…‘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.
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Trip Overview
Price
Early bird discount: $2825 per person
Full price: $2925 per person
Bicycle rental : $100
Single room supplement: $625
Upcoming tour dates & status
- 8/3/25 – 8/8/25
- 8/10/25 – 8/15/25
- 8/17/25 – 8/22/25
- 8/24/25 – 8/29/25
Meeting/Departure Point
Nearest Airport
TVC Cherry Capital Airport
Duration
6 days, 5 nights
Tour difficulty
Gently rolling to moderately hilly
Included
- Lodging:
5 nights at boutique inns and town hotels. - Meals:
Dinner on nights 1, 3 & 5; all lunches except 2; 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 from Traverse City:
Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Traverse City airport and surrounding Traverse City inn locations to and from our tour start at Hotel Indigo, Traverse City, MI. Timing formally coordinated 2 weeks prior to the tour date.
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
20–43 miles, sections of flat shoreline terrain along with some rolling hills. Total elevation gain of up to 1200 feet.
After a brief orientation meeting and light lunch, we will start our week of pedaling! Our first day of bicycling takes us along the quiet agrarian back roads of the Old Mission Peninsula with numerous cherry orchards, vineyards and hops farms dotting the landscape. A longtime locals’ favorite ride, we bike north along the shoreline of this skinny spit of land that partially bisects Grand Traverse Bay. We stop briefly at the peninsula’s northernmost point for a visit to the Mission Point Lighthouse dating back to 1870. Our ridge top ride returning to Traverse City provides awesome views of both Grand Traverse Bay and Little Traverse Bay. Stop along the way for a taste of local wine or craft beer, or simply wait until the end of the ride to sample Michigan’s booming craft beer industry at one of the 16 micro-brewery locations within walking distance of our hotel.
Dinner is together as a group tonight within walking distance of our hotel.
Day 2
25–60 miles, flat in spots with rolling hills. total elevation ranges from 365 to 1200+ feet of climbing, distance dependent.
Today is a special day filled with mammoth lakeshore sand dunes and stunning Lake Michigan views! Sleeping Bear Dunes National Park won the title of “Good Morning America’s” Most Beautiful Place in America and is one of the nation’s best-kept secrets. We start our day with an early morning shuttle to maximize our time in this treasure of a National Park. Clamber up the 300 foot “Dunes Climb” in your bare feet. Back on the bike, take on the challenging but rewarding Pierce Stocking Scenic Drive. (shuttle option available.) This route winds through a wooded area of the giant sand dunes and accesses the park’s most spectacular overlook, where you will revel in views of the aquamarine waters of Lake Michigan. Cycle miles of paved off road bike paths that wind through the National Park grounds. Explore historic buildings describing 20th century life in the early lakeshore settlements. We’ll stop for lunch in charming Glen Arbor and have a chance to revel in all things cherry at Cherry Republic, “the largest exclusive retailer of cherry products in the United States.” The afternoon offers the option of another short shuttle before completing our late afternoon journey back to Traverse City on the Leelanau Trail. Running through the last of Leelanau County’s former railroad corridors, the Leelanau Trail features picturesque forests, farms, vineyards, lakes and ponds and is an amazing cycling resource in the area.
The evening is yours to explore the many options awaiting you in Traverse City, MI.
Day 3
28–65 miles, flat in spots, with some rolling hills. Total elevation ranges from 1216 – 3645+ feet.
We bid goodbye this morning to fun Traverse City and begin with a short shuttle. Miles of quiet tree-lined roads lead us to Charlevoix, one of the hidden gems of northwest Michigan’s Lower Peninsula. Situated on a spit of land between Lake Michigan and Round Lake, the downtown is known as “Charlevoix the Beautiful.” With abundant flowers lining the main street and boarding the park overlooking the marina where yachters dock for day trips, Charlevoix really is a beautiful sight worth savoring. Grab a picnic lunch to refuel in the expansive grassy park overlooking the water before tackling the afternoon’s optional miles.
The Little Traverse Wheelway is a 24 mile paved bike trail connecting Charlevoix, Petoskey and Harbor Springs and offering picture postcard views of Lake Michigan. We take advantage of this amazing shoreline resource to roll to our home base for the next 3 nights, Petoskey. Be sure to stop along the way for the many photo ops available!
The afternoon is yours to spend as you choose. Continue on your bike to explore Harbor Springs, pedal along the paved paths to the interesting historic Oden Fish Hatchery Visitor’s Center, or take time off the bike for strolling the streets of Petoskey thick with boutique stores, pubs and restaurants. Our hotel, the Stafford’s Perry, is only steps away from the heart of the historic shopping district.
Dinner will be as a group this evening at one of Petoskey’s many excellent options.
Day 4
8–65 miles, flat in spots, and includes some climbing along the way. elevation gain on the island is variable but can be up to 760 feet. elevation gain on the alternate route is also variable, but can be up to 1662 feet.
Our big day and a day full of choices! After breakfast, we depart for a shuttle to Mackinaw City, the jumping off point for an optional, included excursion to Mackinac Island. Mackinac Island is a step back in time to a car free era with only bikes and horse drawn carriages for transportation. The eight mile perimeter road offers spectacular views, and the town is full of restaurants, museums and sites, so the island will give you plenty to do all day. A late afternoon return shuttle will get you back to Petoskey.
While Mackinac Island is on the bucket list of many visitors to this region, we know several of you have already “been there, done that.” For those folks, we have the alternate itinerary of a supported bike ride that revisits the Little Traverse Wheelway in the spectacular morning light along the shores of Lake Michigan. The scenic views from the Charlevoix Yacht Club provide additional postcard worthy photo ops.
We continue to the shores of the wishbone shaped Lake Charlevoix and the historic Ironton Ferry. The tiny vessel named the Charlevoix holds 4 cars (in addition to cyclists!) and made the “Ripley’s Believe It Or Not” newspaper feature noting that its captain traveled more than 15,000 miles without being more than 1,000 feet from home. The south shores of Lake Charlevoix sparkle in the sunlight and provide an amazing backdrop to today’s low traffic journey. The route is mainly flat leading to the relaxing Boyne City hub at the eastern edge of the lake. Boyne City thrived as a regional logging center in the 19th century and still has preserved some of its “Wild West” charisma. In the early part of the 20th century, Ernest Hemingway summered here in his family’s home on nearby Walloon Lake. Stop in the preserved Boyne City General Store to peruse a wall full of memorabilia dedicated to the celebrated writer
Dinner tonight is “on your own” to explore the many options available in bustling Petoskey and make the most of the flexibility offered to you today.
Day 5
16–60 miles, flat with some rolling hills as always.
Today offers one of our favorite rides in the area! Along the shores of Lake Michigan and through the fabled “Tunnel of Trees” (M-119) northwest of the summer resort town of Harbor Springs. This paved, low traffic road winds its way along the bluffs high above Lake Michigan before connecting back to the paved dedicated Little Traverse Wheelway leading you to Petoskey. Stop at the eccentric and iconic Leg’s Inn for authentic Polish cuisine, served by the same family since the 1920’s. Purchase your own M-119 souvenirs at the remote Good Hart General Store.
Day 6
0–50 miles, flat in spots, and includes some climbing along the way.
Our final day will include a short van shuttle back toward the shores of Little Traverse Bay. We bike another local favorite route down the scenic east shore of Torch Lake before rejoining the ridge top roads leading back into Traverse City. The final few miles will use the Traverse Area Recreational Trail, a rails to trails. Showers and lunch will be provided before heading out.
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
- Transportation back to starting point
- 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
Hotel Indigo
Within an easy walk to downtown attractions and offering a spectacular view of Grand Traverse Bay, this new hotel also boasts spa-inspired showers and numerous modern amenities.
Nights 3, 4 & 5
Stafford’s Perry Hotel
An 1899 landmark in the heart of downtown Petoskey, this 79 room hotel is home to the Noggin Room, one of the best places to grab a pint.
Get Prepared!
Cycling
The terrain is flat in spots, but does include some elevation gain each day. Cyclists will encounter a mix of gently rolling hills, with some short hilly sections, and flat terrain, making it accessible to all ability levels. Road bikes and hybrid style bikes are both appropriate.
This 6 day tour offers routes of 25 – 60+ miles each day (at your option). Mileage each day will range from 35 – 65 miles. As with all Carolina Tailwinds tours, you can take advantage of the support van to “leap frog” ahead on the route and tailor the route and route distance to your needs.
Tour Point of Origin
Hotel Indigo, 263 W Grandview Pkwy, Traverse City, MI (231) 932-0500
Getting to the Tour Start (Traverse City, MI):
Driving: Approximate travel distance to Traverse City–
- Cincinnati, OH: 488 miles
- Detroit, MI: 242 miles
- Grand Rapids, MI: 140 miles
- Mackinaw City, MI: 102 miles
- Chicago, IL: 305 miles
- Toronto, ON: 280 miles
Airports:
Cherry Capital Airport, (TVC) Traverse City, MI is 6 miles from our tour start location. Served through Detroit by Delta and through Chicago by American and United. tvcairport.com
Ground Transit:
Taxi cabs and Ubers are available at the Traverse City airport. Carolina Tailwinds will provide a courtesy shuttle from the TVC airport the morning of Day 1 of the tour. We can also pick up at any Traverse City airport hotel, or your chosen downtown hotel should you opt to stay additional nights at a different location.
On the last day, we will drop guests at TVC if needed.
Parking: We have arranged for long term parking for the duration of your tour. We will end the tour in Traverse City with an opportunity to shower prior to departure.
Arrival/Departure Timing
Arrive at the tour start location no later than 11:30 a.m. on Day 1 (10:30 a.m. if renting a bicycle.) Arrive a day or more early to enjoy Traverse City and all it has to offer on your own.
We will return to Traverse City on Day 6 between 2 and 3 p.m. Your return flight should depart no earlier than 4:00 p.m.
Extend Your Vacation
Be aware: if you are expecting to book additional nights in Traverse City, you need to look into that early. T.C. is a very popular weekend destination during the summer, and every available hotel room is full every weekend. Most hotels require a two night minimum.
There is much to see and do in Traverse City and beyond.
Traverse City: Add a night or 2 to your stay in the area to explore this town with style and substance. While there is no doubt that tourism drives the local economy, Traverse City remains a real community with hardware stores and office shops next to gift shops and galleries. Sip your way through the Traverse City Ale Trail, add an excursion for wine-tasting along the bay, or rent a kayak for a summer paddle on the scenic bay which remains the top draw of Traverse City in the summer.
Interlochen, MI: Located 14 miles south of Traverse City, the Interlochen Center for the Arts operates a year round school for gifted students to explore music, dance, theater, film, literature, and visual arts. Hundreds of concerts, readings, film screenings, dance and theatrical performances, and art exhibitions are open to the public. The offerings are diverse and always impressive.
Cadillac, MI: 1 hour south of Traverse City. A vibrant downtown and Lake Cadillac, along with a couple of affordable hotels make this a nice option when driving to T.C. Check out the KISS monument.
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?
See What Our Customers Say About Us
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.
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.
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.