The tasting room with a fire going. The bookstore that doesn't mind if you stay two hours. The museum nobody on TripAdvisor mentions. Rain on a lake is one of the better problems to have.
Naples's founding winery — 1888, still standing on the same Widmer Hill site above the village. Tours walk the old barrel rooms and the roof-aging sherry solera, which is one of the few in the country. The tasting flight leans sweet and heritage-style; go for the history first and the wines second.
Bristol Springs stop for grape products beyond wine — the Concord-grape mustard, the wine sauce, and a tasting room that lets you sample everything. The retail store is the actual reason to stop; the wines are entry-level sweet-side. Line up gifts and pantry goods for the drive home in one visit.
The old New York Wine & Culinary Center, rebranded and still doing the same work — a full restaurant, tasting room, and hands-on cooking classes built around New York State producers. Book the chef's-counter seats if you're eating; sit at the bar if you're pouring. Walkable from Kershaw Park and the City Pier.
The 50-acre Victorian estate on the north side of town — nine themed gardens, a 40-room mansion, and the reason to spend a rainy afternoon in Canandaigua. Peak bloom hits late June through July. The Japanese garden and the Italian garden are the two you don't skip. Buy the timed entry for the mansion tour.
The 1816 Federal-style home of Gideon Granger, U.S. Postmaster General under Jefferson, with the largest horse-drawn carriage collection in the region out back. Guided tours only; check the day's schedule. The rainy-afternoon move in Canandaigua when you've already done Sonnenberg. Runs Tuesday through Saturday in season.