NY Finger Lakes Tour

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Upstate New York Bicycle Tour

A Six Day Cycling Vacation of the Finger Lakes Region

The highest waterfalls east of the Rockies, cascades, glens, colleges, hamlets, valley farms, quaint towns and steep hillsides dotted with vineyards.  All of this, in addition to the sparkling waters of long blue glacial lakes, make the NY Finger Lakes a special bicycling destination not to be missed.  

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NY Finger Lakes

Ithaca, NY

Tour Difficulty

Rolling Hills and a few Strenuous Climbs


6 Days, 5 Nights


Ithaca, NY

Nearest Airport

ITH Ithaca Regional Airport


From $2725 per person


7/7/24 - 7/12/24 7/14/24 - 7/19/24 7/21/24 - 7/26/24

Tour Status

2024 dates are available for enrollment!
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This was a wonderful vacation. It was our first experience with this type of cycling holiday. The trip was exactly as advertised and more. Not once were we ever made to feel that we had overestimated our abilities. The combination of the hosts, the guests, the scenery and the lodgings all came together to make this an unforgettable adventure. We would not hesitate to recommend this tour or this company to anyone. We do plan on joining them for one of their other tours in the future.
Bob, St. Marys, ON

ItineraryDownload Itinerary

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 a 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 leap frog 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 Historic 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 dining as a group this evening at a local gourmet favorite.

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 evening is on your own with numerous wonderful options within walking distance of our inn.

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.


$2,725 - $2,825
Bike Rental
Single Room Supplement

Low end of tour price range reflects the 6 month Early Bird Discount, applied when you enroll and pay in full 6 months or more prior to your tour date.  High end of price range reflects no Early Bird Discount. 

Prices are subject to change at any time.

What's Included in Your Tour Price


5 nights at boutique, lakefront inns


Dinner on Nights 1, 2, 3, & 5; All lunches except 1; All breakfasts; snacks; and hors d'oeuvres most nights.

Services of Expert Guides

Carolina Tailwinds maintains a guest to guide maximum ratio of 7:1 on all our tours.  Guides are ready to show you the hidden wonders of each and every destination.

Full Route Support & Luggage Transfer

Service of 1 – 2 support vans on route every day.

More details on what's included: 

Click here to go to another page.


La Tourelle Resort and Spa

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.

Inn at Glenora Wine Cellars

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.

Geneva on the Lake

Night 3

Geneva On The Lake   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.

Packwook House, Skaneateles, NY

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.



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


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 tour start/end location.

Elmira Corning Regional Airport (ELM)  http://www.ecairport.com/  
Served by Delta, United, and Allegiant Air.
Located 41 miles from 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 tour start/end location.

Ground Transportation:  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.

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