Nestled amidst the verdant landscapes of upstate New York, we take you on stunning Finger Lakes bike rides in a region full of natural wonders and cultural treasures. Here, the highest waterfalls east of the Rockies cascade gracefully amidst lush glens and rolling hillsides adorned with vineyards. Cycling in the Finger Lakes through winding country roads, you’ll encounter charming colleges, picturesque hamlets, and quaint valley farms, each adding to the region’s allure.
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.!
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Trip Overview
Price
Early bird discount: $2725 per person
Full price: $2825 per person
Bicycle rental : $100
Single room supplement: $650
Upcoming tour dates & status
- 7/13/25 – 7/18/25
- 7/20/25 – 7/25/25
Meeting/Departure Point
Ithaca, NY
Nearest Airport
ITH Ithaca Regional Airport
Duration
6 days, 5 nights
Tour difficulty
Rolling hills and a few strenuous climbs
Included
- Lodging:
5 nights at boutique, lakefront inns. - Meals:
Dinner on nights 1, 2, 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.
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
20–35 miles, hilly
Meet the group just outside Ithaca on the relaxing campus of La Tourelle Hotel and Spa. Following bike fittings, lunch and orientation, we will take our first ride in the Finger Lakes. Expect some hills, but also a few stretches of relatively flat riding along valley roads through quaint country crossroads. We’ll end up back at La Tourelle for dinner together onsite.
Day 2
42–54 miles, hilly
Our second day of bicycling will take us through downtown Ithaca and around the southern tip of Cayuga Lake. We’ll climb away from the lake briefly on rolling farmland toward the highest waterfall in the Finger Lakes region. We will follow country roads that lead us to the shore of Seneca Lake where we’ll pass through Watkins Glen. Time permitting, hike a spectacular gorge with numerous waterfalls and cliffs. It’s a short distance from Watkins Glen to the Inn at Glenora Winery, our lodging for one night. Relax at sunset in the Adirondack chairs gracing your private balcony overlooking the vineyard and Seneca Lake. Take the opportunity to tour and taste at the award winning winery. We will dine this evening as a group on the wonderful cuisine at the vineyard restaurant.
Day 3
30–64 miles, hilly
Rise early for a big day on the bike and some of the best lake views of the tour! Start with a big climb away from Seneca Lake, or leapfrog ahead in the van to start your ride at a high spot. We’ll make our way over to charming Hammondsport on the southern tip of Keuka Lake. Pause in the quaint town square for a little ice cream. Continue north along a road that tightly hugs the shore of Keuka Lake with numerous opportunities to soak up the sparkling water views. Lunch will be a picnic at a waterfront park on the north end. Our destination at the end of the day is Geneva On The Lake, an elegant, old world resort on the north shore of Seneca Lake. You may want to venture into the charming downtown of Geneva or opt to take advantage of the many wonderful amenities of this special inn: a 70 foot swimming pool, formal gardens, a 10 acre estate overlooking Seneca Lake and, in late afternoon, a ride on the inn’s 24 foot pontoon boat. We will dine as a group tonight on the moon-lit patio of the inn, weather permitting.
Day 4
34–75 miles, hilly
We bike today from Geneva to Skaneateles, our home for the next two nights. The terrain will be flatter now that we are at the northern end of the Finger Lakes. We leave Seneca Lake behind today, pedaling on to the charming riverfront town of Seneca Falls, whose Main Street claims to be the inspiration for the town of Bedford Falls in the movie, “It’s A Wonderful Life.” Take a few minutes to explore the Women’s Rights National Historical Park, where the first Women’s Rights Convention was held in 1848. After lunch, opt to continue biking to Skaneateles, a beautiful small town on the northern shore of Skaneateles Lake. Stroll the lakefront park, or the many shops and boutiques dotting the downtown area, before dinner on your own with numerous wonderful options within walking distance of our inn. .
Day 5
32–63 miles, hilly
Our “Layover Day” in Skaneateles affords you the option not to bike today, or to bike a distance of your choosing. We will support a loop ride around Skaneateles Lake of up to 62 miles, with options to cut this distance in half. You will enjoy walking the sidewalks of this quaint town with plenty of shops and restaurants. Rent a kayak or sailboat and explore Skaneateles Lake, said to be New York’s clearest. Or, opt to visit one of the wineries on the outskirts of town for additional samples of Finger Lakes wine! As a special treat, we have chartered a private boat cruise this afternoon prior to dinner. Dinner this final evening is as a group.
Day 6
40–53 miles, hilly
We say goodbye to Skaneateles this morning as we make our way west to the shore of Cayuga Lake. Our final day of the tour offers a beautiful rural ride south to Ithaca. The ride will start with flat terrain, then get hillier as we approach the southern end of the lake. We’ll return to our Ithaca hotel in time for a final catered lunch and pre-arranged showers.
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 and Optional Lodging Before or After the Tour
La Tourelle Resort and Spa “Our beds are comfy, the grounds are beautiful, and the hike to Buttermilk Falls is simply inspiring. Nestled on 70 acres, we are just minutes from Cornell University and Ithaca College, as well as exquisite wineries, fascinating museums, great music and theater venues, and mouth-watering restaurants. Ask our staff for recommendations – we just love sharing our favorite places to dine and explore.”
Night 2
Inn at Glenora Don’t just tour a winery, spend the night there! Rooms are beautifully appointed with Stickley furniture and brand new pillow top mattresses and box springs. Every room features a private balcony or patio with a view of the vineyard, Seneca Lake and the opposing hillside.
Night 3
Geneva On The Lake is located on 10 beautiful acres, the inn has received the coveted AAA Four-Diamond Award for 24 years and is listed on the National Register of Historic Places. The terrace, formal gardens, classical sculptures, 70 foot pool and boathouse enhance the old-world charm that awaits you.
Nights 4 & 5
Packwood House / Sherwood Inn Select Registry inn overlooking the lake and walking distance to numerous shops in this friendly town. The Sherwood Inn has been welcoming travelers since 1807.
Get Prepared!
Cycling
The terrain is a mix of rolling hills and a few challenging climbs, making it appropriate for intermediate and advanced riders. Daily distances of 40-65 miles inn to inn. Typical daily cumulative climbing will be in the 1,000 – 2500 feet range. As with all Carolina Tailwinds tours, there will be multiple opportunities for “leap-frog” shuttles to shorten and/or flatten the route. Or, bike inn to inn everyday without ever getting in the support van. Road bikes and lightweight hybrid bikes with a wide range of gearing are recommended.
Tour Point of Origin
La Tourelle Resort and Spa, 1150 Danby Rd, Ithaca, NY 14850. (607) 273-2734
Getting to the Tour Start:
Driving: Driving distance to Ithaca–
- Philadelphia, PA: 234 miles
- Columbus, OH: 334 miles
- Boston, MA: 351 miles
- Albany, NY: 184 miles
Airports:
Ithaca/Tompkins Regional Airport (ITH) http://flyithaca.com/
Served by American, Delta & United.
Located minutes from our tour start/end location.
Ground shuttle to the tour start is available.
Syracuse/Hancock Internat’l Airport (SYR) http://www.syrairport.org/
Served by several major and regional airlines.
Located 47 miles from the tour start/end location.
Elmira Corning Regional Airport (ELM) http://www.ecairport.com/
Served by Delta, United, and Allegiant Air.
Located 41 miles from the tour start/end location.
Greater Rochester International Airport (ROC) http://www.monroecounty.gov/airport-index.php
Served by several major and regional airlines.
Located 99 miles from the tour start/end location.
Ground Transit:
Ubers, Taxis and rental cars are available at Ithaca and the other airports.
Arrival/Departure Timing
Arrive at the tour start location no later than 9:45 a.m. on Day 1 (8:45 a.m. if renting a bicycle.) Arrive a day or more early to explore Ithaca on your own.
We will return to Ithaca on Day 6 between 2 and 3 p.m.
Extending Your Stay
Consider a visit to Corning, NY. The Corning Museum of Glass is fascinating and takes several hours to tour.
Ithaca, NY is a bustling college town (Cornell and Ithaca College). Set on a steep hillside leading to Cayuga Lake, it has a vibrant downtown.
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?
Cycle through picturesque landscapes dotted with serene lakes, including Cayuga Lake and Seneca Lake
Walk past 19 waterfalls in two miles on the enchanting Gorge Trail at Watkins Glen
Marvel at the beauty of the highest waterfall east of the Rockies
Treat your palate to delicious Finger Lakes wines, especially award winning dry Rieslings
Unwind in luxurious accommodation, where you can enjoy upscale amenities, scenic views, and leisurely activities like pontoon boat rides and swimming in a 70-foot pool
See What Our Customers Say About Us
…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.
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.
