Union Square, Flatiron District & Gramercy

The bustling, throbbing, frenzied heart of this trio of neighborhoods is Union Square, where you'll find a mix of Hare Krishnas, skateboarders, streetwise chess champs and New Yorkers of all stripes meeting on the long rows of park benches to catch up over lunch. The triangular Flatiron Building and the verdant respite of Madison Square Park mark the boundary with Midtown just to the north. Gramercy Park, a romantic private oasis, offers a more subdued, stately residential area to roam.