This post was originally produced as an assignment for the MatadorU Travel Writing program.

Fifteen years ago, the Los Angeles beach community of Venice was the stomping ground of bohemians and gangsters, with pockets so crime-ridden even the pizza man stayed away. Today, GQ calls its hipper-by-the-second thoroughfare, Abbot Kinney, “the coolest block in America,” and money pouring in from high-tech companies like Google has sparked the new moniker “Silicon Beach.”

How to make sense of a place where the rough and tumble rubs shoulders with the shiny and new? Below, a guide to enjoying both sides of the Venice dichotomy.

Old-school coffee: The Cow’s End Cafe

Marching to its own beat since 1989, this two-story barn features life-sized plaster cows, a patio of regulars debating the city’s best fish taco, and a soundtrack of Dj Shadow and Boards of Canada that’s like a warm blanket from 1999.

New-wave coffee: Intelligentsia

Locals line up here in skinny-legged droves for responsibly developed brew. Will suit coffee snobs, those who enjoy paying $10 for a chocolate bar, and you with the handlebar mustache riding past on your fixie!

Old-school hub: The boardwalk

Muscle Beach, novelty t-shirts, disco-dancing rollerbladers, and the basketball courts from White Men Can’t Jump. It’s the kind of place where anything can happen, but this much is guaranteed: “Nurses” in green jumpsuits will try to sell you weed. World-class skateboarders will perform sunset aerials. And a man in pineapple sunglasses singing, “Jingle bells jingle bells, help me get drunk,” will expect your change.

New-wave hub: Abbot Kinney Blvd

A beacon of cool, Abbot Kinney is a seven-block stretch of boutiques, galleries, cafes, bars, and gourmet food trucks. Find everything from locally crocheted swimwear (at Undrest), to artful floral arrangements (at Fiore), to a sea of wayfarers to go with your foraged mushroom pizza (at “it” restaurant Gjelina).

Old-school sightseeing: The Venice Canals

Storybook bridges arching over tranquil waterways flanked by rows of impeccably maintained homes, this six-channel enclave is all that remains of the once 16-mile network covering Venice before the popularity of the automobile and disappearance of the council treasury (along with treasurer Mr. James Peasgood), forced the city to fill them in 1929.

New-wave sightseeing: Venice Garden and Home Tour

The tour may not be new (it celebrates its 20th anniversary next year), but the homes featured represent some of the most cutting-edge design around. Think light-flooded lounges with wrap-around sliding doors and bamboo-shaded rock gardens with Moroccan lanterns and fire pits.

Old-school art fix: Graffiti + murals

The cafes and alleyways of Venice are just blank canvases for the neighborhood’s street artists, who paint the town with everything from Japanese-inspired pop art to portraits of icons to nostalgic scenes of the glamorous past.

New-wave art fix: Venice Art Crawl

On the third Thursday of every month, bars, bookshops, and even private residences become pop-up galleries with shows highlighting whimsical avocado paintings by Jehan Valiente and “yarnbombing” (aka trees in sweaters) by Arzu Arda Kosar.

Old-school booze: Del Monte Speakeasy

According to lore, the Del Monte (née 1915) is LA’s oldest bar, surviving Prohibition as an illegal booze distribution center that kept Angelenos in smuggled liquor via a network of underground tunnels. Today, it’s the neighborhood’s best option for live entertainment, featuring a comedy and burlesque night (Wednesdays, free) and performances by Raphael Sadiq and Feist.

New-wave booze: The Other Room

Exposed brick, candlelight, rotating art, and enough beer and wine options for three floor-to-ceiling chalkboards. On warm Sundays, the tall street-side windows fling open, turning nearby tables into a beer garden.

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