Coolest Places to Stay in New York, Borough by Borough

New York is gloriously contradictory. It will charge you silly money for a Midtown shoebox, then hand you a free ferry ride past the Statue of Liberty. I'm a former graphic designer who now chases the artsiest, most nightlife-forward corners of any city. Over the years I've learned that the cool move isn't the postcode with the famous name, it's the base that leaves budget for the night out. So here's where I'd actually sleep, borough by borough, with the sights, shows and seasonal bits that make each one worth it. Five picks, all judged on transit, free parking or free shuttles. Cool, obvs, but practical too.

Quick confession: I used to book whatever looked prettiest on the map, then winced at the total. Now I hunt for three things: a subway or ferry close by, free parking or a free shuttle, and a neighbourhood with its own pulse. Midtown is fine, but hotels there are convenient and often small and expensive, so I'd rather spend on the night out.

Tap a contactless card or phone on OMNY and after 12 paid trips in a week the rest ride free. No pass, no faff.

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Lower Manhattan is where I'd spend day one, mostly on foot. The Brooklyn Bridge is the rite of passage: go early, or around sunset on a weekday, because midday is wall-to-wall people. The 9/11 Memorial plaza is free and open daily, though the museum needs advance tickets. Over at the Seaport, DAYDREAM at the Balloon Museum fills the Tin Building with interactive installations by artists including Marina Abramović. The Banksy Museum on Canal Street scratches my designer itch for rebellious imagery.

Cross into Brooklyn Heights and the skyline does the heavy lifting for free. The Promenade gives you the classic harbour panorama, and below it Brooklyn Bridge Park runs down to DUMBO and Jane's Carousel. For the water, the Circle Line Statue of Liberty Super Express is a 50-minute round trip with live guides. It's my pick if you want Lady Liberty without giving up a whole island day.

Brooklyn is where my nights go. BrownstoneJAZZ is an intimate acoustic room in a restored Victorian brownstone in Bed-Stuy, with a Sunday after-brunch trio. It's 21+, tickets run about $54, and the house asks you to dress to impress, so leave the hoodie at home. Barclays Center hosts the Nets, and the Brooklyn Paramount books gigs most weeks. By day, Prospect Park is free to wander, the Botanic Garden's cherry blossoms light up spring, and the Brooklyn Museum on Eastern Parkway makes a full afternoon.

Grand Army Plaza, with its triumphal arch and a Saturday greenmarket, is the gateway to Prospect Park. A simple, functional base is exactly what lets me splurge on the gig instead of the room, and this side of Brooklyn suits that.

Queens is where I find the best food-per-dollar in the five boroughs. Flushing Meadows-Corona Park holds the Unisphere, the Queens Museum with its room-sized panorama of the city, Citi Field, and the US Open each late summer. Governors Ball takes over the park in early June. Ride the 7 train to Flushing's Main Street, one of the largest Chinatowns in North America, for dumpling shops and food courts. Listings currently include Cirque Kalabanté at Queens College. MoMA PS1 is a short ride away for contemporary art and summer courtyard dance parties.

LaGuardia has no rail link, but the Q70 LaGuardia Link bus is fare-free and runs to Jackson Heights and Woodside, where the subway and LIRR connect. That makes Queens a smart, cheap launch pad for the whole city, and for the food crawl.

Staten Island is the loophole nobody mentions. The ferry is free, runs 24 hours and takes about 25 minutes across the harbour, passing close to the Statue of Liberty. Take the right-hand side going out, and ignore anyone selling tickets. The Greenbelt has about 45 km of woodland trails, Snug Harbor has gardens and arts groups, and the New York City Marathon starts here on the Verrazzano-Narrows Bridge. Driving? Congestion pricing hits Manhattan at or below 60th Street, so free parking out here is a quiet win.

Snug Harbor's 83-acre campus of Greek Revival buildings, the Staten Island Museum and Historic Richmond Town show the island's slower side. The Staten Island Railway runs from St. George along the island's spine. It's low-key, honestly a bit sleepy after dark, and that's the trade for the savings. The ferry never sleeps, though, so a late Manhattan night still gets you home.

• Halloween night: the Village Halloween Parade on Sixth Avenue at 7 p.m. Free to watch, and anyone in costume can march.
• Late October: Bryant Park's Winter Village opens with a free-admission rink.
• Early November: the Radio City Christmas Spectacular starts, then the NYBG Holiday Train Show in mid-November.
• Thanksgiving morning: Macy's parade, its 100th march. The Rockefeller Center tree lights up the Wednesday after.
• Last Sunday of June: the NYC Pride March down Fifth Avenue to Stonewall. Fire Island's Cherry Grove and the Pines are the classic LGBTQ+ summer escapes.

If I could book just one, it'd be the Marriott by the Brooklyn Bridge. It's the easiest to do on foot, and the subway is practically outside. But if you're a food obsessive, the Flushing Westin is the secret weapon. I'd eat my way down Main Street any day. Prices and availability can change, so confirm when booking.

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