After a leisurely breakfast in Manhattan, pick up a rental car and head northwest-stop for a mid-morning stretch and coffee at Blue Bottle Coffee (Ferry Building) in the city before setting out on the drive upstate. Pause in the Hudson Valley for a scenic walk at Walkway Over the Hudson and a quick charcuterie lunch at Hudson-Chatham Winery's tasting room to sample regional wines en route, then continue toward the Finger Lakes with an afternoon arrival planned in time for checking into your lakeside lodging.
After checking into your lakeside lodging, take a gentle orientation drive along Seneca Lake and stretch your legs with a waterside stroll at Clarke Historical Museum Park before a late-afternoon tasting at Ravines Wine Cellars to sample their crisp Rieslings and chat with the winemaker. As twilight falls, enjoy a cozy dinner featuring local fare at The Red Dove Tavern, where farmhouse ingredients pair perfectly with Finger Lakes vintages and set the tone for tomorrow's full day of winery exploration.
As night settles, wind down with an intimate lakeside tasting at Dr. Konstantin Frank Winery's cozy tasting room, enjoying vinified Rieslings and an insider chat about Finger Lakes terroir; their knowledgeable staff often welcome late arrivals with small-plate pairings. Afterwards, savor a relaxed dinner with panoramic views at Stonecat Café, where seasonal comfort dishes and local cheeses complement the wines and set a warm, unhurried tone for tomorrow's full day of winery explorations.
Start the day with a scenic drive north along the lakeshore to Hermann J. Wiemer Vineyard for an in-depth tasting of their acclaimed Rieslings and a brief cellar tour that explains cold-climate vinification. From there, wander the snowy vineyard paths to Anthony Road Wine Company for a guided tasting that highlights experimental varietals, then warm up with a late-morning small-plate pairing at Boundary Breaks Vineyard's tasting room, where sweeping lake views accompany their terroir-driven red and white wines.
Spend a relaxed afternoon driving the scenic Seneca Lake Wine Trail with a cellar-door tour and tasting at Ravines Wine Cellars' sister property Lamoreaux Landing Wine Cellars, where you can sample their lake-cooled Chardonnays and tour the barrel room. Follow that with a winter-focused tasting flight and behind-the-scenes walk through production at Red Newt Cellars, then warm up with a cozy wine-and-cheese pairing on their heated patio while watching late light shimmer across the lake.
As twilight deepens, settle into a warm, convivial tasting at Fox Run Vineyards where their heated tasting porch and flight of reserve Rieslings and cool-climate Pinot Noir make for an unhurried introduction to Finger Lakes evenings. Follow that with a cozy, chef-driven small-plates dinner paired flight at The Belhurst Castle's wine bar, enjoying historic architecture and lake views as you reflect on the day's vineyard tours and plan tomorrow's Keuka Lake drive.
Begin with a hearty lakeside breakfast at Hand + Foot in Hammondsport, then take the short drive to Dr. Konstantin Frank's Keuka tasting room for a crisp Riesling flight and conversation about grafting and slope-driven microclimates. Continue with a mid-morning visit to McGregor Vineyard for a guided cellar tour and barrel-sample tasting, followed by a stroll through their snow-dusted vines to enjoy sweeping views of Keuka's distinctive Y-shaped shoreline.
After a leisurely morning, take a late-afternoon drive around Keuka's rim to visit Keuka Spring Vineyards for a guided tasting of their estate Pinot Noir and a behind-the-scenes look at barrel aging, then continue to Heron Hill Winery for a seated pairing of regional cheeses with their award-winning Rieslings while enjoying panoramic lake views from the tasting room. Finish the afternoon with a cozy stop at Ravines at Keuka (their Keuka tasting room) to sample small-batch experimental cuvées and hear about winter pruning techniques from the staff before returning to your lakeside lodging for sunset reflections.
As twilight deepens, enjoy a relaxed tasting and small-plate dinner at Bully Hill Vineyards where their storied tasting room and cozy fireplace create a welcoming atmosphere for sampling bold red blends and reserve Rieslings. After dinner, take a short drive to Keuka Lake State Park for a peaceful lakeside stroll beneath winter stars, then finish the night with craft cocktails and local dessert pairings at The Harford House to toast a day of scenic drives and memorable cellar conversations.
Ease into the day with a lakeside breakfast at The Boatyard Grill before driving north along Cayuga's eastern shore to Sheldrake Point Winery for a curated tasting of their estate Rieslings and a short vineyard walk to learn about cold-hardy varietals. Continue with a mid-morning appointment at Watkins Glen Harbor Hotel's nearby tasting room or pop into Taughannock Farms Market for a seasonal cheese-and-charcuterie pairing to enjoy while you take in panoramic views of the lake-perfect preparation for an afternoon of deeper culinary-and-wine explorations.
After a leisurely lakeside morning, drive south to Cayuga Ridge Estate Vineyard for a guided tasting of their estate Cabernet Franc and a cellar tour that explains cold-climate élevage; linger on their heated patio to take in lake views. Continue to Bellwether Hard Cider & Wine for a tasting flight that pairs small-batch ciders and hybrid wines with house-made sausages, then finish the afternoon with a convivial chef-driven pairing at The Grey Goat, where seasonal plates are matched to Finger Lakes varietals and you can compare notes from the morning's tastings before evening plans.
As dusk falls, settle into a riverside tasting at Union Springs Vineyards & Winery for a relaxed flight of estate Rieslings and a conversation with the cellar team about barrel aging before dinner. Follow that with a farm-to-table dinner at The LakeHouse on Cayuga where chef-driven seasonal plates are paired with local wines, then finish the night with nightcaps and live acoustic music at The Bluefrog Inn & Bistro for a warm, convivial end to a day of lakeside exploration.
Enjoy a slow lakeside start with breakfast and coffee at The Village Bakery & Cafe before a final tasting appointment at Hermann J. Wiemer Vineyard's tasting annex to revisit favorite Rieslings and pick up a bottle for the trip home. Before departing, take a short detour to Watkins Glen State Park for a brisk walk through the gorge (weather permitting) to stretch your legs and admire frozen waterfalls-an invigorating close to the Finger Lakes before the drive back to NYC.
After a leisurely checkout, drive toward the southern end of Seneca Lake for a relaxed late-afternoon visit to Bellangelo Winery, where you can enjoy a seated tasting of their sparkling and barrel-aged whites paired with artisanal chocolates in a warm tasting room. If time allows before the drive back to the city, stop at Finger Lakes Distilling for a quick tour and tasting of apple brandy and local liqueurs to bring distinct regional spirits home, then pick up one final bottle at The Gaffer District Wine Shop to round out your cellar notes before the journey to NYC.
Before your drive back to the city, enjoy a celebratory farewell dinner at The Harvest on the Lake, where a chef-curated Valentine's tasting menu showcases seasonal Finger Lakes produce paired with regional wines. After dinner, take one last lakeside stroll at Seneca Lake State Park Marina to breathe in the crisp night air and toast your trip with a bottle purchased earlier, then warm up with craft cocktails and live piano at The Seneca Harbor Station as a final, convivial send-off to the Finger Lakes.