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Road Trip from New York to New Haven & Boston: Itinerary & Travel Tips

As amazing, exciting and impressive as New York is – the surrounding States are just as worth seeing. On one of our recent trips to New York we really wanted to take a little road trip.

The destination was quickly decided upon: Boston. After a little research and planning, our small but mighty road trip took shape, which we would like to present to you today: from New York to New Haven and back again via Newport. Perhaps you are planning a similar trip? In this blog article we provide you with lots of helpful info and tips.

1. Useful Knowledge & Initial Tips for your Road Trip from New York to Boston

A road trip from New York City to Boston takes you through four States: Connecticut, Rhode Island (via the coastal route), Massachusetts and of course New York. You will be situated in the region of New England here.

How much time should I plan for the road trip? 

The actual time it takes to drive from New York to Boston is around 3.5 to 4 hours – so really not so far. Still, we would recommend at least three nights for the whole road trip.

You should allow at least two nights for Boston, so you can gain a good initial insight. You could spend another night in Newport on the way back to New York. Of course the more time the better. There are enough great stop offs to stay four or five nights.

Itinerary: Which stops are worthwhile?

We ourselves stopped in New Haven, Boston and Newport – although that is just a small selection of places worth seeing located along the route. (We remind you: four States!)

Additional worthwhile stops are: Hamptons, Providence, Cape Cod and so many more. In addition, it would also be possible to extend your road trip to all of New England and include the States of New Hampshire, Maine and Vermont.

Boston Travel Tips

2. Road Trip Travel Itinerary: New York – New Haven – Boston – Newport

1. Stop: New Haven

From New York the road trip takes you directly to the 130,000-inhabitant city of New Haven. You should allow a good 1.5 hours to drive this stage of the road trip – a little longer depending on traffic.

New Haven itself is only moderately spectacular, although there is one place here that we always wanted to see with our own eyes: Yale University, one of the most prestigious universities in the world.

Our tip: There is a daily (apart from on Sundays) guided tour at midday that takes you around the university campus. The tour takes about an hour. You can find more information here: Yale Campus Tour.

Although you can of course also explore the campus by yourself. The area is huge and there are countless buildings. Hello Gilmore Girls vibes!

Yale Campus

2. Stop: Boston

The road trip continues. The next stage takes us from New Haven to Boston. If you want to avoid road tolls, drive the stretch from Providence to Boston, which takes around 2.5 hours. The inland road via Hartford is a little faster.

Boston is considered one of the most culturally rich cities in the USA. We also really liked the flair with the nice brick houses and green spaces. The historical significance of Boston should also not be forgotten: the protests of the so-called Boston Tea Party triggered the Revolutionary War in the 18th Century.

Our tips for your stay in Boston

Freedom Trail: The perfect start! This famous route goes along a stretch of about 4 kilometres through Boston and connects a total of 16 historical sights with each other including the Boston Common (the oldest public park in USA), the Old State House (the old town hall) and Faneuil Hall. Here you will also find Quincy Market, which is well worth visiting. You can also get a great insight into the city along the Freedom Trail and dive into the history of Boston.

Harvard University: The second university on our road trip is the prestigious Harvard University. We didn’t find the campus as picturesque compared to Yale, but still definitely worth visiting. Like with Yale, there is also a university campus tour here. You can find more info here: Harvard University Tours.

North End:  This district is like the “Little Italy” of Boston. There are not only several Italian restaurants here, but also charming little streets. North End is the oldest residential area in the Boston area.

Massachusetts State House
Boston Quincy Market
Harvard Campus
Harvard Campus

3. Stop: Newport

Before returning to New York, we have one more stop off on our road trip itinerary in the charming coastal town on Newport in the State of Rhode Island. It is actually so nice here that you want to stay longer. You could also plan an overnight stay here.

You can look forward to beautiful coastal landscape in Newport. We definitely recommend the so-called Cliff Walk. It covers a distance of 5 kilometres past famous mansions partly along the cliffs and is simply the perfect experience to get to know Newport.

Probably the most famous property in Newport goes by the name “The Breakers”. If you want to see a mansion up close, this is a good choice. Equipped with an audio guide, you can explore this former stately summer residence.

3. Booking a Rental Car for your Road Trip: Our Tips

Where should I book a rental car in New York?

If you book a rental car in New York, you basically have the option to hire it from the airport or from one of the stations directly in Manhattan.

We ourselves decided to rent directly at the airport (right at the start of our trip). That way we could also avoid the chaotic traffic in Manhattan and the very difficult parking situation.

The most conveniently located airport to reach the first destination of the road trip (New Haven) is LaGuardia Airport, followed by John F. Kennedy International Airport, which is probably more relevant for most.

Tip: we always book our rental cars on this platform

We ourselves always book our cars through Sunny Cars. Sunny Cars is a comparison platform, which compares the different offers of car rental companies for you. You book your rental car on the Sunny Cars website and then pick up your car in New York at a local car rental company (e.g. Avis).

What is the advantage of Sunny Cars? You get fully comprehensive car insurance. In the event of damage, Sunny Cars will reimburse you for the deductible. Believe us: even If you are very careful, a scratch on the car can easily happen. So not having to pay for damage is a real relief.

You can search for cheap rental cars here: Sunny Cars

Road tolls in the USA 

Most roads in the USA are actually toll free, but there are still plenty of stretches that are subject to a toll. You will come across some of these during the road trip from New York to Boston.

Our tip: You can find out exactly where the tolls are along the road here: Car Toll Calculator. On our road trip most were on the bridges, which unfortunately are difficult to avoid. 

It is best to enquire about road tolls when you hire your car. Often you can get flat rate packages rather than paying for each toll section separately, with an additional processing fee (per toll section).

Roadtrip New York Boston

4. Hotel Tips along the Road Trip

New York

We stayed in the wonderful Hotel 50 Bowery in New York City, which we can warmly recommend. The hotel is located in Chinatown, so you can find hip districts such as SoHo or Lower East Side (and therefore also really great cafés and restaurants) right around the corner.

The rooms are beautifully furnished and very comfortable. With a little luck you can also enjoy a dream view from your room. Another highlight is the rooftop bar on the roof. Our conclusion: we would definitely book again!

You can book the hotel here: Hotel 50 Bowery

New Haven

If you want to do an overnight stop in New Haven on your road trip, then we can highly recommend The Blake Hotel. Here you stay right nearby Yale campus.

The rooms are chic, tasteful and comfortable with everything you could wish for. There is a kitchenette with a Nespresso machine in every room. Our conclusion: a pretty boutique hotel to feel at home in!

You can book the hotel here: The Blake Hotel


A good choice in Boston is citizenM Boston North Station. Here you are very centrally located with good value for money for Boston. (Unfortunately hotels are particularly expensive in Boston.)

The rooms are functionally furnished, with a very comfortable feel. You can enjoy a lovely view of the skyline from some rooms. One downside: parking in the nearby parking garage is quite expensive.

You can book the hotel here: citizenM Boston North Station


The dreamy Town & Tide Inn is a highly recommendable place to stay. This great bed and breakfast is very centrally located. For example, you can walk to the start of the Cliff Walks.

The rooms are homely with a touch of maritime flair – simply feel good! The breakfast is fantastic, and the hostess is very accommodating.

You can book the accommodation here: Town & Tide Inn

Disclaimer: Affiliate Links

This travel guide contains our personal recommendations in the form of affiliate links. If you book or buy something through the links, we receive a small commission. This does not change the price for you at all. A million thanks from the both of us!

Have you already been on a road trip from New York to Boston? What did your itinerary look like? Which stops other than New Haven and Newport can you also recommend? We look forward to your additional tips.

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