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: $2850 per person
- Full price: $2950 per person
- Bicycle rental : $100
- Single room supplement: $625
Upcoming tour dates & status
- 5/25/25 – 5/30/25
- 6/1/25 – 6/6/25
- 9/7/25 – 9/12/25
Meeting/Departure Point
Delafield, WI
Nearest Airport
MKE Milwaukee Mitchell International Airport
Duration
6 days, 5 nights
Tour difficulty
Rolling hills and a few short climbs
Included
- Lodging:
5 nights at boutique inns. - 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 from Milwaukee:
Carolina Tailwinds picks up on the morning of Day 1 and drops off in the late afternoon on Day 6 at the Milwaukee, WI airport (MKE). Timing is formally coordinated 2 weeks prior to 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
23–42 miles, hilly
We meet in Delafield, the gateway to south central Wisconsin’s beautiful Lake Country. Nestled along the shore of Lake Nagawicka in the Kettle Moraine hills, Delafield has a quiet charm all its own. Its historic downtown is a pleasant blend of housing, specialty shops, award-winning restaurants, and day spas. Historic sites include Hawks Inn, a colorful frontier stagecoach stop, and the campus of St. John’s Northwestern Military Academy, the oldest military academy in Wisconsin.
After bike fitting and a quick lunch, we’ll begin our ride on gorgeous roads bordering the small lakeshores typical of this region. We make our way into the country for a taste of the week to come – miles of serene rural riding in the heart of Wisconsin’s Dairy Land.
We regroup this evening at The Delafield Hotel, our home for this evening. Settle in and savor this celebrated boutique hotel’s many amenities in suites that offer their signature blend of contemporary and cozy vibes. We will meet for dinner as a group this evening at a local favorite.
Day 2
31–68 miles, hilly
We reluctantly leave Delafield behind today as we make our way west to land dotted with rolling ridgelines, open prairie, and small lakeside communities. Glacial forces carved this gorgeous landscape, forming the gentle hills, sparkling lakes, and clear river streams that continue to captivate visitors. We will stop for a catered lunch at Aztalan, one of Wisconsin’s most important archaeological sites. Explore the grounds that were home to the ancient middle-mississippian culture that thrived here in 1000 A.D. before heading out on the bike to continue on our journey to Madison.
We end our ride today by entering the city on one of the many awesome paved bicycle paths that wind their way through this bustling college town and state capital. The Edgewater Hotel is our end destination and is situated in the heart of the city with views of both the resplendent Capitol Dome and the shores of Lake Mendota. Enjoy the first blush of sunset over the lake on the Hotel Terrace before dining as a group tonight at a local favorite steps from our hotel.
Day 3
22–47 miles, hilly
Today is a day to take in all that makes Madison, Wisconsin such a special summer destination! After breakfast at The Edgewater, we begin the day with a stroll up to the beautiful Capitol for a group tour of this amazing building. We pop out on the upper levels of the Capitol Dome on this tour for some awesome views of the city and surrounding lakes.
After this tour, we head back to The Edgewater to regroup for our late morning spin ride around the shores of Lake Monona. Stand up paddle boarders, sailors and kayakers dot the lakes as we pedal by. We end in the early afternoon with a local classic ride through The Arboretum in the heart of the City along the shores of Lake Wingra. The Arboretum was established in 1932 as part of the University of Wisconsin Madison with an evolving mission specializing ecological restoration.
After this morning’s spin, you have some choices: stop, explore and learn a little more about The Arboretum and the horticulture history in the visitor center there, continue on a longer (guided and supported) ride into the countryside, where you will find pastoral views of rolling farm fields dotted with Holsteins and iconic red barns, or head back to The Edgewater to spend the afternoon on your own exploring the campus of UW and vibrant State Street, the pedestrian avenue which embodies the soul of the city. Hundreds of shops, galleries and restaurants line this street that connects the University of Wisconsin campus to the Capitol region of downtown.
Lunch today is on your own in order to maximize your flexibility. Grab a bite from one of the many food trucks downtown, or head to the iconic Union Terrace overlooking Lake Mendota.
At the end of the day, we invite you to join us for a beverage of choice on the Edgewater’s new lakeside terrace before dinner on your own tonight. Numerous farm-to-table options are within walking distance of the inn.
Day 4
40–73 miles, rolling hills
The work and inspiration from Wisconsin’s famous native son, Frank Lloyd Wright, can be seen throughout the cities and countryside of south central Wisconsin. We begin our day after breakfast with a short shuttle to Frank Lloyd Wright’s personal home and studio, Taliesin. A private guided tour awaits us of the Taliesin estate, truly one of the architecture world’s great treasures. Even those not generally interested in architecture will be fascinated by the quirky and imaginative rooms that Wright built and lived in for 50 years.
We spin our way after our tour through the prairie edge of the Wisconsin River Valley to the natural beauty of the Wisconsin Heights. Craggy hills rise above the fertile valleys through which we bike. We land early afternoon in the whimsical town of Mount Horeb. Norwegian heritage, artists, hipsters and farmers all can be found in this pleasant but decidedly urban feeling village. We will pedal along the main drag known as “Trollway,” complete with a collection of carved Scandinavian wooden trolls – some gardening, some biking, some eating – but all welcoming us to the heart of the town. Explore the streets dotted with specialty shops before dining on the delicious gourmet pizzas and great pub fare of The Grumpy Troll Brew Pub. Should you wish, pop into the Fisher King Winery for a sip of Wisconsin’s local wines.
Spend the remainder of the afternoon in vibrant Madison before we gather as a group to savor yet another of Madison’s infinite number of fresh local foodie restaurants for dinner together.
Day 5
42–56 miles, rolling hills with a few steep hills
After our last breakfast on the shores of Lake Mendota, we head out on a brief morning shuttle from bustling Madison. Our morning ride today spins toward Lake Geneva on empty backroads seemingly created for road cycling enthusiasts! Rolling wooded terrain interspersed with ridgetop views of the surrounding open pastureland dotted with cows provides perfect views of quintessential Wisconsin. New additions to our landscape today include the miles of solar farms being constructed that we will pass along our route.
We have lunch today along the shores of Lake Geneva. Historically, this community has been a summertime playground for Chicago’s wealthiest families which can be seen in the grand palatial homes that surround this beautiful lake. The lake itself is spring-fed, which accounts for the crisp, clean, clear water.
We stop after lunch at the fascinating Yerkes Observatory for a private group tour. This facility was established as part of the University of Chicago in 1897 and houses still the world’s largest refracting telescope. The tour is more than a guided lesson through the big names in 20th century astronomy – it also includes history of the area, the fascinating architecture of this facility and an opportunity to stroll the Olmstead designed grounds.
We end the day with an optional ride to the Geneva Inn, our home for the night. Opt to explore along the way some of the boutique shops in town, stroll along the scenic lakeshore to catch a glimpse of the beautiful homes, or simply relax in your lakefront room savoring the peaceful water view from The Geneva Inn just outside this bustling town.
Join us for happy hour on the lake before dining as a group on the lovely cuisine of the Geneva Inn.
Day 6
32–46 miles, rolling hills
We begin our last day together with a final breakfast as a group overlooking the shores of Lake Geneva. We pedal away from the inn after breakfast in the gorgeous morning light to the rural roads you have come to expect in America’s Dairyland. New today is the terrain of the southern end of the Kettle Moraine, a landscape shaped by the glaciers that covered the region thousands of years ago. Forests and bogs rise from the prairie and welcome us along our shady route back to Delafield. Lunch and showers await before 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
The Delafield Hotel
With sophisticated elegance and classic old-world charm, The Delafield Hotel is a sought-after, full service boutique hotel just outside of the Milwaukee area. Is is one of only ten properties recognized as Four Diamond in the state of Wisconsin and the specialty shops and stores of quaint downtown Delafield are just steps away from the hotel front doors.
Nights 2, 3, & 4
The Edgewater
Located on the shores of Lake Mendota, The Edgewater is just down the street from the Capitol Square, the heart of downtown Madison. It’s within walking distance of State Street and its eclectic restaurants and shops. The hotel offers over 200 guest rooms, an outdoor plaza and pier, several restaurants and lounges, a luxurious spa, and extraordinary facilities for meetings, events, and weddings.
Night 5
The Geneva Inn
Located on the scenic shores of Geneva Lake, The Geneva Inn is home to panoramic lake side views from our hotel and restaurant. With charming accommodations, attentive staff and award winning cuisine, The Geneva Inn is one of the most sought after year round retreats in Lake Geneva, Wisconsin.
Get Prepared!
Cycling
The terrain is a combination of gently rolling terrain, hills, and, in a few spots, challenging climbs. As with all Carolina Tailwinds tours, less ambitious cyclists can take advantage of short cuts and strategic “leap frog” van shuttles along the route to tailor the route to their needs.
Tour Point of Origin
The Delafield Hotel, 415 Genesee St, Delafield, WI 53018 262.346.9311
Getting to the Tour Start (Delafield, WI):
Driving: Driving distance to Delafield, WI From:
- Chicago: 115 miles
- Minneapolis: 311 miles
- Cincinnati: 414 miles
- Nashville: 590 miles
- Washington: 808 miles
- Charlotte: 873 miles
Airports:
Milwaukee Mitchell International Airport (MKE) https://www.mitchellairport.com/
Service by all major airlines.
32 miles from tour start/end location in downtown Delafield.
Most airlines recommend that you arrive at the airport 1 1/2 to 2 hours before your flight’s scheduled departure time.
Ground Transit:
Taxis, Uber/Lyft and rental cars are available at the airport.
A complimentary Carolina Tailwinds shuttle will be available to and from the airport at one designated time on the morning of Day 1 and the afternoon of Day 6.
Parking: We have arranged for long term parking at The Delafield Hotel 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
Arrive at the tour start location no later than 11:00 a.m. on Day 1 (10:30 a.m. if renting a bicycle.) Arrive a day or more early to enjoy all that Milwaukee and Delafield offer on your own. We will return to Delafield on Day 6 by 2 p.m.
Extend Your Stay
Milwaukee is a vibrant, effortlessly cool town that is full of fun things to see and do. Sample the mind-blowing culinary creations of the city’s world-class dining scene. Experience the spine-tingling roar of a Harley-Davidson up close at the iconic Harley-Davidson Museum. Take in a stunning performance in the Milwaukee Theater District. And celebrate just about anything at one of the city’s more than 100 festivals. The only way to grasp the beauty of our great place on a Great Lake is to experience it for yourself. https://www.visitmilwaukee.org/about-milwaukee/
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?
Enjoy the ultimate bike tours in Madison, WI, and explore scenic lakes, rolling hills, and glacial landscapes
Discover iconic landmarks, including Frank Lloyd Wright’s Taliesin and the Yerkes Observatory
Enhance your experience with private tours, from architectural wonders to ancient archaeological sites
Relax in boutique accommodations, from The Delafield Hotel to The Geneva Inn, offering cozy comfort and scenic views
Savor Wisconsin’s renowned farm-to-table cuisine, craft beers, and artisanal cheeses
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.
