Nestled between the blue waters of Green Bay and Lake Michigan, Wisconsin’s Door County stretches out like a picturesque peninsula, boasting 75 miles of dramatic limestone cliff faces, pristine sandy beaches, and breathtaking water views. Peppered throughout this stunning natural landscape are a collection of inviting small towns and villages, each with its own unique charm and character. From well-kept dairy farms to cherry and apple orchards, the horizon is adorned with the iconic red barns that epitomize the rustic beauty of the Midwest.
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.
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Trip Overview
Price
Early bird discount: $2825 per person
Full price: $2925 per person
Bicycle rental : $100
Single room supplement: $650
Upcoming tour dates & status
- 6/8/25 – 6/13/25
- 6/15/25 – 6/20/25
- 6/22/25 – 6/27/25
- 8/31/25 – 9/5/25
Meeting/Departure Point
Lodge Kohler, Green Bay, WI
Nearest Airport
GRB Green Bay–Austin Straubel International Airport
Duration
6 days, 5 nights
Tour difficulty
Hilly terrain, with a few challenging climbs
Included
- Lodging:
5 nights at boutique inns and lakefront resorts. - Meals:
Dinner on nights 1, 3, 4 & 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.
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
30–45 miles, gently rolling hills and flat terrain
The trip begins in Green Bay, at a luxury hotel next to Lambeau Field. Arrive early to take the tour of Lambeau and the Green Bay Packers Museum and Hall of Fame.
Our group will meet in the early afternoon to allow time for a casual spin ride hugging the shore of the Fox River and offering beautiful views of St. Norbert College, popular local fishing spots, the De Pere historic locks and dam, and quintessential Wisconsin countryside. We will reconvene in the early evening for dinner as a group. Lodge Kohler, our AAA Four Diamond home for the night, is home to a rooftop bar overlooking Lambeau Field, and a fine restaurant.
Day 2
40–50 miles, gently rolling hills and flat terrain
After a breakfast at Lodge Kohler, we will head into the heart of Door County. Our day’s ride will start in an area of Door County known as Southern Door and will take us north through gently rolling fields through the heart of what was once the largest concentration of Belgian communities in the New World. Along the route, see beautiful barns, rolling fields, and the ever-present water views of Green Bay.
The morning ride ends at Door County’s jewels, Potawatomi State Park, where we will enjoy a delicious picnic on the banks of Sturgeon Bay. The park is named for one of the tribes that inhabited Green Bay’s shores when the Europeans first arrived. They called themselves Bo-De-Wad-Me, meaning “keeper of the fire.” The tribal name and spelling were changed over time on maps to become Potowatomi. Walk one of the many shaded birch-lined trails. Watch the deer graze and hawks soar above the tree lined lakeside cliffs that form the western edge of the Niagra Escarpment stretching from Wisconsin to New York. Or, just take in the panoramic view from atop a 75-foot observation tower. On clear days, you can see 16 miles across the majestic waters of Green Bay from its 225 feet high vantage point above the water.
We end our day today in the charming town of Sturgeon Bay. Named Wisconsin’s friendliest small town, Sturgeon Bay is the county seat of Door County and the only city on the peninsula. Settled in 1835, its economy originally was based on lumbering. That changed, however, when the canal linking Green Bay and Lake Michigan opened to shipping in 1881 and altered the economy of the town of Sturgeon Bay.
We will spend our evening at the Stone Harbor Resort on the shores of Sturgeon Bay. Savor the sunset views before dinner on your own this evening at one of the many charming options in town.
Day 3
30–40 miles, gently rolling hills and flat terrain
Our morning starts with a ride heading east along the shipping canal connecting Green Bay and Lake Michigan, before turning north along the shoreline of Lake Michigan. At this point, take a moment to see two of Door County’s eleven lighthouses. Many of Wisconsin’s early settlers came by Great Lakes steamships. These shipping lines eventually petitioned the US Government to commission lighthouses along the dangerous rocky shoreline of Lake Michigan.
Our ride continues, winding along the lake shore, catching glimpses of the water between unique waterfront homes and cottages. Spend a few miles spinning lakeside, and then head inland to ride through some of Door County’s many orchards. We will be visiting during the heart of Door County’s cherry season. Roads sprinkled with cherry trees greet us with shiny red globes of fruit peeking out from beneath the green leaves. We might even see some harvesting in progress with mechanized “tree shakers” able to harvest 4 trees per minute!
We will lunch this afternoon at a local winery, where you can choose to stay and sample wines, possibly including a vintage or two of cherry wine. Or, you may continue pedaling to the picturesque town of Fish Creek, our home for the next three nights. The afternoon is yours to explore nearby Peninsula State Park, charter a fishing boat to try your hand at catching the local walleye, pike, trout or salmon, or wander the flower box lined streets and shops of charismatic Fish Creek.
Our home in Fish Creek is the elegant White Gull Inn. Settle in prior to enjoying dinner on your own at one of the many options Fish Creek has to offer.
Day 4
40–75 miles, gently rolling hills and flat terrain
Today is a cyclist’s dream day! We make our way to the largest island in Door County, Washington Island. Once home to large fishing operations, the island now houses only 650 residents year-round creating an ideal cycling destination filled with miles of quiet roads. Opt to bike or shuttle to the 30-minute ferry that will take us to the island across the strait after which Door County was named. Originally named by early French explorers as Porte Des Mortes, meaning “Door of Death”, the strait was known for its treacherous currents and climate which caused many early navigators to be lost in the strait. Upon our safe arrival on the island, we will spin along empty scenic roads, catching views of the lake, surrounding islands, and sleepy island villages. Watch for fishing pelicans soaring above the water as we pedal the roads along the rocky shoreline.
After lunch in the early afternoon at one of the local gourmet eateries, we will make our way back toward Fish Creek via the road network winding its way through Northern Door County. The “Top of the Thumb” is highlighted by the communities of Ellison Bay, Rowleys Bay and Gills Rock. These charming villages are home to an abundance of small museums, artists’ galleries, shops and restaurants. In between is quintessential Door scenery. We will reconvene this evening to recount the day’s adventures and tell stories of our successful navigation through the “Porte Des Mortes” prior to dinner on your own in yet another wonderful option in Fish Creek.
Day 5
15–57 miles, gently rolling hills and flat terrain
We begin our day today with yet another bountiful White Gull Inn breakfast – perhaps their award-winning cherry stuffed French toast! Today is a day to take advantage of the spectacular views offered in nearby Peninsula State Park. Gentle climbs are rewarded by bluff top views of sparkling Lake Michigan and descents to the sandy beaches along the shoreline. There is an option to continue pedaling a short distance to lunch in the quaint fishing town of Bailey’s Harbor. Named for a ship captain who took refuge from a violent 1840’s storm in the natural cove which defines the village waterfront, the appealing town of Bailey’s Harbor has a mix of shops and galleries to explore. Along our route returning to Fish Creek, take a minute to stop at the Edgewater Gallery sculpture garden – a worthwhile stop even if art is not “your thing.” The late afternoon is yours to enjoy strolling the charming streets of Fish Creek before we finish our evening with dinner as a group.
Day 6
25–45 miles, gently rolling hills and flat terrain
Our final day returns us to Green Bay. After a brief van shuttle, we will bike from Brussels, WI all the way back to Lodge Kohler on a mix of low traffic roads and paved paths. Scenery includes the shore of Green Bay and pastoral Wisconsin farmland. Lodge Kohler will provide rooms for showers and a champions’ lunch prior to departure.
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
Night 1
Lodge Kohler, 1950 S. Ridge Rd, Green Bay, WI 54304.
Just 100 yards from Lambeau Field at the center of redeveloping Titletown neighborhood of Green Bay, Lodge Kohler offers sumptuous rooms, a fabulous spa, an indoor/outdoor restaurant and café, and a rooftop bar. Bathroom fixtures are a showcase for Kohler’s latest options.
This full service lakeshore resort has a full range of amenities, including indoor and outdoor pools, tiki bar, and beautiful lake views.
Night 2
Stone Harbor Resort, 107 North First Ave, Sturgeon Bay, WI 54235. | (920) 746-0700.
This full service lakeshore resort has a full range of amenities, including indoor and outdoor pools, tiki bar, and beautiful lake views.
The beautiful accommodations of the White Gull Inn are walking distance to everything in the heart of charming Fish Creek.
Nights 3, 4 & 5
The White Gull Inn, 4225 Main Street, Fish Creek, WI, 54212.
You won’t want to leave this Select Registry inn, which is why we are staying for three nights! The beautiful accommodations are walking distance to everything in the heart of charming Fish Creek.
And:
The Main Street Motel, 4209 Main Street, Fish Creek, WI 54212.
An alternative lodging option, this quaint, meticulously maintained family owned property offers some additional room types and a small discount in the tour price.
Get Prepared!
Cycling
The terrain is a mix of gently rolling hills 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 – 50+ miles each day (at your option). 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
Lodge Kohler, 1950 South Ridge Road, Green Bay, WI 54304 855-395-7638
Getting to the Tour Start (Green Bay e, WI):
Driving: Approximate travel distance to Green Baye–
- Minneapolis, MN: 283 miles
- Madison, WI: 132 miles
- Milwaukee, WI: 115 miles
- Chicago, IL: 206 miles
- Indianapolis, IN: 393 miles
Airports:
Austin Straubel International Airport (GRB) is served by American, Delta and United, with connections to Atlanta, Chicago, Detroit and Minneapolis.
Ground Transit:
Uber, Taxi, limo, and shared sedan service is available to and from the airport.
http://www.flygrb.com/parking-transportation/ground-transportation
Parking: We have arranged for long term parking there for the duration of your tour. We will end the tour at the same inn with an opportunity to shower there prior to departure.
Arrival/Departure Timing
Arrival time on the first day of the tour is no later than 11:00 a.m. if renting equipment from us, or 11:30 a.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. on the last day of the tour. Your return flight should be no earlier than 5:00 p.m. that evening.
Extend Your Vacation
There is a lot to do in and around nearby Green Bay if you have time. The downtown riverfront district hosts festivals and farmers markets each weekend in the summer and is home to numerous Wisconsin craft breweries! http://www.greenbay.com/visit_us/
Everyone also knows that Green Bay is “Titletown” and home to the Green Bay Packers. A trip to the Green Bay Packers Hall of Fame and Lambeau Field is a must even for those whose first love may not be football!
We plan to wrap up around 3:00 p.m. Your return flight should be no earlier than 5:00 p.m. that evening.
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?
Begin your journey with a visit to Lambeau Field, home of the Green Bay Packers, and explore the rich history of this iconic sports venue
Enjoy a leisurely spin ride along the picturesque Fox River, past St. Norbert College and historic locks and dams
Pedal through Door County's cherry orchards during cherry season and indulge in a delightful lunch at a local winery
Embark on a ferry ride to Washington Island and enjoy a cycling adventure along quiet roads with numerous Lake Michigan views
Discover the natural beauty of Peninsula State Park with its bluff-top views of Lake Michigan and a scenic ride to the quaint fishing town of Bailey's Harbor
See What Our Customers Say About Us
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.
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.
