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, but with a little strategic planning you’ll be amazed at how many of the best things to see & do in New York City, you can squeeze in.

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.

At the top of each day’s itinerary, I’ve highlighted a summary of the day’s activity in a yellow box, to give you a quick view of the day at a glance. You can also get a free PDF download of the itinerary, with 1 day per page, by joining The Wanderbug mailing list.

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, like West Village, SoHo & Midtown Manhattan.

Reach out if you have any questions, I’m always happy to help!

Day 1: Uptown, Midtown & Central Park

Day 1 Summary: Today’s itinerary includes the Metropolitan Museum of Art, the Upper East Side, Central Park, Times Square & seeing a show on Broadway!

Kick off your time in New York City with a bang, with a few iconic sights and destinations from your bucket list. Today is all about Central Park, Midtown Manhattan & the Upper East Side.

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Morning: Upper East Side & The Met

Breakfast

On weekends, cosy gastropub The Penrose opens at 9:30am. Their Bacon, Egg & Cheese (BEC) is a NYC staple. Otherwise, try H&H Bagels to fuel before a morning at The Met.

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. Book a guided tour of The Met for a deeper insight into what you’re seeing.

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

Lunch at Bluestone Lane

Bluestone Lane does the best Aussie-style coffee in the city. Their Upper East Side cafe offers a full menu and is housed in a 19th-century sandstone building attached to the Church of Heavenly Rest, on the Upper East Side.

Afternoon: Central Park & The Plaza

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 especially stunning when it’s surrounded by cherry blossoms in Spring. 

Afterwards, head south towards the Central Park Lake, where you’ll also find the Central Park 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 & Literary Walk. 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.

High Tea at the Plaza

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 & Times Square

Broadway Show

Seeing a show on Broadway is genuinely one of the best things to do in New York City, and is worth every penny. Catch award-winning musicals in one of the most legendary theatre districts in the world – just make sure you get your tickets in advance!

Dinner above Times Square (trust me!)

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

Day 2 Summary: Today’s itinerary includes the West Village, SoHo, Nolita, Little Italy, The Meatpacking & The High Line.

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

Morning: West Village

Brunch in West Village

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

West Village is one of the most charming and romantic 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.

Washington Square Park

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

Afternoon: SoHo

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 are particularly beautiful.

SoHo Galleries, Shopping & Street Art

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.

Spot major street art at the Gucci Art Wall on the corner of Lafayette & Prince, Pop Art Crying Girl by D*Face at 421 Broome St and a Gigi Hadid mural by Tristan Eaton at 389 Broome St.

Lunch in SoHo

Get lunch at La Mercerie for a chic SoHo cafe, SoHo Diner for a glam diner, or Prince St Pizza for the best slice of pizza in the city (prepare to queue!). Or grab a coffee or pastry at one of Soho’s best bakeries & cafes.

Evening: The High Line & The Meatpacking

The High Line

If you’ve got time before the sun goes down, walk part of the High Line, which starts near Hudson Yards and ends in the Meatpacking District.

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. You don’t need to walk the entire thing from start to finish, instead you can find an entrance gate at a point that suits you. Hopping on at 17th St or 20th St would be plenty if you just want to walk a few blocks of it.

Dinner in the Meatpacking District

Once you’re ready for dinner & drinks, exit the High Line and explore the Meatpacking District. You could have a drink on the rooftop of The Standard, or get dinner at Pastis, Barbuto or Catch. You’ll need a reservation for any of these restaurants.

Day 3: Brooklyn

Day 3 Summary: Today’s itinerary includes the Brooklyn Bridge, Dumbo, Prospect Park & The Brooklyn Botanic Garden, and Williamsburg. Alternatively, this is a good evening to see some live sport!

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

Brooklyn Bridge or Ferry to Dumbo

If you want to walk the Brooklyn Bridge, now’s your chance. Start in the Financial District and walk across the bridge into Dumbo. Personally, I think walking the bridge is overrated and if the weather is good, the view from the ferry from Wall Street to Dumbo is better, but check the ferry times before you leave your hotel. The fastest way to get to Dumbo is the subway.

Dumbo

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 Hills

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: Prospect Park & Brooklyn Botanic Garden

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

Cocktails in Williamsburg

End your day in Brooklyn in the original hipster neighbourhood. Start with rooftop cocktails at Westlight, which is on top of the William Vale Hotel. Book a table, 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.

Dinner & drinks

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 highly recommend Estela or Gramercy Tavern which are both New York City icons in their own ways.

Alternative Plan: Live Sport

Not keen on the Brooklyn Bridge or rooftop cocktails? Book tickets to live sport!

• Baseball: See the Yankees at Yankee Stadium in the Bronx, from late March-October
• Tennis: Catch the US Open at Arthur Ashe Stadium in Queens, from late August-early September
• Basketball: See the New York Knicks play at Madison Square Garden, from October-April
• Ice Hockey: See the New York Rangers play at Madison Square Garden, in Manhattan
• NFL: Catch the New York Giants or the New York jets at MetLife Stadium in New Jersey, from September-January

Find Live Sport Tickets on Ticketmaster

Day 4: Downtown Manhattan (East Village, Lower East Side, Little Italy)

Day 4 Summary: Today’s itinerary includes the Lower East Side, The Tenement Museum, East Village, dinner in West Village & a show at Comedy Cellar.

Morning: Nolita & Little Italy

Breakfast in Nolita

Ruby’s Cafe in Nolita is a neighbourhood favourite. For something more American, try the Grey Dog, or pick up a knish from Yonnah Schimmel’s Knishery for a taste of old New York.

Afterwards, visit the charming Elizabeth Street Garden, or pick up one of the best cannoli in New York City at Cafe Belle, a third-generation pastry shop on Mulberry St. Browse along Mott, Mulberry & Elizabeth Streets.

Little Italy

Walk down Mulberry St into Little Italy, and spot the Audrey Hepburn mural by Tristan Eaton at the corner of Mulberry & Broome.

The Tenement Museum

Spend the rest of the morning on a guided tour at the Tenement Museum, which is of the most incredible experiential museums in New York City. Your guide will take you on a guided tour through a tenement apartment, which has been restored to the original condition and with original artefacts from real families who lived there throughout New York Cit’s history. Pre-booking a tour is essential, it’s very popular!

Afternoon: Lower East Side & East Village

Lunch on the Lower East Side

Get a reuben or a bagel at Katz Delicatessan, a historic deli made a household name by When Harry Met Sally. Don’t lose your ticket! Alternatively, I love the bagels from Russ & Daughters which is in the same area on the Lower East Side.

The Museum at Eldridge St is a stunning synagogue and small museum, and is worth a detour.

East Village

In the afternoon, explore East Village, a storied neighbourhood which is home to some of the best bars in New York City. McSorley’s Old Ale House is one of the oldest bars in the city and feels like it hasn’t changed a bit since it opened in 1854. The offering is very basic, with limited house beer and basic snacks, but it can’t be beat for old school atmosphere.

Also in East Village, you’ll find The Strand Bookstore, which sells new & secondhand books, Tompkins Square Park and picturesque Stuyvesant Place (pictured).

Jump back into the 21st century at Death & Co, which opens at 6pm. It’s one of the most awarded cocktail bars in the world, and if there’s any cocktail bar to visit in New York City, it’s this one.

Evening: Comedy & Jazz in West Village

Stand Up Comedy in West Village

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 in West Village

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

Late night jazz

Catch a late show at The Village Vanguard, New York City’s jazz institution. I love the Village Vanguard Orchestra, which often has a 10pm show, but check their website to find the line up for your visit.

Day 5: Midtown Icons

Day 5 Summary: Today’s itinerary includes MoMa or the Morgan Library, Grand Central Station, Bryant Park, the New York Public Library, and sunset at The Top of the Rock or The Empire State Building, followed by late night jazz in West Village.

Your last day of this itinerary is teeming with classic New York sights and activities, from Midtown Manhattan to the West Village. You 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

Lunch in Midtown

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.

Explore Grand Central Station

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, an upscale cocktail bar in the former offices of an influential New Yorker from the city’s Gilded Age. Gossip Girl fans might recognise the bar from the flashback scenes in Season 1.

Bryant Park & New York Public Library

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.

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 & Flatiron District

Top of the Rock

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.

Flatiron District

Head downtown to the Flatiron District. Take the subway (A or F) from the Rockefeller Center & you’ll be at Eataly in less than 15 minutes!

First, head to Eataly. The multi-level Italian food emporium has to be seen to be believed. Browse the product & small goods, or make a reservation for rooftop drinks.

Swing by the Flatiron Building for the perfect photo moment of the iconic building.

Dinner: Go out with a bang at one of New York City’s classic special occasion restaurants, Gramercy Tavern. This is pure New York!

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