8 Ave, Chelsea

Not as historic or as pretty as the West Village, not as lively as Chelsea, West 15th Street is a largely commercial area with little distinctive character or charm. It has its perks - it's close to several 14th Street/Union Square subway stops for a variety of subway lines - and the convenience of Union Square, with its myriad cafes, bookstores, and record shops (not to mention a pleasant picnicking park). But West 15th Street itself is little more than a basic shopping destination. Nearby high-street options include Pier 1 Imports, Foot Locker, Urban Outfitters, and Staples, while dining choices tend to be of the equally chain variety: there's a Subway, and a nearby Starbucks. Further west, however, choices get more interesting - visit the Chelsea Market for some local finds, or try trendier dining options like Le Gamin Cafe, La Taza Deora, or the Chelsea-fied Vynl. Avoid the Port Authority building at night - it's a bit sketchy.

Chelsea definitely is not a historical place. Most of the buildings have been redone and there are virtually no brownstones in the neighborhood. Furthermore, I don't know why this area is so popular considering there are no good restaurants or bars and the streets are always packed. But there are a few things worth looking at on this street on your way to somewhere else.
There's a really cool building on the corner of 26th and 12th called the Starrett-Lehigh Building. It is all windows at quite tall. There are a number of fancy businesses in this building including the headquarters for Martha Stewart Living. The windows are pretty impressive, I must say. Of all the many art galleries in Chelsea, the block of 26th between 10th and 11th is probably the best strip of them. Or, at least they make up some of the most famous. If you're into art by people whom are mostly still alive, do this block.
The corner of 26th and 8th houses the Upright Citizen's Brigade theatre. This is one of the most famous improv theatres in the world and they really do have some great shows. There's one in particular called ASSSS cat on Sunday nights that always sells out ahead time but anyone who lives in NYC has to go to this show. The performers are incredible and there are often guests from SNL and 30 rock in the lineup.
There's not a lot to do in the way of bars and restaurants on this street. In fact, we always have to make quite a hike to go for drinks after a UCB show. And, even within blocks, the options are pretty bleak. But, there are a number of schools on this street including FIT, a dance school and UCB. There are also a number of bizarre stores (like sewing shops) on this street but I don't know that I'd go out of my way for any of them unless I needed something very specific. There's one cool historical thing on the street and it's called Writers' House. It is a quite successful publishing house that is in the literal house of the Astors before they became ridiculously weatlhy. It's very old and very cute and I think the fact that it's a publishing business now sort of commemorates the old school writing vibe that the west side once possesssed.

The point at which the grid system starts to get complicated, West 14th Street stands between midtown proper and the West Village, incorporating elements of both neighborhoods. On the one hand, West 14th Street is near a number of attractive Village locations - from Greenwich Avenue's neo-quaint tea house Tea and Sympathy to the taverns and bars dotting trendy Jane Street - on the other hand, the street itself is more likely to play home to discount big-box retailers and Century 21s than it is to host arty boutiques selling handmade crafts. This is convenient for the frequent shopper, of course, but what it gains in convenience it loses in charm. West 14th Street is very much a commercial location: you can find anything from clothing to electronics here, and get around quite easily due to the high transport links. It's not, however, an extraordinarily livable area. If you're looking for charm and comfort, head further south and further west,