Prince St, SoHo

NoLita was trendy once. A tangle of streets located just to the north of tourist-magnet Little Italy, NoLita was a hidden gem of a neighborhood - filled with minimalist-designed loft buildings, artsy coffeehouses, and bars where those "in the know" drank until morning. Today, however, NoLita has lost a bit of its charm. It's no longer New York's next big thing, but it doesn't have the same depressing has-been feel of the Meatpacking District. Somehow, between gentrification and the shame of becoming outre, NoLita has become rather nice. It has a distinctively "downtown" feel (think SoHo or Tribeca rather than the West or East Village - not bohemian but nevertheless artsy and sophisticated). Prince Street in particular isn't known for much (beyond being the home of Rupert Murdoch), but it's a great place to live nonetheless. There's an enormous cluster of inexpensive, interesting restaurants, especially around LaFayette Street (try Cafe Fallai, or the Savoy Restaurant if you're feeling luxurious), and the nightlife scene has managed to outlast its trendiness, combining New York elegance with a more laid-back vibe. If this area is a has-been, we're happy to be out of style!

There's a townhouse on the corner of Prince and 6th Ave that is restored to it's original granduer (it was built in 1834) and it's such a cool thing to take a peek at. Raoul's is an amazing restaurant on Prince at Thompson. The food is divine, it's small and cozy, and the owner is a riot. This restaurant is a must. And, on the complete opposite end of the spectrum, Milady's is a total dive bar at Thompson that is also amazing. It's so sketchy and awful and awesome.
Once you get past West Broadway, you're headed into major Soho / Shopping / Tourist. Prince is lined with shop after shop after shop. It's dizzying, but the street has almost anything you can think of. . . and, a sea of people.
The corner of Prince and Lafayette is where President Monroe died (just 5 days after Jefferson and Madison). He was in his daughter's house which is still there. Old St Patrick's Cathedral is on the corner of Mott and Prince. It was the first Catholic Church erected in NYC and it is really beautiful. And, just across Mott is the actual, original Ray's Pizza. So, if you're gonna do Rays, this has to be the one you do.
Cafe Habana is on the corner of Mott and Elizabeth. This was the first dinner I ever had in New York and every time people come to visit me, I take them here. It is tiny, the food is delicious and it's exactly how you would imagine a New York place to be. The wait is always insane, though, so be warned.
Prince is such a pretty street that it sucks that it's so painful to get around -- especially on weekends. But, there are a number of places that make enduring the crowd more than worth it.