Few places in the United States have the same kind of timeless charm as the Finger Lakes region of upstate New York, because few areas have existed as long. A series of glacial lakes formed more than two million years ago, and today these 11 iconic bodies of water continue to beckon vacationers from around the country.
Although boating and water sports have always been popular in the summer, the Finger Lakes’ reputation as a wine-producing region now draws visitors into the fall. Many of the region’s 11,000 acres of vineyards are situated on hilltops overlooking the lakes, and the topography is comparable to Germany’s Rhine River valley — part of the reason Riesling is among the most popular varietals produced in the Finger Lakes.
Photo courtesy Heart and Hands Wine Company, located on the eastern shore of Cayuga Lake.
Although it’s New York state’s largest wine-growing area, the Finger Lakes region is also home to a growing number of craft breweries and cideries. Produce stands and dairy farms abound, providing fruits, vegetables, and cheeses for the region’s fine farm-to-table restaurants as well.
A quick Tradewind Aviation charter flight from New York, Connecticut, Boston, Philadelphia, Washington, D.C., Pittsburgh, and more cities will bring you to the heart of the Finger Lakes for a weekend of fall foliage, outdoor activities, fine dining and, of course, wine tasting.
Ensure that you have safe ground transportation on your wine tasting tour by hiring a driving service. The Finger Lakes area is rural, so ride sharing apps like Uber and Lyft aren’t reliable. This great transportation list highlights an array of options depending on your budget, whether you wish to ride in a limousine, coach, or car.
FRIDAY
Photo courtesy Lake House Canandaigua. An exterior shot of their charming, historic property with 125 guest rooms and suites.
3 p.m. Fly directly into Canandaigua Airport to save yourself the hour-long drive from Rochester. Your home base for the first half of your trip, The Lake House Canandaigua, is just a 10-minute drive away. Members of the region’s prominent Sands family, founders of the Canandaigua Wine Company (now Constellation Brands), opened the hotel in August 2020 after an extensive renovation to an existing lakefront motor lodge. The majority of the hotel’s 124 rooms boast views of Canandaigua Lake, and the balconies and living areas in the main building’s lakeside suites provide extra room for admiring the vistas.
6 p.m. Settle into your room, then it’s out for a walk to explore the Lake House’s kitchen garden and outdoor sculpture collection. Head to the property’s iconic Sand Bar, which has been operating since 1994, for a pre-dinner drink. Watch sailors and boaters dock for the day as you sit under the shade of an umbrella and sip a fresh cocktail. Enjoy dinner on property at Rose Tavern, the Lake House’s rustic New American eatery. Menu highlights include local beef tartar, farmstead cheese and charcuterie board with local honey, and the Hudson Valley duck breast entrée. Though the wine list has options for lovers of French or Italian vintages, take advantage of the extensive selection of New York bottles to get a taste of what’s to come. Adventurous drinkers might enjoy Barry Family Cellars Leon Millot “Pet Gnat,” a dry Lambrusco.
SATURDAY
9 a.m. A full day of wine-tasting requires a hearty breakfast. Head to Main Street in Canandaigua’s historic district for crêpes, breakfast tacos, or biscuits with wild berry compote at Simply Crêpes. Explore the stretch of shops and restaurants before starting the day’s main activity: Beer and wine tasting.
12 p.m. Beer enthusiasts won’t want to miss the opportunity to visit acclaimed craft brewery Other Half’s outpost in Bloomfield, just a 10-minute drive from the Lake House. Wine-drinkers should start their loop of Canandaigua Lake with Heron Hill Winery (reservations required). Its tasting room is housed in a renovated 100-year-old barn that overlooks the vineyard’s rows of Riesling and Cabernet Franc. After a tasting, find a spot at a picnic table to relax before moving on to your next stop. Should hunger strike, Heron Hill serves wood-fired pizzas starting at 12 p.m. on Saturdays.
Flickr user: Valerie Knoblauch Canandaigua, New York, CC BY 2.0, via Wikimedia Commons
2 p.m. A scenic drive to the southern end of Canandaigua Lake will bring you to the village of Naples, where Inspire Moore Winery has been operating since 2006 (reservations highly recommended). It’s been producing Riesling and Syrah since the start, but more recent additions to the winery’s collection include Pinot Noir and Blaufrankisch, the latter of which earned a “Best of New York State” designation.
4 p.m. End the day of tasting on a lighter note by continuing up the east side of Canandaigua Lake to Star Cider. The tasting room, which opened in 2019, has ample space to spread out both indoors and outdoors. Choose from its menu of signature ciders and seasonal specials, or sip on a cocktail such as the Seneca Orchard Mimosa.
Photo courtesy F.L.X. Table in Geneva, New York. A mouthwatering cheese and local produce plate brightens a log cutting board.
7 p.m. After a brief rest at the hotel, it’s time for dinner. Those who don’t mind a bit of a drive won’t want to miss F.L.X. Table, a tiny fine-dining restaurant in nearby Geneva. Reservations are hard to come by with just 12 seats total, but the prix fixe menu, which focuses on local ingredients wherever possible, has won national acclaim.
10 p.m. After a full day of activity, end the evening with fireside s’mores back at the Lake House.
SUNDAY
9 a.m. Before heading to the next destination on your road trip, end your time at the Lake House with breakfast at Rose Tavern. Lobster eggs benedict, avocado toast, and warm oats with apples and maple sugar are Sunday brunch favorites.
10:30 a.m. The day’s meandering route will take you first to the town of Geneva, located on the north end of Seneca Lake. A stop at Billsboro Winery is a must: Its 19th-century restored barn tasting room sits on 28 acres overlooking the lake (reservations recommended). Opt for the wine and chocolate tasting, which pairs Billsboro’s Finger Lakes wines with bites from a local chocolatier.
12 p.m. The route to Cayuga Lake, the next stop on your trip, takes you through Seneca Falls, the birthplace of women’s rights in the U.S. and home of the 1848 Seneca Falls Convention. Break up the day with a visit to the National Women’s Hall of Fame and lunch in the historic hamlet.
2 p.m. Round the north end of Cayuga Lake and head south towards Aurora, your home for the night. But first: Heart and Hands Wine Company, one of the region’s best known and finest wine producers (reservations highly recommended). It makes just 2,000 cases of wine a year from its own Estate Vineyard and other vineyards around the region. Select a flight of Pinot Noir, Riesling, and Chardonnay to enjoy in its hilltop tasting room.
The newly opened Spa at the Inns of Aurora features a beautiful, farm-inspired building and stunning views of Cayuga Lake.
3 p.m. After your tasting, drive just 10 minutes south to check into one of five historic properties that comprise the Inns of Aurora. Pleasant Rowland, alumna of Aurora’s Wells College, founder of American Girl, and owner of Aurora home brand Mackenzie-Childs, has been painstakingly restoring historic properties in the town since she purchased the circa-1833 Aurora Inn in partnership with Wells College in 2001. The afternoon would not be complete without a visit to the newly opened farm-inspired Spa at the Inns of Aurora, which sits on a hilltop above town and offers sweeping views of Cayuga Lake. Designed by Hart Howerton and opened in June, the spa offers body and skincare treatments, massage therapy, and energy work in partnership with local company Rasa Spa.
7 p.m. After a day of travel, enjoy dinner at 1833 Kitchen & Bar at the Aurora Inn, either in the cozily furnished dining room or on the patio overlooking the expansive lawn and Cayuga Lake. The Bibb lettuce salad, Faroe Island salmon, and spaghetti Bolognese are not to be missed, and the seasonal crisp is a perfect sweet finish to the meal.
MONDAY
The Taughannock Falls 215-foot waterfall in Ulysses, NY. Photo courtesy Tyler Finck.
10 a.m. After an indulgent weekend, grab a light breakfast from The Village Market before you check out of the hotel, then finish your road trip and weekend with some outdoor activity. With its 215-foot waterfall, Taughannock Falls State Park on the other side of the lake is a stunning example of the region’s famed gorges. The trail to the falls is just 1.5 miles round trip, so it’s suitable for all levels of hikers.
Finish the weekend by grabbing a quick lunch in Ithaca’s charming downtown before heading home. Options abound, but acclaimed vegetarian eatery Moosewood is a classic choice.
At the nearby Ithaca Airport, your private Tradewind Pilatus PC-12 awaits to transport you back home.
To learn more about booking your Finger Lakes vacation, please visit our website or contact our specialists at charter@flytradewind.com or at 1-800-376-7922. To receive a private charter quote, please complete our charter request form. To learn more about Tradewind’s comprehensive safety plan, please visit our COVID-19 Response page. For the latest travel updates, please visit our Travel Advisory page.