Five days in New York City: Beyond the Checklist and Into the Grid
Four nights in Manhattan: the harbour and the memorial, the Lower East Side up to Chelsea, Central Park and the Museum Mile, and a bridge walk into Brooklyn for dinner.
- Length
- 5 days, 4 nights
- Where you stay
- New York City
- Places
- 16 across 5 days

New York is the rare famous city that is not a disappointment in person, and the reason is scale. Photographs flatten it. Standing on Fifth Avenue with forty storeys of limestone on either side and a sliver of sky between them is a physical sensation, not a view, and it is the one thing nobody manages to describe adequately before you get here.
The other surprise is how small Manhattan is. The island is about thirteen miles long and never more than two and a bit wide, and the parts a visitor cares about occupy the bottom half of it. The subway runs all night, costs three dollars a tap and will take you anywhere on this list in under forty minutes, so the whole trip is a series of neighbourhood walks with train rides between them.
Five days is the length at which New York stops being a checklist. Four would get you the landmarks. The fifth is what buys you an afternoon on a bench in Washington Square with a coffee, which is closer to what living here feels like than anything with a ticket queue.
Highlights
- The ferry out to Liberty Island, and the view back at the skyline from the water
- Two reflecting pools where the towers stood, with the names cut through the bronze
- A tenement flat on Orchard Street, left as the families who left it in 1935 had it
- An old freight railway, thirty feet up, planted and turned into a mile-and-a-half walk
- Walking the Brooklyn Bridge east at dusk, with Lower Manhattan lit up behind you
Where to stay

New York City, four nights
Eight and a half million people live in the five boroughs and something like three million of them were born outside the United States, which is the fact that explains most of what the city feels like. People from over 180 countries live here, and the food, the noise and the languages on any given subway car follow from that.
Four nights, all of them in Manhattan, keeps the trip simple: you are never more than half an hour from anything on these five days and you can go back out after dinner. Midtown is convenient and characterless, the Lower East Side and the East Village are the opposite of both, and anywhere on a subway line below 96th Street works. Book early. Rooms are the largest single cost of a New York trip by a wide margin.
Day by day
Day 1 in New York City
Grand Central, Times Square and the Empire State at night
Whatever time you land, this first evening is Midtown, which is where you will probably be sleeping and which is best seen in exactly the order below. It is about a mile and a half in total, all flat, and everything on it stays open late.
Start at Grand Central, walk west, and let the day escalate. The terminal is genuinely beautiful and completely free: come in from 42nd Street, stand at the top of the western stairs and look at the ceiling, which is a green-blue astronomical chart with the constellations painted backwards. Nobody has ever settled whether that was a mistake or a deliberate view from outside the heavens.
Ten minutes further west the character changes entirely. Times Square is loud, aggressively commercial and not really a square, and it is worth twenty minutes after dark and not much more. Go once, at night, when the point of it is obvious.
Then finish high up. The Empire State Building was the tallest in the world when it opened in 1931 and it is still the one the city is shaped around, and the observatories stay open until two in the morning. Go after ten and the queues thin out to almost nothing.
- 17:00
Grand Central Terminal
ArchitectureThe main concourse, with its arched windows and the painted night sky above them, is free to walk into and takes ten minutes. Downstairs is a vaulted food hall and the whispering gallery outside the Oyster Bar, where two people in opposite corners can hear each other perfectly.

- 18:30
Dinner in Midtown
EatThe blocks between Ninth Avenue and Eighth in the Forties are the reliable ones for an early meal, and they are five minutes from the theatres if you have tickets.
- 20:00
Times Square
ArchitectureScreens on every surface, a crowd that never thins, and the closest thing the city has to a theme park. Twenty minutes at night is the correct dose. Ignore anyone in a costume who wants a photograph with you.

- 21:00
Empire State Building
ArchitectureThe 86th floor open-air deck is the one to buy; the 102nd floor is higher, glassed in and rarely worth the surcharge. Last lift up is well after midnight, and a late slot is the difference between a ten minute wait and an hour.
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With more time: If you arrive early enough to have a whole afternoon, the New York Public Library on 42nd Street is two minutes from Grand Central and its reading room is free to walk into.
Day 2 in New York City
Liberty Island, Ellis Island and the memorial
This is the harbour day and the only one with a clock on it. Ferries to Liberty Island leave from Battery Park at the southern tip of Manhattan, security is airport-grade, and the queue at half past eight is minutes long while the queue at eleven is not. Book the earliest sailing you can and be at the pier before it.
The statue was a gift from France for the centenary of American independence and has been on the UNESCO list since 1984, and the thing you are unprepared for is the copper: it arrived the colour of a new penny and took about thirty years of weather to turn green. Pedestal tickets get you inside and onto the balcony. The crown is a separate ticket that sells out months ahead.
The same ferry then calls at Ellis Island, and this is the half of the trip that stays with people. Twelve million immigrants were processed through the main hall between 1892 and 1954, and something like four in ten Americans can trace a relative through it. The registry room is left almost bare, which is the right decision.
Come back to Battery Park in the middle of the afternoon and walk fifteen minutes north to the memorial. Two square voids sit in the footprints of the towers with water falling into them and the names of nearly three thousand people cut through the bronze parapets. It is free to stand there. The museum below is ticketed, takes two hours and is not something to attempt tired.
Then walk east to the bridge. Crossing the Brooklyn Bridge on the raised wooden promenade takes half an hour, the light in the last hour before sunset is the reason to time it this way, and you land in Dumbo with the skyline behind you and dinner in front.
- 08:30
Statue of Liberty
HistoricTake the first ferry from Battery Park. Pedestal access is worth the extra few dollars and is where the view of the harbour opens up; the crown needs booking months out. Allow two hours on the island, including the queue for the boat back.

- 11:30
Ellis Island
NatureThe same ferry ticket covers it, and the immigration museum in the old main building is the better half of the day. The passenger manifests are searchable on site if you know a name and a rough year.

- 14:00
Late lunch back on the island
EatEat when you get back rather than on Liberty Island, where the options are a concession stand. Stone Street, a pedestrianised block five minutes from the ferry terminal, is lined with places with tables outside.
- 15:15
National September 11 Memorial & Museum
HistoricThe memorial pools are open air, free and never closed. Book the museum below if you want it: it is thorough, upsetting and takes about two hours, and it is worth going in with a plan to leave rather than being caught out by how long it takes.
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- 18:00
Brooklyn Bridge
ArchitectureWalk it west to east, on the upper promenade, in the last hour of daylight. It is about 1,600 feet of suspension bridge from 1883 and takes half an hour at a stroll. Stay out of the bike lane, which is enforced by cyclists rather than signs.

- 19:15
Grimaldi's
OtherCoal-fired pizza sold by the pie, no slices and no cards, a few minutes from the Brooklyn end of the bridge. The queue is part of the deal. Whether it is the best pizza in the city is a fight nobody in Brooklyn will let you finish.

With more time: Dumbo repays another half hour after dinner. Walk down to the water at Fulton Ferry Landing for the postcard view back at the bridge, then take the F train home from York Street.
Day 3 in New York City
Orchard Street, Washington Square and the High Line
Today is one continuous walk northwest across the older half of Manhattan, from the tenements to the meatpacking district, and it is the day that explains how the city actually got built. Three and a half miles with long stops in it, or two subway rides if the weather is against you.
Start on the Lower East Side, where the immigrants who came through Ellis Island yesterday ended up. The Tenement Museum is a preserved building on Orchard Street, and it works by taking you into individual flats restored to the year a particular family lived in them. It can only be seen on a guided tour, tours are small and they book out, so buy the ticket the night before at the latest.
Walk west into the Village and the grid falls apart. The streets bend, the buildings drop to four or five storeys, and Washington Square appears with its arch, its fountain and its permanent cast of chess players, buskers and NYU students. Sit down for a while. This is the best free hour in Manhattan.
Keep going northwest to Chelsea. The market in the old Nabisco factory, where the Oreo was invented, is now a block-long hall of food counters, and it is where lunch is. The stairs at the far end lead up to the High Line, an elevated freight line whose last train ran in 1980, replanted as a park thirty feet above the street.
Walk the whole length of it north and you finish at Hudson Yards in the late afternoon, which is a good place to give up and get a train.
- 10:00
Lower East Side Tenement Museum
HistoricGuided tours only, an hour each, in restored flats in a building on Orchard Street that housed some 7,000 people across seventy years. Book ahead. Pick a tour by the family rather than the theme; they are all good and the specific one hardly matters.
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- 12:30
Washington Square Park
LeisureThe arch, the fountain, and a cross section of the city on the benches around it. Costs nothing, needs no plan, and is where you should spend the spare half hour rather than looking for something to do with it.

- 13:30
Chelsea Market
OtherThe old Oreo factory, now a block of food stalls under exposed brick and pipework. Busy at one o'clock and worth timing around. Come out of the north end onto the stairs up to the park.

- 15:00
High Line Park
LeisureA mile and a half of disused freight viaduct, planted and left rough on purpose, running north through and occasionally straight between buildings. Free, open till late, and busiest in the middle. No bikes and no dogs.

With more time: The Whitney Museum sits at the southern end of the High Line, and its outdoor terraces are worth the ticket on their own. Otherwise stay up there until the light goes: the stretch above 30th Street is the quietest and has the best view down the avenues.
Day 4 in New York City
The Met, the park and the spiral
The eastern edge of Central Park between 82nd and 89th Street holds more art than most countries, and today does two of it with the park in between. Take the subway to 86th Street and walk in.
The Met is the one people underestimate. It opened in 1872, occupies hundreds of rooms across two floors, and covers five thousand years, and nobody sees it in a day. So do not try: choose two or three departments before you go in, walk to them and ignore everything else. The Egyptian wing with the Temple of Dendur, the European paintings on the second floor and the American Wing are the usual answer, and the roof garden is open from spring to autumn.
Come out and go straight into the park. Central Park is 843 acres and entirely artificial, dug and planted from swamp and rock in the 1850s and 60s, and the piece to walk to is Bethesda Terrace, ten minutes south of the museum. The fountain in the middle has an angel on it from 1873 and the arcade underneath it has a tiled ceiling that people play music beneath because of what it does to the sound.
Then go back east and north for the Guggenheim, which is the antidote to the Met: one building, one ramp, an hour and a half. Frank Lloyd Wright finished it in 1959, it is a white spiral you walk down rather than up, and the building is at least half the reason to go.
- 10:00
Metropolitan Museum of Art
CulturePick two or three wings before you go in and let the rest go. Tickets are timed and cheaper if you live in New York State, which they check. Three hours is a good visit; a whole day is a bad one.
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- 13:00
Lunch on Madison Avenue
EatThe blocks behind the museum are expensive and pleasant. For something cheaper, buy from a cart on Fifth Avenue and eat it on the museum steps, which is what half of the city does.
- 14:00
Bethesda Terrace and Fountain
OtherThe formal heart of Central Park: a double staircase down to the Angel of the Waters, and an arcade underneath with a ceiling of encaustic tiles that turns anybody playing a saxophone into a much better musician.
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- 15:30
Solomon R. Guggenheim Museum
CultureRide to the top and walk down the spiral. Kandinsky and the rest of the permanent collection are in the side galleries; the rotunda is given over to whatever is on. Open late on Saturdays.

With more time: If the weather is bad, swap the park for the Frick or the Cooper Hewitt, both a few minutes' walk up Fifth Avenue. If it is good, keep walking south through the park and come out at the Plaza, which is about forty minutes and free.
Day 5 in New York City
Modern art and one last view
The last morning is Midtown again, which is convenient for a bag drop and for getting to an airport, and it holds the two things worth saving until now.
MoMA opens at ten thirty and is at its worst by noon, so be there at the door. The trick everybody who lives here uses is to take the lift to the fifth floor and work downward: that is where the paintings people came for hang, and the crowd is still queueing at the ground floor entrance when you get there.
Then walk five minutes west to 30 Rockefeller Plaza and go up. The Top of the Rock deck is on the 70th floor and has the view the Empire State does not, which is the Empire State itself, standing alone in the middle of Midtown with Central Park stretching away behind you the other way. It is the right last thing to see.
Airports from here: allow ninety minutes to JFK or Newark, an hour to LaGuardia, and more of both at rush hour.
- 10:30
Museum of Modern Art
CultureBe at the door half an hour before it opens, go straight up to the top floor and come down through the collection. Two hours is enough. Free entry on Friday evenings, which is also when it is unusable.

- 13:00
Top of the Rock Observation Deck
ArchitectureSeventy floors up, laid out like a ship's deck, and the only high view in the city with the Empire State Building in it. Buy a timed slot; the last hour of daylight is the one everybody wants.
- 14:30
A last bagel
EatBoiled, then baked, and split with cream cheese and lox. Any shop with a queue of people who are not carrying luggage will do.
With more time: With a later flight, St Patrick's Cathedral is across Fifth Avenue and takes ten minutes, and the skating rink and Art Deco lobbies below the deck are free to wander through.
Before you go
Getting in
Three airports serve the city. JFK and Newark take the long-haul flights, LaGuardia is mostly domestic, and all three are run by the same authority and connected to Manhattan by public transport that is cheap and slow or by a taxi that is fast and not. From JFK, the AirTrain to Jamaica and the subway or Long Island Rail Road in is the standard move; from Newark, the AirTrain to the New Jersey Transit line into Penn Station.
Coming by train, you arrive at Penn Station or at Grand Central, and the difference matters: Penn Station is underground and grim, Grand Central is one of the sights on this list. Buses arrive at Port Authority, on the western edge of Times Square.
Getting around
Tap a contactless card or phone on the subway turnstile. A standard fare is three dollars, there are no zones, and after twelve taps in a seven day period the rest of the week rides free, so nobody needs to buy a pass or work anything out in advance.
Above 14th Street the grid does the navigating for you: avenues run north to south, streets run east to west and are numbered, and addresses tell you where they are. Below 14th Street the streets are older than the grid and have names instead, which is why every visitor gets turned around in the West Village at least once.
The distances are deceptive. Twenty numbered blocks make a mile and take about twenty minutes; a crosstown block between avenues is nearly three times as long as a block between streets. Walking twenty blocks up Fifth Avenue is a stroll, walking across the island is a commitment.
Booking, and what will otherwise eat your day
Three things here reward buying a ticket in advance and punish not doing it: the ferry to Liberty Island, the September 11 museum, and any observation deck at sunset. Everything else you can decide on the morning.
The crown of the Statue of Liberty is a separate, much smaller ticket, and it goes months in advance. Pedestal access is easier to get and is where the good view is anyway. Whatever you book, take the first ferry of the day: the security screening at Battery Park runs like an airport and the queue only grows.
When to come, and what it costs
Late April to early June and mid September to early November are the good stretches, with the parks at their best and the humidity gone. July and August are hot and heavy in a way that makes long walking days unpleasant. January and February are cold and cheap, and the museums are wonderful in bad weather.
This is an expensive city and hotels are the reason. Rooms are small and priced by the square foot of Manhattan they sit on, so staying in Brooklyn or Queens, twenty minutes from Midtown on the subway, is the single largest saving available. Food is where you can economise without noticing: a slice of pizza and a bagel are still both cheap, and the best meals in the city are frequently in the least expensive rooms.
The things people remember about New York are almost never the ticketed ones. A subway busker who was genuinely good, an argument overheard at a deli counter, the moment the avenue you are walking down lines up with the sunset.
Leave gaps for that. The landmarks will still be there, and they are not going anywhere in the hour you spend sitting in a park instead.
Make it your trip
Every stop, day and place here lands in your account as an editable trip. Move the days around, swap a city, add your own bookings and costs, and share it with whoever is coming.
Common questions
- Is five days enough for New York?
- It is enough to see the landmarks and still have unscheduled hours, which is the right balance for a first visit. Cut it to four and something has to go, and it is usually the harbour day, which is the one people most regret losing. A week would let you add the Bronx, Queens and a proper day in Brooklyn.
- Where should I stay?
- Anywhere on a subway line below 96th Street in Manhattan, or in Brooklyn just across the river, which is cheaper for the same journey time. Midtown is the most convenient and the least interesting; the Lower East Side and the East Village put you where the restaurants are. Rooms are small everywhere, at every price.
- Do I need to book anything in advance?
- The Liberty Island ferry, the September 11 museum, the Tenement Museum tour and any observation deck at sunset. The Met, MoMA and the Guggenheim take timed tickets but rarely sell out days ahead. Broadway is its own problem: for anything popular, months.
- Is the subway safe?
- Yes, including at night, and it is how nearly everyone gets around. The realistic risk is a bag being taken rather than anything worse, so keep it in front of you on a crowded car. Trains run around the clock, which almost nowhere else in the country manages.
- What about the observation decks, which one?
- Pick two at most. The Empire State is the classic and stays open past midnight; Top of the Rock has the best composition because the Empire State is in it. The newer decks at Hudson Yards and One World Trade are higher and further from anything you recognise.
- Can I use this plan as a starting point?
- Yes. Copy it into a trip of your own and move the days around: the only one with a fixed shape is the harbour day, which needs an early ferry.