Still dreaming about sipping on Italian wines on the coastline this summer? What if we told you there was a way to do it without leaving the state’s borders.
Let us introduce to Penn Yan, NY, a little sliver of Italy that we like to call New York State’s “Little Tuscany”— and it only resides a couple of hours from NYC.
While summer in the city usually means beaches, rooftop bars, and long days in the sun, sometimes a quick trip upstate can offer something just as dreamy—minus the crowds and with a touch more wine.
In Penn Yan, a charming village at the northeastern tip of Keuka Lake, it’s all about countryside views, slow afternoons, and that golden hour glow.
Thanks to its hillside vineyards, boat-up tasting rooms, and rustic lakeside atmosphere, the region has earned the nickname “New York’s Little Tuscany.” And just one scroll through photos of vineyard patios and glassy water at sunset is enough to see why—the resemblance is spot-on.
During these warmer months, Keuka Lake invites you to kayak, paddleboard, or cruise across its Y-shaped shoreline, where certain wineries even let you dock your boat and walk straight into a tasting.
It’s the kind of place where you can spend an afternoon drifting in calm water, then toasting with crisp local riesling by dusk. And when fall rolls in, the hills erupt in shades of deep red and amber—turning the landscape into a full-on Tuscan fantasy.
The town of Penn Yan itself blends historic charm with lake life ease. You’ll find 19th-century brick façades, boutique shops, and cozy cafés perfect for a slow morning stroll.
At sunset, the western-facing hills of Keuka Lake reflect the glowing sky, setting the scene for a romantic picnic among the vines—or a glass of wine on the porch of a lakeside inn.
Throughout town, there are plenty of Italian-style touches to make the comparison feel more than fair. Some inns and wineries host evening “aperitivo hours” on patios with lake views, where you can sip wine with local cheese and watch the sky turn peach.
Places like Seneca Farms offer homemade ice cream and seasonal fruit toppings, while farm stands dot the roadside in the summer with fresh peaches, berries, and jam jars straight out of a countryside dream.
It’s also common to hear live folk or jazz music echoing from local wineries, especially on weekends, when string lights and vineyard views turn into festive, piazza-style evenings.
And just steps from Main Street, the Keuka Outlet Trail offers miles of scenic paths with waterfalls, stone ruins, and the occasional deer or osprey at sunrise.
Want to catch the views without breaking a sweat? Guided sunset boat cruises drift across the lake, pouring local wine and sharing stories about Keuka’s steamboat and winemaking past.