This article is part of a guide to New York from FT Globetrotter

When I first moved to New York for a work stint a decade ago, the Upper East Side was the last place I wanted to live. Back then, I presumed that districts such as the Village, the Lower East Side or Hell’s Kitchen were achingly cool, while Brooklyn was hipster(ish) and the Upper West Side was intellectual.

But the UES — to cite its ugly moniker — seemed stuffy and boring, without a ripped jean or wild bar in sight.

Wrong. In 2014, I moved to Manhattan for a second stint and stumbled on a great rental deal in a corner of UES known as Yorkville, close to Gracie Mansion, the official residence of the mayor of New York City.

I moved there temporarily, planning to relocate somewhere cooler as soon as I could. But six years later I am still there, having realised belatedly that the neighbourhood is convenient, relatively tranquil, and blessed by river views and a great park — and some delightful spots to eat and drink.

No, these places are not hip or wild — though Second Avenue has so many students that it does get rowdy — but there are memorable experiences to be found. Here are five of the best.

If you thought a speakeasy was something you only saw in films about America’s prohibition era, think again. Tucked away at the back of a tiny ice-cream parlour — the UES on Second Avenue — is this jewel of a bar that bills itself as a “speakeasy” because it is unmarked and you have to give a password to enter through a secret door.

Once through, you descend into a cosy joint with great cocktails and a bohemian atmosphere. Try the excellent ice cream from SoCo Creamery at the bar (I love the salted caramel). If you get truly hungry, go before or after to the atmospheric Writing Room restaurant next door, or Café d’Alsace across the street.

The diner is the ultimate American cliché — and The Mansion on the corner of 86th and York Avenue is a must if you want to get a sense of Yorkville. Nobody goes here for haute cuisine or trendy health food: think pancakes, French toast and bagels for breakfast, chicken soup or spinach pie for lunch.

The Mansion is the perfect place to soak up the Manhattan atmosphere or for people-watching, since it is open (almost) all hours and celebrates all the American festivals (Halloween, Christmas, Hannukah . . .) you can imagine.

Go at dawn to see off-duty police and families with small kids, or at lunch to see local pensioners eating the delicious chicken soup together, or on a weekend evening to dine among hordes of local teenagers drinking milkshakes.

Sushi of Gari is not a place to go to for stylish surroundings: the restaurant is small, with odd lighting. But the sushi is excellent, served by authentic Japanese sushi chefs. And the restaurant attracts well-heeled locals and the odd celebrity.

The Mark hotel technically is not in Yorkville, and admittedly it fits the stereotype of the UES: expensive, swanky and a bit stuffy, with wood panelling.

But I have included it since it is also my favourite place for a smart brunch or supper: the food is excellent, the tables are spaced far enough apart to feel private, and if you sit in the atrium there is a lovely airy feel (better still, get a table on the small outdoor patio).

The avocado toast, Caesar salad, black truffle and fontina cheese pizza and the hamburgers are among my favourites. The bar next door is also a stylish place for a cocktail.

If you want an offbeat experience on a sunny weekend afternoon or evening, take a picnic to the southern shore of Randall’s Island. Most UES residents only know about this place through sports: with more than 60 sports fields, it is the main venue for training and matches for Manhattan children.

But if you head here on a summer weekend, you will also find hordes of families from Harlem, just across the river, who stage picnics on the grassy river bank or use the public barbecues to cook.

The air is full of aromatic barbecue smells, Spanish chatter, vibrant music and the shriek of kids, all set against stunning views of the city.

To get there, walk for 10 mins up the river path from Gracie Mansion (88th and York), then cross the river over the green footbridge (Ward’s Island Bridge) and turn right to the south shore.

Lastly, for another authentic flavour of Yorkville go to Schaller & Weber on Second Avenue, an old-style German delicatessen and butcher. This is one of the last vestiges of this neighbourhood’s ethnic past (Yorkville used to be known as Germantown because so many German immigrants settled here in the 19th and early 20th centuries).

Head to Schaller’s Stube, the kiosk next door, for excellent sausages that beat an American street hot dog hands down.

What are your favourite places to eat and drink uptown? Tell us in the comments

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