Surfer bros and biddies will want to hop straight on the Jitney
or LIRR on a Friday afternoon to head out to Long Island’s
easternmost point. Known for its chill surfer vibes (despite
recently attracting swells of cool-kid crowds), beach bars and
gnarly waves, Montauk is a summer paradise for those in need of a
good break. Hit the water first thing Saturday morning and then
beat the crowds to Gurney’s or Surf Lodge for a
well-deserved bottle of rosé.

A favourite destination in upstate New York’s Adirondacks, Lake
George is your go-to for a long weekend break. Book a sprawling
lake house and spend days between the boat and the barbecue. If
your gang is of the sportier variety, rent some water skis or a
wakeboard and make the most of your waterfront location. Canoeing,
kayaking, hiking and cycling are also upstate must-dos, so pack
trainers in your weekend bag. When the sky is filled with stars at
night (a sure sign you’re far, far away from the city lights), set
up a bonfire and have an at-home summer camp night of s’mores and
scary stories.

Only an hour-long train journey from Penn Station, Princeton is
as doable for an impromptu day trip as it is for a Friday-to-Sunday
affair. If the sun and
rooftop crowds are just getting too unbearable, hop on the
train and head out to this preppy paradise. Start the day off with
a stroll around campus to check out the school’s gothic
architecture and eating clubs, then pop into sleek Mistral (a
favourite among students going to dinner with visiting family
members) for fresh burrata or salmon tartare and lavender
lemonade.

Leaving straight from East 35th Street at 4pm every day, the
Seastreak Ferry will have you on the shores of Martha’s Vineyard by
9:15pm the same evening. A mecca for all things
summer, this island greets you with beach houses and seafood
galore, most likely starting with a lobster dinner on the night you
arrive. En route to your weekend getaway, grab a few beers for the
boat and watch the city fade into the distance from the top
deck.

One of New Jersey’s most charming beach towns, Cape May is your
go-to for an all-American seaside escape. Rent a house or stay at
one of the adorable Victorian B&Bs by the water, and spend days
taking a cooling dip, flipping through books
and buying one ice cream after another from a beachside stand. Make
the most of the local seafood with dinners of oysters and wine or
clambakes on the beach.

For a laid-back alternative to the
Hamptons, Fire Island is the dream escape, offering both
proximity to the city and an abundance of beaches. A thin strip of
land running parallel to the south side of Long Island, it’s only
accessible by private boats or ferries leaving from Long Island.
There are hardly any cars here, so weekends here are spent
exploring on foot and cycling with a beach picnic packed into your
bike’s basket.