This stage-set of a neighborhood remains the most expensive real estate in the borough—a house on the Promenade was recently listed at a record $20 million. The Promenade was once the saddest place in New York, with its grandstand view of the burning twin towers—and it hosted many a candlelight vigil—but that same panorama of the (truncated) Lower Manhattan skyline remains a great sight. From there, amble the streets and ogle the Federal, Italianate, and Greek Revival brownstones, atmospheric backdrop for the many writers—Walt Whitman, Truman Capote, Paul Bowles, and W.H. Auden—who have called this quarter home. A stop off at the Brooklyn Historical Society will put the surroundings in context (128 Pierrepont St.; 718-222-4111; www.brooklynhistory.org; closed Mon. and Tues.). Be sure to pick up a pocket-sized map at the front desk listing architectural highlights. Henry and Montague Streets are lined with restaurants and shops, though there's a surprising dearth of decent food here, considering the moneyed surroundings. Jack the Horse Tavern, a newly opened gastropub on the Heights' northern edge, is probably your best bet (66 Hicks St.; 718-852-5084; www.jackthehorse.com). At the southern end lies Brooklyn Borough Hall, a Greek Revival structure known as Brooklyn's oldest public building. Visit its farmer's market every Tuesday and Saturday year-round (as well as Thursdays from April to December). The New York Transit Museum hidden in plain sight on Schermerhorn Street below a sign that looks like an actual subway stop, is well worth your time—it has interactive exhibits and vintage train cars from all eras (corner of Boerum Pl. and Schermerhorn St.; 718-694-1600; www.mta.info/mta/museum).

Brooklyn may not have as many obvious tourist draws as its neighbor across the river, but its parties and festivals are not to be missed. If you can't get to Carnaval in Rio, the West Indian Carnival held each Labor Day is a boisterous, pulsating conga line of feathers, sequins, and steel drums blaring down Eastern Parkway (www.wiadca.org). The Mermaid Parade, held in Coney Island on the last Sunday of June, is the nation's largest arts parade, with thousands of revelers decked out in elaborate—and sometimes risqué—sea-inspired costumes. (Mermaids have a tendency to drift off into the ocean for a dip, which makes for quite the spectacle.) Celebrities such as David Byrne, Queen Latifah, and Moby have all sat in as parade royalty (www.coneyisland.com/mermaid.shtml). DUMBO Art Under the Bridge Festival is the biggest weekend in DUMBO, with interactive and guerilla-style art installations popping up all over the neighborhood (www.dumboartscenter.org/festival; last weekend in September). And Celebrate Brooklyn!, a summerlong outdoor festival at the Prospect Park Bandshell, boasts a dizzying spectrum of musical acts from indie stalwarts including TV On the Radio and Latin-punk superstars Manu Chao (www.briconline.org/celebrate).

Landscape architect Frederick Law Olmsted was reportedly more proud of this 585-acre idyll than anything else in his repertoire. He and partner Calvert Vaux secured the commission of Central Park several years prior but approached the design of Prospect Park, which was completed in 1868, with a vastly different vision. Think of it as a wilder, free-spirited version of its more famous cousin, with a lake for fishing, forested ravines, and horseback riding trails. Many formerly decaying landmarks have been restored, such as Lefferts Historic House, a quaint example of 18th-century farm life in Brooklyn, and the Beaux Arts boathouse, home to the country's first Audubon center. Overall, though, it's the grand sweep of the 90-acre Long Meadow that thrills, and where polyglot Brooklyn, with its lesbian softball leagues, Honduran soccer teams, and moneyed brownstoners all commingles in a hopeful, heartening display. There are multiple entrances, but the most convenient from Manhattan is via Grand Army Plaza, whose magisterial arch was built as a tribute to the victorious Union in the late 1800s.

Times have changed since Red Hook housed the city's longshoreman—the docks once depicted in the Mafioso flick On the Waterfront now greet the Queen Mary 2 when it cruises into town. Gentrification on Van Brunt Street is proceeding apace, and the happening strip is a good starting off point to get your bearings. Stop by Hope and Anchor for delish veggie omelets and Bloody Marys (347 Van Brunt St.; 718-237-0276; www.hopeandanchordiner.com). Baked is like an edgier Magnolia Bakery, with frosted Bundt cake, Wi-Fi, and a groovy interior by local firm Hivemindesign (359 Van Brunt St.; 718-222-0345; www.bakednyc.com). Red Hook Bait & Tackle has emerged as the neighborhood's de facto watering hole, with artists and old-timers downing Blue Point ale and playing darts (320 Van Brunt St.; 718-797-4892). A bit to the north lies Brooklyn Collective, a design coop featuring hand-dyed Milton Carter T-shirts and chunky gold-chain bracelets by Jess Yam (198 Columbia St.; 718-596-6231; www.brooklyncollective.com). Red Hook isn't accessible via subway—indeed, its remoteness is part of the appeal—but the New York Water Taxi runs a shuttle every hour on the weekends from Pier 11, on the corner of Wall Street and South Street in downtown Manhattan (nywatertaxi.com).