Located in the heart of Long Island’s wine country, Southold is the perfect home base for exploring North Fork vineyards. Don’t miss One Woman Wines & Vineyards, which hosts “Tastings Under the Stars” with outdoor movies, bonfires, s’mores and a telescope to view the night sky every Saturday evening until Columbus Day.
While You’re in Town: Make a trip to Sparkling Pointe, Long Island’s top bubbly maker. The owners are frequent visitors to Brazil, and host an annual carnival at the winery, which will take place this year on July 23.
Where to Stay: The North Fork Table & Inn, which features an award-winning restaurant downstairs and four cozy rooms upstairs. Guests here will wake up to a complimentary continental breakfast; if you stick around for brunch at 11:30 p.m., be sure to order the house Bloody Mary, made with bacon-infused vodka. From $200 per night