Boston vs New York: Which City Should You Visit?

Boston and New York are around 230 miles apart, they are nothing alike and I loved them both.

If this is your first trip to the USA, go to New York. If you have been before or you want a smaller, friendlier city and you like old streets and history, go to Boston.

I must admit that the USA would not be my first choice travel destination. I visited New York when my mum wanted to go for her 60th birthday, and I ended up in Boston for a work conference. Yet, I was wow-ed by both cities and would love nothing more than to go back to each.

I would find choosing between them agonising, so the rest of this guide is me trying to be fair to each of them so you can find the city you will love most.

Boston vs New York at a Glance

	Boston	New York
Days you need	3	5
Getting around	Walk almost everywhere	Subway most days
Cost	Expensive	Expensive
Food	Excellent, smaller range	Excellent, huge range
Feel	Quaint, red brick, calm	Busy, always on, metropolitan
History	Colonial and revolutionary	Immigration and the 20th century
Winter	Colder and snowier	Milder
First trip to the USA	No	Yes

Which is better for a first trip to the USA?

New York is iconic in a way almost no other city is. You’ll have seen it in hundreds of films and TV programmes before you land, and walking out into it for the first time is strange in the best way because you already are familiar with many of the sights and sounds of NYC from popular culture.

The scenes I think of are Sally faking it in the deli in When Harry Met Sally. The deli is Katz’s Delicatessen at 205 East Houston Street, and there’s a sign hanging over the table. The fire escape in West Side Story feels like all of NYC. Our apartment rental in the city felt just like this! I loved the dating scene where Tony takes Maria to the Cloisters in Spielberg’s version. The Cloisters is a real museum, up in Fort Tryon Park in Upper Manhattan.

Boston is iconic too, but at a lower level. Harvard is famous. Good Will Hunting was set there. Cheers was set there, although I suspect a lot of people under 40 may not remember this series. It doesn’t have the same pop-culture reach.

If you only get one trip, and you want the version of America you have been picturing your whole life, that is New York.

Which has better food?

New York, but by less than I expected.

New York wins on range. There is more of everything, and you can eat brilliantly at any price. We loved Los Tacos No. 1, Modern Bread & Bagel for the best cream cheese bagel in the city, and Juliana’s in Brooklyn for pizza.

Boston surprised me. It has its own Chinatown and its North End, which is the Italian quarter, and I ate well every single day I was there. Boston is also famous for seafood, which I don’t eat, so I can’t judge on the lobster rolls and clam chowder that it’s really famous for.

Which is cheaper, Boston or New York?

Neither. They are both expensive and you should budget properly before going. You are opening your wallet and accepting the notes are flying out when you visit these cities.

In New York a mid-range hotel will cost you somewhere around $200 a night, and that is before you have eaten anything. Boston is no bargain either, and its hotel prices peak in autumn when leaf-peeping season and the university calendar collide.

Where you can save is the same in both cities. Stay slightly out from the centre and use public transport, eat lunch properly and dinner cheaply, and take a packed lunch on the big sightseeing days. I’ve written more about areas and prices in where to stay in Boston and in my 5 days in New York guide.

Where to Stay in New York

How many days do you need for each?

Five days for New York. Three days for Boston.

Five is the right number for New York. With less than five it becomes a rush unless you are very selective about which sights and neighbourhoods you see.

Boston is much smaller and you can see the centre properly in three days without hurrying. I did it in three and didn’t feel short-changed. You can even get a decent version of it in one day in Boston if that is all you have, which is not something I would say about New York.

Which is easier to get around?

Boston, comfortably.

Boston is a walking city. The centre is small, the Freedom Trail is literally a walking route of the city’s historical sights, and I walked almost everywhere for three days. That changes how a trip feels, because you see the bits in between rather than surfacing from a station.

New York you will be on the subway most days, and that is fine. It is affordable and easier than it used to be now you can tap in with a contactless card or phone using OMNY, and fares are capped over a seven-day window. But it is still a city where you go underground, travel and come back up somewhere else.

Which is more charming?

Boston, easily.

Boston is quaint in a way New York never tries to be. Beacon Hill is red brick and gas lamps and cobbles, and Acorn Street is the most photographed street in the country for a reason. The iconic Beacon Hill Bookstore is beautiful and charming, like walking into a fairytale.

New York is not charming. It is overwhelming, chaotic, busy, always-on, and called the city that never sleeps for a reason. That’s why it’s amazing.

Where to Stay in Boston

Which has better history?

Different history, and you should pick the one you’re most interested in.

Boston is colonial and revolutionary. The Freedom Trail takes you through the beginnings of the United States, and you can walk the whole route in an afternoon.

New York’s history is immigration and the twentieth century. The Statue of Liberty and Ellis Island are the obvious version of that, and the Ellis Island museum was one of the best things we did in New York. Take a packed lunch, because the food out there is poor and expensive.

Is Boston colder than New York?

Yes, and mostly in winter.

	Boston	New York
Average January low	-7°C (19°F)	-3°C (26°F)
Average July high	28°C (82°F)	29°C (84°F)
Annual snowfall	122cm (48in)	64cm (25in)
Sunny days a year	200	224

Summers are near enough identical. Winter is where they separate, and Boston gets almost twice as much snow. If you are travelling in January or February and you don’t like the cold, New York is the softer option.

Which is better in autumn?

Boston, and this is the one category where it wins outright.

New England autumn is a phenomenon and Boston is the easiest city to see it from. Peak colour in the city is usually around the third week of October, and you can get out to the White Mountains or Salem from there. New York in autumn is lovely, and Central Park does turn, but it isn’t the same event.

I’ve gone into the timings properly in Boston in the fall.

Can you do Boston and New York in one trip?

Yes, and if you have the time this is what I would recommend! The two cities are close enough that a multi-centre trip is easy, and they are different enough that you won’t feel like you’ve seen the same place twice.

Fly into one and out of the other. There are direct flights from Heathrow to Boston with British Airways, Virgin Atlantic, Delta, American and JetBlue, around four a day and roughly seven and a half hours, so you don’t need to route through New York to get there. Book it as a multi-city flight rather than two returns and you avoid doubling back.

Getting from Boston to New York

Take the train between Boston and New York. Amtrak runs from Boston South Station to Moynihan Train Hall at New York Penn Station, so you go city centre to city centre with no airport at either end.

Option	Time	Worth it?
Amtrak Acela	About 3 hours 30	Fastest, and the most expensive
Amtrak Northeast Regional	About 4 hours	Cheaper, barely slower. My pick
Bus	About 4 hours 30	Much cheaper again if you’re on a budget
Flying	Short in the air	No. Two airports eat the saving
Driving	About 4 hours	No. You don’t want a car in either city

The Northeast Regional is the sensible choice for most people. It takes about half an hour longer than the Acela and costs a good deal less, and you’re sitting on a train either way. Book ahead, because Amtrak fares climb as the date gets closer, and check current times and prices before you commit.

The same goes in reverse for the New York to Boston train, which runs on the same line.

How long to spend in each

Five days in New York and three days in Boston is the split I’d aim for. That gives you eight days on the ground plus your flights, so about ten days off work.

If you only have a week, do four days in New York and three in Boston. You’ll be selective in New York rather than rushed, and Boston doesn’t need more than three for the main city sights.

If you have ten days or more, keep the five and three and spend the extra time on day trips out of Boston. Salem is close, and the White Mountains are the autumn option for nature lovers.

Which city to do first

I’d land in Boston and fly home from New York.

Boston is a much gentler place to be jet-lagged. It’s small, you can walk it, and nothing about it is overwhelming on day one when you’re waking up at four in the morning. Then you finish on the big one, which is a better shape for a holiday than winding down.

The argument for the other way round is that you hit New York while your energy is highest and end somewhere calm before a seven-hour flight. Both work. I just think Boston is the easier landing.

Boston vs New York: which city should you choose?

Choose New York if it is your first trip to the USA, if you want the famous version of America, if you are a serious foodie, or if you are travelling in winter.

Choose Boston if you have been to the USA before, if you want to walk everywhere, if you like old streets and history, if you only have three or four days, or if you are going in autumn.

If you can do both, do both. I would be sad to give up either one.

More Boston and USA Guides

• Where to Stay in Boston
• One Day in Boston
• A Weekend in Boston
• Boston in the Fall
• 5 Days in New York City
• New York at Night
• The Trader Joe’s Tote Bag
• San Francisco City Guide
• Portland City Guide