Morning
Downtown Brooklyn, bordered by the neighborhoods of Brooklyn Heights, Boerum Hill and Fort Greene, is one of the borough’s hubs of arts and culture. BAM (Brooklyn Academy of Music), for instance, is a performing arts center that showcases a range of offerings—theater, film, opera and more, much of it with an avant-garde bent. In warmer weather, the outdoor space MetroTech Commons holds exhibits, performances and other special events. BRIC House and the New York Transit Museum are among some of the other cultural institutions in the area. Of course, the neighborhood is also home to a range of restaurants—from small bistros like Café Luluc to classic diners like Junior's, whose cheesecake is the stuff of legend.
Afternoon
Farther north, located on the East River, DUMBO is home to art studios, galleries, luxury boutiques and independent bookstores. (The name is an acronym for “Down Under the Manhattan Bridge Overpass.”) The neighborhood's recently developed Brooklyn Bridge Parkprovides spectacular views of the Lower Manhattan skyline, and is a wonderful location to unwind and take the kids for a spin on Jane's Carousel. Stop for a comfort-food brunch at Vinegar Hill House (weekends only; otherwise, it opens at dinnertime), or join the line of hungry diners for crispy coal-oven pizza at the famous Grimladi's. Cap off your meal with homemade frozen treats at the charming Brooklyn Ice Cream Factory.
Evening
Enjoy a stroll on the Brooklyn Heights Promenade, part of Brooklyn's first Historic Preservation District. Measuring about a third of a mile, the esplanade offers scenic riverfront views and the neighboring streets are lined with gorgeous town houses and mansions. (It also served as a backdrop for movies like Annie Hall and Moonstruck.) Near stately Brooklyn Heights are Boerum Hill, Cobble Hill and Carroll Gardens, providing more territory to explore. Local dinner and drinking options include French bistro Bar Tabac and Southern barbecue joint Char No. 4.
If you'd rather call it a night in Manhattan, head to The Dead Rabbit Grocery and Grog in the Financial District. This Irish whiskey bar has won numerous awards, including North America's Best Bar of 2014 and Time Out New York's best new cocktail bar of 2014. You can get there by traversing one of the City's most famous attractions—the Brooklyn Bridge. Walking the 130-year-old structure, and taking advantage of the photo ops along the way, is a must for many visitors. (Bonus points if you snap pictures during sunset.)
Next: Day Four—SoHo, NoHo, East Village, Greenwich Village & West Village