Self Drive USA: New York to Boston

Trip ideas
Duration (in days): 7

From: New York City

To: Boston



Exc. International flights (per person, based on 2 sharing) 
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Our exciting 7 day USA East Coast self-drive itinerary kicks off with a bang in the Big Apple. Explore Manhattan, hop over to Brooklyn, take in the skyline – so much to see, do and eat.

After a whirlwind stop in NYC collect your rental car and head North into Massachusetts, where you can experience the beaches and beauty of Cape Cod; a laid back lifestyle, creativity in abundance, stunning coastlines and lots of nooks and crannies to explore. Follow the coast north to your final stop, Boston, a wonderful city steeped in history and with great architecture and some leading academic institutions, this often overlooked city has much to offer.

Explore a bite-sized chunk of the East Coast; there is something for everyone on this self-drive, and with plenty of free time you can really make it what you want.


  • Spend 3 nights in the Big Apple exploring this exciting city
  • Scale the Rockefeller Tower for amazing views of New York's skyline
  • Relax on world class beaches in Cape Cod
  • Explore the art havens dotted along the coastline
  • Enjoy an unlimited hop on-hop off Old Town Trolley Tour tour in Boston



Itinerary in brief:

  • 3 nights New York
  • 1 night Cape Cod
  • 2 nights Boston

Day 1: Arrive in New York

We’ve included an arrival shuttle to take you to your Manhattan hotel; New York is the city that never sleeps, so whatever your arrival time you can still get out and explore!

If you want to stretch your legs after the flight then how about hitting Central Park, or taking the High Line walkway that runs along old elevated railway tracks on the West Side from the Meatpacking District to 34th St – giving you a great birds eye view of the city, a little oasis of calm above the iconic taxi-ridden streets.

If you are a foodie, we suggest planning your three days in New York around meal (and snack!) times; there are hot dogs, bagels, deli sandwiches, and cheesecakes just waiting to be enjoyed. Food is a big part of life in New York, so make the most of it!

Day 2: New York

Seeing as New York has an endless amount of things to do, we have included a hop on-hop off bus tour for today. This gives you the opportunity to travel around Manhattan and Brooklyn at your own pace, and stopping at all your must-see attractions. With over 50 stops, this bus tour is ideal for savvy travellers wanting to make the most of their time in the Big Apple. Our highlights include Fifth Avenue, Empire State Building, and the Brooklyn Museum of Art.

You certainly won’t struggle to find something to do in the evening; go to a Broadway show, find a funky little jazz bar, enjoy cocktails on a hotel rooftop terrace (The Hudson is one of our top picks), or simply just walk through Times Square and drink in the lights and vibrant atmosphere.

If you’ve got time why not ride the subway across to Brooklyn; hit Williamsburg for dinner and drinks – it’s a short 15 minute hop and is where the locals go; great restaurants, quirky shops and hipster life at it’s finest.

Day 3: New York

Today we have thrown in a Top of The Rock excursion. This can be used at any time today, and allows you to scale the Rockefeller Tower, where at 70 storeys above the city, you can take in the amazing views of the New York skyline from the Observation Deck. We recommend heading up the tower in the evening, where you can enjoy a stunning sunset over the city.

This is your second day in New York, and the perfect time to monopolize the incredible array of shops on offer. Head to Greenwich Village or SoHo for boutique shops and quirky coffee chops, and at the other end of the scale, Fifth Avenue and Madison Square for big brand shops and luxury jewellery stores.

If shopping isn’t high on your list of things to do, you could pay a visit to some of the cultural attractions in New York, like The Metropolitan Museum of Art, the Museum of Modern Art (MoMA), or the Guggenheim Museum. You can easily spend the day wandering around these fabulous places, and witnessing some spectacular artwork and history.

Day 4: New York to Cape Cod (400km, approximately 4 hours)

It’s now time to collect your hire car and continue on with your journey. You will be driving north out of The Big Apple, and then heading north-east up to Cape Cod. This drive takes approximately 4 hours door-to-door; however we suggest taking the scenic route via Newport, which is a great seaside town and perfect for a lunch stop. There is a really lovely harbour and it’s a great place for an oceanfront walk.

Once you are back on the road, you will reach Cape Cod approximately an hour later. Cape Cod it’s famous for its world class beaches – dramatic dunes and endless stretches of sand, with waters perfect for surfing, swimming, fishing and boating.

The Cape is also a haven for the arts – musicians, artists, writers and photographers flock here, inspired by the landscape and the character of the little towns that dot the coastline.

Day 5: Cape Cod to Boston (100km, approximately 1 hour)

You have all morning to experience what Cape Cod has to offer. We would really recommend driving up the 6A to Provincetown to spend a bit of time there checking out local art, viewing the lighthouse and Pilgrims Monument, and then if you have time visiting Ballston Beach, a huge sandy beach stretching along the Cape Cod coast.

Once you are ready to continue on, take the road out of Cape Cod, and on to Boston. From Provincetown or Ballston Beach the drive will be about two hours, and will take you up the coast and into Boston - “the Cradle of Liberty” where you will drop of your hire car. The name springs from the many historical events and revolutionary meetings that took place in the city in the 1700s.

Day 6: Boston

For your penultimate day, we have included an unlimited hop on-hop off Old Town Trolley tour. This excursion consists of 18 stops, allowing you to explore this historic city at your own pace. Highlights include Faneuil Hall, where the revolutionary leaders urged their fellow colonials to fight for liberty, the historic ballpark - the oldest major league baseball stadium that is still in use, and our favourite, the Cheers Pub – birthplace to the TV sitcom, Cheers.

This tour also gives you the added bonus of free admission at either the Boston Tea Party Ships & Museum, or a Boston Harbor Cruise. Both are fantastic, and the choice is yours.

Day 7: Depart Boston

Sadly your East Coast tour has drawn to a close. Your shared shuttle will pick you up and take you to the airport to board your onward flight today.



Summer on the east coast of the USA runs from around May to September and is the best time to visit to ensure lovely weather, this is peak time however meaning prices will be at a premium and availability limited. Spring and Autumn can be a good option due to milder weather and fewer crowds but avoid winter months if you dont like the cold, it isn't unusual for temperatures to drop below -10c in Boston at this time!

This itinerary is purely a suggestion, and can be tailor-made to your requirements, so please contact us with your dates and requests and we’ll put together a bespoke quotation for you.

What's included: 

  • 6 nights accommodation
  • Shared arrival transfer in New York (upgrade to private available upon request)
  • Shared departure transfer in Boston (upgrade to private available upon request)
  • Hop on – hop off bus tour in New York City
  • Top of the Rock admission
  • Old Town Trolley tour (plus admission for either the Boston Tea Party Ships & Museum, or a Boston Harbor Cruise.
  • 2 day car hire – Compact car with standard insurance (pick up in downtown New York, drop off in Boston)

Not included: 

  • Meals other than those mentioned
  • One way fee of £60
  • Tips and gratuities
  • Personal expenditures
  • Additional tours and excursions not mentioned
  • Parking, fuel and tolls


This package includes 6 nights in 3*/3.5* hotels,

Hotels in this category include:

  • Edison Hotel, New York

  • The Boxer Hotel, Boston



  • The Edison Hotel, New York
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