Jamesport Vineyards
Your day of vino begins at this vineyard’s 19th-century tasting barn, which is just under two hours from the city. Drink your way through five tasting flights ($18 per person), and fortify for the afternoon with complimentary olives and cheese. (You’ll need it.) 1216 Main Rd, Jamesport (631-722-5256, jamesportwines.com). Parties of eight or more require a reservation.
Photograph: Courtesy Yelp/Vivid I.