A Guide to Visiting New York for the Second Time

New York is one of those cities you can’t just do once. It transforms at the speed of lightning, meaning the list of things to do in New York is not just long, but ever changing. I've been lucky enough to visit the city four times now, and each time it has seen me enjoy a completely new experience, from warm summer nights in Greenwich Village, to walks through snow-covered Central Park.

Even in a blizzard, which serendipitously occurred during my most recent visit, New York was still full of possibilities, most of which existed beyond the classic Midtown town haunts. You just need to know where to go. Below I've listed the classic first-time haunts followed by their more unique alternatives. Ideal for a second, third or even fourth time visit.

If it’s your first time in New York, you'll want to stay in Time Square. It’s bright and busy and where all of the action takes place. Once you’ve stayed there though, you’ll know not to stay there again. Time Square is fun and a central location, but it’s not the real New York, much like how Piccadilly Circus doesn’t really represent the real London.

If it’s your second visit, you're best off branching out from a mid-town location and opting to stay in one of the boroughs such as the Upper East Side, Upper West Side, Greenwich Village or even Brooklyn. Staying in these areas will give you a glimpse of local life in New York and help you discover gems that only the locals know about.

WE RECOMMEND: For a stylish stay with a residential feel, I love The Surrey on the Upper East Side. Beautifully positioned between Madison Avenue and Central Park, this five-star hotel features a guests-only rooftop bar, an impressive art collection and an on-site Michelin star restaurant, Café Boulud, which is beloved by both guests and locals. Also, don’t miss the delicious Madeleines, baked fresh every day and dangerously addictive. Book your stay at The Surrey in New York.

Sprawling for 843 acres from 59th Street to 110th Street, there’s no avoiding Central Park in New York. And nor should you. The Park is a superbly planned green space featuring everything from meadows, a zoo and a tennis centre, to an outdoor theatre, a few lakes and even a castle.

It may be the largest in the city by a mile, but it’s certainly not the only outdoor spot worth your time. Madison Square Park enjoys a beautiful view of the Flatiron Building while Washington Square Park is a great place for people-watching. One stretch of city green that’s quickly gaining in popularity is the High Line. Once an abandoned elevated rail line, the space has been converted into a green walkway, complete with public art and great views of the city.

HOW TO DO IT: Start the High Line at any of the entry points to the West: Gansevoort Street, West 14th, 18th, 20th, 23rd, 26th, 28th, 30th or 34th. There are disabled access points at West 14th, 18th, 23rd, 30th and 34th. Walking the 1.45-mile route is completely free and is best enjoyed on a sunny day.

As the quintessential New York City building, the Empire State has long been the go-to for getting a bird’s eye view of the city. Dating back to the 1930s, complete with Art Deco lobby, the building still boasts the highest open-air observatory on the 86th floor, made iconic in that tear-jerking scene from Sleepless in Seattle. You can even travel up to the 102nd floor, which can be reached by a manually operated Otis elevator.

Once you’ve got a taste for heights though, you’ll find the highest view of New York at the top of the One World Trade Center. Located Downtown, the One World Trade Center stands 541m tall, with an observatory located on the 100th floor. The lift in itself is an experience, featuring a complete 360-degree, 3D video of the changing New York skyline. The ride in the Sky Pod Elevator to the top takes only 47 seconds and I can testify, you can hardly feel you're moving! Once there the view is revealed (in a rather spectacular way that you won’t expect), and you’re free to take in the breathtaking panoramic views covering everything from Manhattan to Brooklyn, the State of Liberty and Jersey. At the top you’ll also find a range of interactive tablets which you can use to learn more about the city skyline and landmarks.

HOW TO DO IT: Standard adult admission is US$34 and can be arranged by your Travel Butler. For a special occasion you can also purchase the City Lights Champagne Nights ticket, allowing you evening entry to the deck plus a glass of Champagne.

Shopping can be found everywhere in New York, but its flagship destination is Fifth Avenue. The most fashionable and retail-heavy part of the Avenue is between 49th and 60th Streets, where a range of large stores including Bergdorf Goodman, Saks Fifth Avenue, Louis Vuitton, Tiffany & Co, and more reside. The street is also home to a 24-hour flagship Apple Store.

Once you’ve tackled the bold and beautiful Fifth Avenue, you’ll enjoy the easy breezy Madison Avenue. No less opulent, Madison Avenue is where you’ll find over 150 luxury boutiques, from big international brands to niche New York designers. Along the strip you’ll find the department store Barneys New York, as well as local boutiques from brands such as Lanvin, Tom Ford, Celine and local brand Proenza Schouler.

DON'T MISS: New York local Ralph Lauren occupies a four-floor flagship menswear store in Madison Avenue, as well as a separate womenswear store located opposite.

New York’s popular theatre district may overlap with London’s West End, but seeing a show on Broadway is still a crowd-favourite, especially when it’s a New York-born show with Tony Awards to boot (Hamilton anyone?).

If you’ve already done the Broadway thing, or simply aren’t a musical person, the Opera is an experience not to be missed. Taking place at the Metropolitan Opera House and Lincoln Center, the Metropolitan Opera is a grand event made even grander by the 1966-era building, featuring opulent chandeliers and red velvet walls. Inside, the impressive theatre continues to host the greats like Aida, La Boheme, Carmen, Madame Butterfly and more. Aim to get there early because the building and the people watching are also fantastic!

DON'T MISS: A guided tour of the Lincoln Center. On this tour you’ll enjoy a behind the scenes peek at where some of the world’s most prestigious singers, musicians and dancers have performed, and learn about the history of the centre and, in turn, New York’s performing arts scene. Walk through the stage door, stand inside the control room and even sit in on rehearsals. On my tour I was lucky enough to sit in on a rehearsal of the New York philharmonic featuring famed cellist Yo-Yo Ma. Tours take around 75 minutes and cost US$25. Talk to your Travel Butler for more details.