“Nothing has happened to me yet. That’s why I’m going to New
York!” Sally utters to Harry as they commence their
road trip. New York plays a blinder in this Nora Ephron
classic, so if Washington Square Park (where it all begins) is too
obvious a destination, perhaps the film’s restaurant offering will
pique your interest. Head to Café Luxembourg on the Upper
West Side, where Harry and Sally try to set each other up with
their best friends. Sally ordered grilled radicchio but we’d
recommend the swordfish at this relaxed neighbourhood spot.
Alternatively, head to Katz’s Deli for “whatever she’s
having”. At Katz’s, Harry and Sally debate whether women fake
orgasms – and Sally promptly proves that they do by faking one in
the middle of a crowded bistro. At this 125-year-old deli the line
in (to order) and out (to pay) are both snaking, especially at the
weekends, so it’s best to expedite your lunch by sitting at a
served table.

Bloomingdale’s, the home of the meet-cute, where Jonathan Trager
(John Cusack) and Sara Thomas (Kate Beckinsale) meet while shopping
for glove. Despite being there to buy last-minute gifts for their
respective lovers, the scene swiftly turns to romance. Cut to the
eponymous Serendipity III, a popular restaurant in the
Upper East Side known for its trademark frozen hot chocolate –
Sara’s favourite place in the city for a sweet treat. While most
Manhattanites above the age of 11 would probably rather go without
than grab dessert here, the novelty factor is undeniable – it may
be predictable but it’s also delicious. Douse yourself in the overt
cliche that is a walk in Central Park and follow the walkway
leading to the gilded Bethesda Terrace for a sneaky canoodle.

If there’s one thing you take away from You’ve Got Mail (aside
from the promising power of adult pen pals) it’s their throve of
top-notch food spots. Among other businesses patronised by both
Kathleen (Meg Ryan) and Joe (Tom Hanks) is legendary West Side deli
Zabar’s. When Kathleen finds herself in the cash-only
line Joe swoops into the rescue (chivalry is alive and kicking).
Later across town, Kathleen waits for NY152 (Joe’s mailbox name) at
Cafe Lalo. And waits and waits. Joe Fox shows up and orders a
“mochaccino decaf, non-fat” (you can order the same) and waits a
while with an unknowing Kathleen. Cafe Lalo main draw is the
display cases bulging with an assortment of cakes, cookies and
pies, but despite its distinctly American desserts it’s the coffee
shop’s attempt at European suave – think art-nouveau posters and
French windows – that give it its romantic flair. Not a coffee fan
(and so presumably not a New Yorker) grab a hot dog at NYC mainstay
Gray’s Papaya a la Kathleen and Joe. If you’re a cheap
date, perhaps you’ll even be impressed by a $1.25 meal –
regardless, these dogs are some of the tastiest in the city.

“He adored New York City, he idolised it out of all proportion…
New York was his town, and it always would be.” The opening line in
Manhattan
reminisces on the New York of Woody Allen’s childhood. Follow suit
and start things off with a trip to Sutton Place Park to look out
at Queensboro Bridge just like Isaac and Mary. After a suitable
amount of gawping, head to the Boating Lake at Central Park. Go to
Bethesda Fountain (yes, again) and head north to retraces Woody’s
cinematic steps. After a morning of ambling through parkland, head
back to Zabar’s for smoked fish, bagels and knishes.

Debonair types will relish the swanky surroundings of the
21
Club members’ bar. Pass its distinctive jockey-topped railings
and stop off for olive-garnished drinks in an ode to Michelle
Pfeiffer. Her character, Melanie Parker, has cocktails in the
lounge here before skipping out to take her child to a soccer game
(George Clooney in tow). For something a little more
budget-friendly (if touristy as anything) make tracks for Pier 83
and hop aboard the Circle Line Ferry. Camera-weilding
crowds aside, there’s something comfortingly retro about this date
suggestion. Once you’ve docked, head for the Highline (only
completed in 2014 and therefore not in the film) and amble down to
the Meat Packing District to re-ground yourself in 2019.