Planning your first trip to New York City is exciting and overwhelming in equal measure. If you’re spending 5 days in New York City for the first time, there’s a mind-boggling number of things to do, see and eat. Planning a 5 day itinerary can seem impossible! I’ve lived in New York City and have used this experience to design what I think is the perfect itinerary for New York City, for first timers. I’ve included the best iconic and historic sights in the city, the best restaurants and bars, a day in Brooklyn, recommended shows & ticketed experiences and the best neighbourhoods in NYC to visit. Reach out if you have any questions, I’m always happy to help!

Day 1: Uptown, Midtown & Central Park

Kick off your time in New York with a bang, and knock off a few iconic sights and destinations on your bucket list. Today is all about Uptown and Midtown Manhattan.

Morning: The Metropolitan Museum of Art

While you’re feeling fresh, tackle the city’s greatest and largest museum: The Met. The Metropolitan Museum of Art is one of the largest museums in the world, so you won’t be able to see it all in one visit. My advice is to pick a few sections that sound the most interesting to you, and enjoy them, rather than rushing around trying to squeeze it all in. My favourite sections to bring visitors to are Egyptian Art (temples!), Medieval Art (especially the Great Hall!), Greek and Roman art and the European Paintings.

Before you leave, head up to The Roof for a great view over the treetops of Central Park (closes in October each year).

Lunch: Head to cosy American bar & brunch spot The Penrose on the Upper East Side or to Saint Ambroeus‘ Madison Avenue outpost for a taste of Milan.

Alternatively, if you’re more into science than art, check out the Natural History Museum, located on the other side of Central Park on the Upper West Side. I prefer The Met, but it depends what you’re into! If you take this option, get a fresh & delicious, quick bite at Daily Provisions on the Upper West Side.

Read more: My favourite museums & galleries in New York City

Afternoon: Central Park

Central Park is the most beautiful part of New York City. Much like The Met, you can’t see it all in one visit, but after several visits I’ve found the perfect tourist trail that shows off some of the prettiest parts.

As you leave the Met, head straight into the park and start heading north, until you reach the Jacqueline Kennedy Onassis Resevoir, which is beautiful during the summer months and absolutely stunning when it’s surrounded by cherry blossoms in Spring. 

Afterwards, head south towards the Central Park Lake, where you’ll also find the Loeb Boathouse, the famous Bow Bridge, the Bethesda Fountain and Bethesda Terrace. If the weather’s nice, you could put your name down for brunch at the boathouse and then hire a boat on Central Park Lake.

At the top of the stairs of Bethesda Terrace, you’ll find the start of the The Mall. Head south down The Mall, which is the iconic Central Park setting so often used in TV shows and movies set in New York. If it’s winter, head a bit further southeast once you reach the end of the mall to visit the Wollman Ice Skating Rink.

Just south of Central Park is the lovely Pulitzer Fountain, right outside the iconic Plaza Hotel. Treat yourself to High Tea or a glass of Champagne in the Palm Court at The Plaza, or book a table at the secret restaurant on Level 7 of luxury department store Bergdorf Goodman for some excellent people watching.

Evening: Broadway

Seeing a show on Broadway is one tourist cliche that is worth every penny. For the 2024 season, catch The Notebook, Liev Schrieber in Doubt, Water for Elephants or Cabaret starring Eddie Redmayne. Find more options on the Broadway website, and buy your tickets through TodayTix for the best prices and easy ticket collection (not sponsored, I just always use them!).

Dinner: Times Square and the Theater District are full of tourist trap restaurants, but locals know there are a few hidden gems. Make a reservation at The Terrace & Outdoor Garden inside the Times Square EDITION hotel. Celebrity sightings are common at The Terrace, which is a gorgeous green oasis on the 9th floor of the hotel, perched above the chaos of Times Square.

Day 2: The Meatpacking, West Village, SoHo & Nolita

Today is all about New York’s most fashionable neighbourhoods, and is one of the best days for just wandering around and enjoying classic New York City neighbourhoods.

Morning: West Village

West Village is one of the most charming and romanticised neighbourhoods in New York City. This well-heeled neighbourhood is full of quiet, leafy streets, stately brownstones and charming neighbourhood cafes and bistros. Head towards West 4th Street Station and wander west to soak up the neighbourhood’s charms.

Brunch: For a perfect West Village brunch, try Jack’s Wife Freda or Joseph Leonard.

Once you’ve finished your West Village wandering, walk downtown towards SoHo via the beautiful Washington Square Park.

Afternoon: SoHo & Nolita

SoHo‘s historic cast iron facades make it one of the most distinctive neighbourhoods in New York City. The streets around Greene St and Mercer Street and particularly pretty. In SoHo, browse the free art galleries like Jeffrey Deitch or check out The Drawing Center, or go shopping. My favourite stores are Frame (denim) and the MoMA Design Store.

Have an early lunch at chic La Mercerie or SoHo Diner for a sleek spin on a a retro diner. Otherwise, save your appetite for Nolita!

Once you’re finished, wander east a couple of blocks to Nolita, a tiny neighbourhood packed with cafes, bars and boutiques. You’ll find lots of skincare, jewellery and perfume stores in Nolita, as well as McNally Jackson, the best book store in New York. On the weekends, there’s a local designer market which mostly has jewellery, running along Prince Street between Mulberry and Mott St. I used to live in Nolita, and absolutely love this neighbourhood!

Lunch:  Grab a slice of the best pizza in New York City at Prince Street Pizza in Nolita. For a sweet treat, try something from Milk Bar, Little Cupcake Bake Shop (I’m obsessed with their banana pudding), Van Leeuwen ice cream or the best cannoli in New York City at Cafe Belle.

If you have time, continue down Mulberry St, past Kenmare and walk south into Little Italy.

Read More:  Nolita Neighbourhood Guide

Evening:  The High Line & Sleep No More

Before you hit the High Line, spend some time exploring The Meatpacking. You could have a drink on the rooftop of the Standard, or get dinner and drinks at Pastis or Catch. Otherwise, you can get dinner later in Chelsea.

The High Line is one of the most popular modern attractions in New York. It’s a free, public garden that has been installed in disused, elevated railway tracks that run from the Meatpacking to Chelsea. Historically, when the Meatpacking was still an industrial neighbourhood, the trains would take meat & other goods out of the Meatpacking and around the city. You can start at either end, but if you start in the Meatpacking, you’ll end up in Chelsea, ready for the rest of the evening’s plans.

Once you’re in Chelsea, you could have a casual dinner at Porchlight. Otherwise, head to the McKittrick Hotel for a drink at one of its gorgeous bars, before Sleep No More starts. Gallow Green is the gorgeous, garden-like rooftop bar that’s opened during the warmer months, and the Manderley Bar is a good option in winter.

Sleep No More is an immersive theatre experience, set in the McKittrick Hotel. It’s a modern re-telling of MacBeth, but instead of sitting passively in the audience, guests and actors roam freely around the hotel. It’s one of my favourite things to do in New York City, as long as you’re up for a couple of hours of chasing actors around a four-storey hotel.

Day 3: Brooklyn

Get off the island today, and explore New York’s capital of cool in Brooklyn. Even though many neighbourhoods like Williamsburg are just as gentrified as Manhattan, there’s still plenty of authentic New York City charm to go around.

Morning: Brooklyn Bridge, Dumbo & Cobble Hill

If you want to walk the Brooklyn Bridge, now’s your chance. Start in the Financial District and walk across the bridge into Dumbo. Alternatively, you can also get a beautiful view by taking the ferry from Wall Street to Dumbo. The fastest way to get to Dumbo is the subway.

Dumbo is a tiny neighbourhood, but it does have the iconic views of the Brooklyn Bridge and back towards Manhattan. You could pick up breakfast at the Time Out Market, or catch an uber to Cobble Hill (it’s a 30 min walk or 20 min subway).

Cobble Hill is Brooklyn’s version of West Village, but with more independent stores. This is such a lovely neighbourhood for wandering! You could eat here, like at Brooklyn Farmacy, or you could pick up some picnic supplies for this afternoon. For a picnic, you could get the best bagels at Shelsky’s, gorgeous baguettes at Bien Cuit, all manner of pastries and dips from the family-run Damascus Bakery and something sweet from One Girl Cookies. While you’re here, check out Books Are Magic, a charming bookshop owned by best-selling local author, Emma Straub.

Afternoon: Picnic in Prospect Park

You might want to catch another Uber, but it will be worth it! Prospect Park is Brooklyn’s answer to Central Park. It’s also adjacent to the beautiful Brooklyn Botanic Garden, so if it’s too cold for a picnic you could head straight to the garden instead, which is beautiful year-round.

Evening: Williamsburg

End your day in Brooklyn with the borough’s original hipster neighbourhood. Start with rooftop cocktails at Westlight, which is on top of the William Vale Hotel. Book if you can, or prepare to queue. The insane views across the East River to Manhattan are worth it! East River State Park has similar views for free. Wander around Bedford Avenue and Wythe Avenue to get a feel for the neighbourhood.

For dinner & drinks, I’d recommend starting at Maison Premiere. This is a gorgeous, old-world bar with a beautiful patio garden and a killer oyster menu. I love getting a tasting plate of oysters from all around North America to compare. For dinner, make a reservation at Misi, and don’t miss their signature sheeps milk ricotta occhi and their olive oil ice cream for dessert. So delicious!

If you wanted to have dinner in Manhattan tonight instead, I’d recommend Estela or Gramercy Tavern which are both New York City icons in their own ways.

Alternatively: Live Sport

Not keen on the Brooklyn Bridge or rooftop cocktails? Book tickets to live sport. In summer, that could be baseball at Yankee Stadium in the Bronx or the US Open at Arthur Ashe Stadium in Queens; in autumn & winter it could mean basketball or ice hockey at Madison Square Gardens or NFL in New Jersey.

Day 4: East Village & Lower East Side 

Get the scoop on New York’s amazing immigrant history and a taste of New York’s most beloved culinary traditions on the Lower East Side today.

Morning: Food Walking Tour

One of the best tours I did in New York City when I lived there was the Urban Adventures Tenements, Tales & Tastes Tour. It starts in the Financial District & ends in the Lower East Side. Your guide will walk you through downtown neighbourhoods, telling the story of immigrant New York with lots of delicious food stops along the way!

Afternoon: Tenement Tour

The tour covers these two spots, but if you didn’t do the tour, get lunch at Russ & Daughters or Katz’ Delicatessen. They’re both iconic, old school New York City delis and close to your next stop.

If you’re a history nerd like me, there’s no better way to step into the past then at The Tenement Museum. Book one of their Apartment Tours to get a guided tour through a traditional tenement building, where the apartments have been restored to showcase the stories of different immigrants in New York at different periods of time. I love these tours and have done two, but if this isn’t your thing you might like to book a spot on the rooftop at Mr Purple instead.

Later: East Village cocktail crawl

Explore East Village, which is home to some of the best bars in New York City. Take a couple of hours to kick back and relax at whatever kind of watering hole tickles your fancy. For smart cocktails, try Death & Co or Angel’s Share, or for something more casual check out the historic McSorley’s Old Ale House or Miss Lily’s.

Evening: Comedy Cellar

Comedy Cellar is the quintessential New York City comedy club. Brick wall, spotlight, and a series of sharp stand up comedians. Weekend shows usually run at around $22, you’ll also need to purchase two items per person during the show (food or drinks), so it ends up around $60-$70pp. You’ll pay for your ticket when you get the final check at the end of the show. Make sure you reserve your tickets in advance!

Dinner & Drinks: Book for dinner at Via Carota or Dante, two West Village darlings that are firm local favourites. For drinks, the original outpost of Employees Only is a classic.

Day 5: Old New York & Midtown Hits

Your last day of this itinerary is teeming with classic New York sights and activities, from Midtown Manhattan to the West Village. Note that you’ll need to book most of these things in advance!

Morning: MoMA or the Morgan Library

The Museum of Modern Art got a major glow up in late 2019. Book tickets in advance, and move this activity to a weekday if you can, to battle less crowds. Alternatively, check out the Morgan Library & Museum which is a smaller and quieter collection, and home to one of the most impressive and glamorous private libraries in New York

Afternoon: Grand Central Station & Bryant Park

First, get lunch. Ess-A-Bagel in Midtown has the best bagels in New York City. If you’ve had enough bagels already, try Qualito Bistro or IRIS for upscale Aegean.

Grand Central Station is one of my favourite places in New York City to take visitors, for the beautiful architecture and hidden surprises within. First, venture deep into the station to find Grand Central Oyster Bar, which has been shucking oysters for New Yorkers for more than 100 years. Next up, admire the constellation painting on the central hall in the main concourse.

Finally, on your way out, stop for a cocktail at The Campbell, once the office an influential New Yorker. Gossip Girl fans might recognise it from the flashback scenes in Season 1.

Afterwards, walk to Bryant Park. I love Bryant Park, it’s one of the loveliest parks in New York City. It’s surrounded by skyscrapers, has beautiful fountains, a lawn and in winter it transforms into a winter village. The Bryant Park Cafe is a great spot for a drink or a bite, if you haven’t eaten earlier.

After the park, head into the adjacent New York Public Library and visit the Rose Reading Room, one of the most beautiful library rooms in the world.

Evening: Top of The Rock or The Empire State Building

Choose between the Empire State Building or the Top of the Rock, because you don’t need to visit both. The Empire State Building is such an iconic observation deck, and is featured in so many films. However, the Top of the Rock has an incredible view of Manhattan, including the beautiful Empire State Building. If it’s your first time in the city, the Top of the Rock would be my choice.

Book tickets in advance and arrive a little before sunset so you can get daytime, sunset and night time views in one trip.

Later, head back to West Village for some live jazz. Live jazz is an iconic experience to have in New York City and there are lots of jazz bars to choose from. None are as legendary as the Village Vanguard. Book your tickets in advance.

For dinner, keep it old school and go to Minetta Tavern.

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That’s it! Have you been to New York City? Is it on your bucket list? Let me know in the comments!