To me, New York feels like cities within a city. Its endless maze of cross-stitched streets is a network of paths and lives powered by an energy that never naps, and an airborne excitement that anticipates discovery. Everything and anything feels possible in New York. When we plotted our trip we planned as if we would see every sunrise and every sunset.

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Williamsburg, Brooklyn

Williamsburg is the perfect starting point, not because it was our first stop, but because whenever anyone asks me about New York I blurt out, “We loved Brooklyn!” But we really did, we loved Brooklyn! After a hefty dose of Manhattan mayhem, a large Java Chip Frappuccino topped with whipped cream (when in Rome), and a sweaty ride on the L-train we arrived in Williamsburg. (New York’s subway is gloriously warm in winter and stupidly hot in summer.)

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In comparison to Manhattan, Williamsburg felt ghostly and intriguing. Rewind a decade and you would find it predominately populated by the Hassidic Jews, first generation Italians, and Puerto Rican immigrants. But, much like the East Village 30 years ago, gentrification is setting in and Williamsburg is becoming the neighbourhood of creatives – home to the artist, the maker, the musician, and the inventor. The industrial landscape has been personalised by idiosyncratic restaurants and bars, with cluttered thrift stores and artisan boutiques scattered in between. Lofts have been renovated and attached homes have been converted into gorgeous spaces.

Williamsburg’s creativity made me curious – I peaked into every coffee shop, and pressed my nose against many a store window, intrigued by the innovation and design. After a long and inspirational walk down Bedford Avenue and its side streets we stopped at a little corner restaurant called Allswell for lunch. It felt like an old countryside inn, one you would find in the middle of Sherwood Forest (minus the swatches of quirky, mismatched calico wallpaper and chandelier, of course). The burgers were hearty and the service was personable. Allswell is the kind of place that would feel like home, if we stayed a little longer.

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From Allswell, we made a beeline to OldFellows for a scoop of their best. OldFellows’ ice cream is made from scratch and with every serving they donate $0.05 to the Food Bank for New York City. Our attempts to eat dessert overlooking the water ended in sticky hands, and what felt like an inhaling of cherry gelato, instead of a savoring.

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Chelsea Market & the High Line

Chelsea Market may be a bit touristy, but not cheap and spoiled touristy. I mean who doesn’t love an enclosed urban food hall? After 15 years of feeding, the market has grown a reputation of being one of the best in the world. There are plenty of pleasant things to taste and wares to touch and admire. An offshoot of Brooklyn’s Artists and Fleas has moved into Chelsea Market with some of New York’s best designers and makers filling the space. When we grew tired of starring at the delectable produce, which would sadly never make it into our pantry, we browsed through Anthropologie and I found jeans at Free People’s popup sample sale. (Bonus!)

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We exited Chelsea Market near 16th Street just below the High Line – New York’s first public garden in the sky. These kind of urban projects make my heart sing. The High Line was built on a historic, raised freight rail line between Gansevoort Street in the Meatpacking District and West 34th Street, between 10 and 12th Avenue. It is now a boardwalk in the sky, running through a narrow park inspired by the self-seeded landscape that sprung up during the 25 years when the train was not operational. Encroaching buildings and city views juxtapose the textured grasses, trees and shrubs. This is perfect place to stroll in the early morning with a cup from Blue Bottle Coffee, or on a summer’s evening with a scoop from Italian L’arte del Gelato. (Both conveniently located on the High Line at West 15th Street.)

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Barnacles and mussels

The Frying Pan – without a doubt the catch of the day! This historic lightship spent three years at the bottom of Chesapeake Bay (and it has the barnacles to prove it), but was salvaged, docked on a railway car barge, and converted into Pier 66 Maritime Bar and Grill. We ate mussels, sipped on fresh coconuts and drank cocktails from the top of vessel, while we waited for the sun to set. Could it get any better?

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Underground jazz in the East Village and the oldest bar in New York

Kris’ aunt and uncle have lived in New York for over 25 years, but are still exploring and unearthing secret spaces. They took us to a local jazz club in the East Village (one which can’t be named). From the outside, nothing would suggest that it was any kind of gathering point… except for a tiny sticker on the door. The club was so packed that Kris and I had to sit on cushions with a worms-eye-view of the guitar player who towered above us. It was an incredible experience, not because the music was amazing, or because the double base player’s fingernail nearly landed in my lap, but because it was local and different. We felt like authentic New Yorkers.

New York’s oldest and finest

After a pint at Zum Schneider, the East Village’s first German beer hall, we pub hopped to McSorley’s Old Ale Tavern – the oldest standing pub in New York. Walking into McSorley’s is like taking a glimpse into old New York. Ancient artwork and old article clippings line the walls, sawdust covers the floors, cobwebs hang from the ceiling, and best of all McSorley’s pours like no other pub. Abraham Lincoln is said to have stopped at McSorley’s for a drink, to calm his nerves, after his famous Gettysburg Address. E.E. Cummings called McSorley’s “snug and evil” and described their ale as one which “never lets you grow old” in his poem “i was sitting in mcsorley’s”.

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There is so much more play to have in the “world’s biggest urban playground” but these places and spaces were some of our most memorable, and perhaps will become yours when you next visit New York City.

Some of our other summer favourites

• Go to a Yankees Game

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• Watch free summer concerts at the universities and in the parks

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Lisa Fischer is an incredible singer and songwriter – she has been touring with the Rolling Stones since 1989

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• Open a book at the New York Public Library’s outside reading area, while listening a piano player tinkle at lunchtime

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• Spend an afternoon writing in the library’s exquisite Rose Main Reading Room

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• Enjoy gourmet, 3-course $25 lunches and $38 dinners at nearly 300 participating NYC Restaurant Week restaurants

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• Stroll around Central Park, watch the buskers, enjoy the sunshine, feed the squirrels and have a nap under a tree

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• Take the tram to Roosevelt Island at night

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