown Charleston. This is absolutely the best way to soak up a combination of history, architecture and the overall beauty of the “Holy City.” Afterward, join us on a ride that features the thrilling bike path over the Arthur Ravenel Bridge. Completed in 2005, this beautiful structure over the Cooper River dominates the Charleston skyline. From there, explore downtown Charleston on bike or foot on a self-guided tour. Visit the Citadel, Magnolia Cemetery and the College of Charleston at your own pace. Riders looking for more miles can explore Sullivan’s Island, home to the oldest beach resort in the area. At its point is Fort Moultrie where you can learn about three centuries of coastal military history. The Fort defended Charleston’s harbor from the Revolutionary War through WWII. Continue the ride onto Isle of Palms, the next island to the north, connected by bridge across the always scenic Breach Inlet.
Day 5
25–40 miles, flat terrain
Today finds us on one of the loveliest sea islands in South Carolina. We pedal our way through the shady island back roads under arching live oaks full of Spanish moss. We visit the Angel Oak, a live oak believed by many to be over 1500 years old. Our side routes today offer brief glimpses of the salt marshes which define the coastal Lowcountry landscape. We will have a picnic lunch today at America’s only tea farm, and afterwards tour the factory and tea garden grounds.
Day 6
16–30 miles, flat terrain
Our last day includes a meandering route near the rural community of Ravenel. Numerous water views grace the route, as well as hobby farms with exotic animals. After the ride we will finish the commute back to Beaufort for showers, lunch and departure. A shuttle to Savannah and the Savannah airport will be available to those who desire one.
What’s Included in Your Tour Price?
Tour prices are per person rates and include all of the following:
- Lodging costs (double occupancy rooms), including all taxes and fees
- All breakfasts and most lunches
- All dinners described in the tour itinerary (alcoholic beverages in restaurants are generally not included)
- Morning and afternoon snacks
- Route planning and detailed laminated cue cards daily
- Guide support along the route
- Van support along the route
- Luggage transfer
- Fees for all ferries, tolls for all highways and any park entrance or guided tour fees where noted
- Costs for any special activities such as canoeing, kayaking, sailing or rafting where noted
- Carolina Tailwinds t-shirt or day bag, water bottles, complimentary digital photo files from your tour
- Gratuities for restaurants at included meals and gratuities for housekeepers at included lodging
Please note:
All lodging costs are based on double occupancy. The single room surcharge rates apply to single room occupants.
Single travelers who desire a roommate match will be paired with other tour guests of the same gender in a room with two beds, if available. If a match can’t be found for a single traveler, a single occupancy surcharge will be assessed. To find out if a roommate match is available, call us. We will be happy to put you on a waitlist for a match if one is not already available.
Single travelers may request a private room, subject to availability, and to the single room surcharge rate payable in full at the time of the reservation.
Transportation to the tour starting point, including airfare and any airport transfers, is not included in the tour price. We can assist you with making any airport transportation arrangements or advise you on the nearest and most convenient airport.
Alcoholic beverages at restaurants are not generally included . A separate beverage tab may be run for anyone who would like a drink with dinner. Settling this tab will be the responsibility of the individual participants.
Bicycle rental is available as an option (prices above). We have road touring bikes and hybrid bikes for your use and invite you to forego the hassle of transporting your bike to and from the starting point. Click here for more information on the equipment available for your use.
Want to know more about our policies, terms and conditions? Click here to review our deposit requirements, cancellation policy and more.
We will be happy to address any additional concerns or questions you may have.
Simply email us at our Contact Us page, or call us at 1-888-251-3206 (local number is 336.794.1054). Ready to make your reservation? Click here to reserve a spot online, or call us at 1-888-251-3206 (local number is 336.794.1054).
Travel Insurance: We strongly encourage you to consider travel insurance. You may research and compare competing travel insurance policies at websites such as www.squaremouth.com.
Where You’ll Be Staying
Nights 1 & 2
Rhett House Inn is nestled among Beaufort’s Live Oaks draped with Spanish Moss and Resurrection Fern. The inn includes a nearly 200-year-old “in-town plantation house,” and two other graceful buildings. Gracious southern hospitality is matched with modern room amenities. Each room is uniquely and tastefully decorated and includes a hot made-to-order breakfast.
Nights 3, 4 & 5
Ansonborough Inn, Charleston, SC. Freshly remodeled and reimagined in 2024, this stylish hotel features fun spaces, elevated touches, and some of the largest guest rooms in Charleston — each with a distinct layout and 16- to 20-foot ceilings. Unwind at the Rooftop Garden surrounded by the countless steeples of Charleston.
Get Prepared!
Cycling
The terrain is flat, making it accessible to all ability levels. Strong coastal winds sometimes present a minor challenge, but they are just as likely to propel us along our route! Along the way, observe coastal wetlands and rural farmland as we bike the scenic back roads of South Carolina. Because the route distance options are so flexible, this is one of the best tours for bicycling companions of differing riding styles.
This 6 day tour offers routes of 25 – 50+ miles each day (at your option). Stronger cyclists may bike over 50 miles on a few days of the tour. Less ambitious cyclists can take advantage of short cuts and “leap frog” van shuttles along the route to tailor the route to their needs.
Tour Point of Origin
Rhett House Inn, 1009 Craven St, Beaufort, SC 29902 843-524-9030
Getting to the Tour Start (Beaufort, SC):
Driving: Approximate travel distance to Beaufort–
- Atlanta, GA: 287 miles
- Savannah, GA: 45 miles
- Charlotte, NC: 232 miles
- Jacksonville, FL: 178 miles
- Washington DC: 559 miles
Airports:
We recommend that you fly to Savannah / Hilton Head International (SAV) and home from Charleston International (CHS). SAV is approximately an hour away from downtown Beaufort. It is served by American, Allegiant, Delta, Frontier, JetBlue, Southwest and United. CHS is approximately 20 minutes from downtown Charleston and is served by over a dozen airlines.
Ground Transit:
Taxi cabs are available at the Savannah airport. The approximate rate for one person to Beaufort is $80. Each additional person is $10.
A complimentary Carolina Tailwinds shuttle will be available to and from the Savannah airport at a designated time before and after the tour.
Parking: We have arranged for long term parking in Beaufort and in Charleston. You will be able to move your car from our Beaufort lodging to our Charleston lodging on Tuesday.
Arrival/Departure Timing
Arrival time of the first day of the tour is 12:00 noon if renting equipment from us, or 1:00 p.m. if bringing your own bike. Guests will want to meet us at these times dressed in bike clothes, or ready to change into them.
We plan to wrap up around 3:00 p.m. in Beaufort, SC. Your return flight should be no earlier than 7:00 p.m. that evening.
Extend Your Vacation
Before or after our activity packed tour, you may want to tack on a few days. There is a lot to do in and around nearby Savannah if you have time. Carolina Tailwinds will provide a courtesy shuttle from downtown Savannah on Day 1 and/or back on Day 6 if requested.
Of course, you may want to continue your visit to the coast by driving down to the pristine beaches of Kiawah Island, SC or Hilton Head Island, SC.
Rental Bikes for Your Tour
Our Selection
Women’s Road Bike ⇒
⇐ Men’s Road Bike
Hybrid Bike Small ⇒
⇐ Hybrid Bike Large
Step Through Bike ⇒
Why Choose This Tour?
Explore the historic district of Beaufort with its antebellum homes and Spanish moss-draped Live Oaks
Experience the scenic beauty of Hunting Island State Park, where sandy beaches and a historic lighthouse await
Discover the remote country back roads near old plantations and cypress swamps, immortalized in award-winning movies
Immerse yourself in the charm of downtown Charleston, highlighted by a narrated carriage tour and a thrilling bike ride over the Arthur Ravenel Bridge
Pedal through the scenic sea islands of South Carolina, visiting the ancient Angel Oak and America’s only tea farm for a unique cultural experience
See What Our Customers Say About Us
Tailwinds offers routes that can vary from easy to challenging, but that are always scenic and engaging. The support on the road is absolutely best in class, the lodgings are always interesting, and the food is terrific. Best of all, the owners and guides personify “customer service.” Taking a Tailwinds tour is always the highlight of my cycling year. All of this at prices which are reasonable.
We just got back from a fantastic vacation with Carolina Tailwinds. They were super accommodating and fun. The trip had good variety including cycling, two boat rides, beach walk, kayaking, amazing food and happy hour every day. Every expectation was exceeded as they booked a private tour for my husband’s birthday bash. Equipment was fantastic and the guides were personal me and knowledgeable. Booking was easy and every detail was take. Care of. Thank you to the whole team.
We are two retired friends who left our non-cycling husbands at home to have a biking adventure. We throughly enjoyed our Florida tour…Anne and Greg attending to every detail…Although it seemed we were on our own, our guides were at our backs to provide snacks, sun screen, and any assistance needed…The bikers we rented from CT were fitted to us and were maintained in perfect condition…FIRST RATE! We’re ready to book another CT trip!
We have completed 4 trips with Anne and Greg and have another on reservation. Their attention to detail is evident throughout the tour but especially in the excellent route selection. Good riding is of course why most people go on a bike tour and we have never been disappointed with the miles they carefully select. Good food, nice accommodations, interesting off bike activities and leisurely happy hours all adds up to a relaxing vacation.
This company is awesome! I’ve been on several week long tours and this is by far the best company. My husband and I just completed our second tour with CT and every aspect was first class. The guides are attentive no matter what your skill level. We’re planning a third trip next year.!
…Having been on several other bike companies’ tours I have a good perspective to highly recommend Carolina Tailwinds…They were perfectly organized, personally knowledgeable of the routes, and prepared for everything we wanted or needed for a great week…All through the week CT added fine touches to our trip which you’ll just have to experience on your own CT tour. You’ll have an awesome week.
Excellent value. Routes, accommodations, food, activities, support, and equipment were all top notch. Superb attention to details big and small. I have toured with nearly a dozen companies. They were all good, but Carolina Tailwinds has been my favorite. You can spend more, but you won’t get more than you get from Anne and Greg.
The attention to detail and the readiness to accomodate requests from the riders separate Carolina Tailwinds from any other tour group that I have ridden with. One other feature that has to be mentioned is the standard of the accomodations and the food. They are both of the highest standard. The Carolina Tailwind tours are fun!
…The scenery was abolutely spectacular! Traffic was light and road conditions excellent. The routes were well-planned with detailed cue sheets that were easy to follow. The support we received from the CT team was first rate before, during and after each day’s ride. Accomodations were very good if not top of the line. The tour operators, Anne and Greg, are well-organized, friendly, and good companions on a ride. We will be repeat customers this Summer.
Carolina Tailwinds, hands down, is the best bicycle touring company anywhere. Their attention to detail and willingness to accommodate personal preferences are unsurpassed. Their routes are well-planned and the support and ability to deal with different riding levels…My wife and I have done nine tours with Carolina Tailwinds…We are veteran cyclists; if their tours were not really good, we would have never returned…we are going on our tenth this year.
We just signed up for our third tour with this excellent bike tour company. We fly from California just to go with Carolina Tailwinds. Their attention to every small detail is amazing. I think their personal attention as owners of the company is what makes the difference…really do care that each of their customers has the best possible biking vacation.
…The routes afforded beautiful scenery, and were well-supported…We especially liked the personal touch that Anne and Greg provided. They picked us up at our hotel; they kept a watchful eye on rider groups with a broad range of skills; and they hosted informal drinks and hors d’oeuvres each night before dinner…great exercise during the day and relaxing evenings with interesting people, comfortable lodging, and excellent meals.
Aside from knowing some of the most unique biking, lodging, and dining spots in the Mid-Atlantic area, Anne and Greg obviously love what they are doing…This husband and wife team is really tops when it comes to personal, friendly service and they excel in accommodating the needs of riders of all abilities…Our only complaint is that we never seem to lose any weight on their tours, but as they always remind us – “It’s a vacation, you’re not supposed to lose weight!” Looking forward to our fourth trip in four years with Carolina Tailwinds!
Trips are well planned and very well supported. The lodging chosen by the company suits the trips, are comfortable, and often unique. But the most notable item is the personal attention a rider receives throughout the trip. I’ve completed three trips with Carolina Tailwinds and have signed up for a fourth.
…‘Company’ is misleading: this is a personal experience…Count on excellent routing, craft-quality laminated and color-coded cue sheets, a daily pre-ride briefing, convenient and dependable sag support, and smaller, friendly groups. The clinchers for me, though, were the gourmet meals and the accommodations at small inns…I’ve been on 3 different trips with them now, and all cycling agendas have been represented and handled on each trip.
We love this company. We have toured with them three, going on four times and their attention to every detail and their organization skills keep us coming back for more. we have toured with three other companies, vbt, bike vermont, and pedal and sea adventures, and they surpass all of them. Food especially is excellent.
Carolina Tailwinds gives every attention to detail towards their customers. The routes they map out are clear and safe. The accommodations that Carolina Tailwinds select are 5 star all the way, from the lodging to the restaurants. The guides are friendly and accommodating to the cycling level of their guests. The size of the tour group are intentionally small to give the customer that undivided attention they deserve on their vacation.
We had used several bike tour companies and thought that they all did a good job. However, Carolina Tailwinds’ tours are operated by the owners of the company. Thus, their level of service exceeds that of other companies. We have now completed 5 tours with them and have another scheduled. Greg and Anne, the owners, are now like members of our family.
We are in our mid-seventies & have just re-discovered the joys of biking the past 3 years, biking over 2500 miles each of the last 2 seasons mostly hear in upstate NY. We’ve started the past 2 seasons with a Carolina Tailwinds tour & plan to do the same again this season. Anne & Greg just do a terrific job guaranteeing a wonderful vacation for us.
