We really have no idea; after all, there are lots of streets in the world, and no one can know them all intimately. But, in our experience, here are some candidates from the US. (Note: Please don’t ruin these areas; if you’re a typical fat American tourist wearing shorts, sneakers, and a tee shirt, go somewhere else. Most of the rest of America is designed just for you. And these areas are for adults; you can take your whiny kids to Disneyland.)

Abbott-Kinney Blvd in Venice, California– Very Cool and Laid Back
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When people think of Venice California, they think of the grungy but fun boardwalk area along the beach, where you can do a walk in to a doctor’s office for a medical marijuana “prescription”, buy a million tee shirts, check out the bodybuilders, or just watch the waves of unwashed people pass by.

What’s truly amazing is that just a few blocks away from the beach is a totally different scene; laid back, very hip, and buzzing with creative endeavors; Abbott Kinney Blvd. A few years ago, I actually bought a wonderful oil painting from a local artist who was working in a semi-abandoned building with other artists – which happened to be directly next door to actor Robert Downey’s mansion, which happens to be a few doors down from the local Intelligentsia coffee outpost, which was closed on one my visits as they shot a scene for a TV show there – which is so LA.

Some of the best restaurants in the LA area are located on AK, as well as various food trucks, cool clothing stores, and a few art galleries. You can’t have a cool area without cool people, and in large part this area is what it is because so many of the locals are creative – this is the kind of neighborhood where a contractor might be a painter in his off hours. You may not even think you’re in America; my first time on AK I noticed something was strangely missing, then I figured it out - the absence of fat people.

You’ll see lots of the young and hip here, many wearing the somewhat clichéd hipster hat. You can stroll all of AK easily in one visit. You won’t find bargains here; the best jeans are $400, but you will find reasonably priced places to eat and drink. It’s a very long but doable walk from Santa Monica; parking is possible but challenging. Best option if you’re staying in Santa Monica; bike. Like all shopping areas, AK is most crowed on weekends, but usually congestion free.

Lower East Side Manhattan, New York City – Prince and Orchard Streets – Hipster Heaven
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These may well be the coolest streets in America, at least at the moment. They are filled with an amazing assortment of small intriguing restaurants and bars; hipster heaven. They also have that somewhat indescribable New York vibe, a little dark. At night these areas are magical, as they stay alive with locals, and the hole in the wall restaurants are lit by candles or hanging lamps. If you’re visiting, the Blue Moon hotel at 100 Orchard has large rooms, and a very non-cookie cutter vibe. Prices will be most expensive in the fall, when there is spillover from the nearby, but totally different, Wall Street district. Blue Moon is directly across the street from the Tenement Museum.

What makes Orchard and Prince Streets are the small, intimate spaces; whether it’s a restaurant or a shop, just about everything on these streets is at a very small scale, which means they’re not generally big enough to cater to the chains. You’ll find locally owned coffee shops instead of Starbucks. The area has drawn a huge number of entrepreneurs willing to use their creativity to run small restaurants or bars or clothing stores that will never become the next Gap, or Cheesecake Factory. If these people ever wrote a business plan (unlikely) it basically said, let’s do something really cool where our friends will come over. Every kind of food, coffee, cocktail, dessert is available on these streets, which are within walking distance of the touristy and overrun Soho.

On Orchard Street, you can walk right by a typical basement Chinese joint that looks just like thousands of other semi-run down Chinese joints – until you realize it is Mission, one of the hottest restaurants in New York, and a pioneer in unique Chinese food. But that’s very Orchard Street – you have to know what you’re looking for, or just be willing to experiment. Prince Street empties out a bit as you move away from bustling Soho; Orchard will rarely be overrun, unless there is a tour group standing in front of the Tenement Museum.