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Beacon Hill, Boston, Massachusetts

Boston to New York

Visit Boston, Plymouth, Sandwich, Cape Cod, Newport, Mystic, The Hamptons & New York.

The iconic cities of Boston and New York via Cape Cod, Newport & The Hamptons

12 Nights from £1,899pp
i
‘from’ prices are based on off peak travel, 2 people sharing a standard car, economy flights and 2-3* Hotels. All trips are completely bespoke so just tell your expert any requirements you have.

Spend seven days discovering all that Boston and New York have to offer, plus five days on the road exploring fancy beach towns like Provincetown, Newport and East Hampton. This is one of our shortest routes at around 500 miles, but it still packs quite a punch as you move between these two bucket-list cities and explore New England’s summer coastal areas. Want to travel during the late autumn or winter months? Then, we can look at alternative route ideas to link Boston and New York, like exploring The Berkshires and Hudson Valley instead for example; let us know if this appeals.

Key road trip highlights:

  • Start your road trip with three nights and two full days exploring the foremost city in New England – Boston.
  • Pit stop in historic Plymouth and Sandwich on your way to Cape Cod. We can also add an overnight stop here if you like.
  • Relax on the beaches and in the quaint upscale towns of Cape Code, Newport and The Hamptons. Plus, if you have additional time and fancy visiting the exclusive island of Martha’s Vineyard, please let us know.
  • Take a ferry across the Long Island Sound to enjoy a shortcut between Newport and The Hamptons.
  • Complete your adventure with at least four nights in the world’s greatest city – New York.
  • What’s included? Direct flights with a premier carrier, accommodation, car rental and a detailed road trip pack.
Boston to New York route with The American Road Trip Company

Our Favourite Hotels

The Civilian Hotel New York City

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The Civilian Hotel

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New York City

Southampton Inn, The Hamptons

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Southampton Inn

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The Hamptons

The Godfrey Hotel Boston

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The Godfrey Hotel

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Boston

The Eliot Hotel, Boston

Hotel:

The Eliot Hotel

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Boston

New York Marriott Marquis, Manhattan Times Square, New York

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New York Marriott Marquis

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New York

Riu Plaza Manhattan Times Square, New York

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Riu Plaza Manhattan Times Square

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New York

The Langham, Boston

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The Langham

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Boston

Gurney's Montauk Resort & Seawater Spa, Hamptons

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Gurney's Montauk Resort

Location:

The Hamptons

Road Trip Itinerary

All of our American road trips can be tailored to meet your requirements. Do you have more or less than 12 days for your road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required.

1

Welcome to Boston, Massachusetts

Today, fly directly into Boston from the UK to start your Boston to New York road trip adventure. After a short transfer from Logan International, you’ll check into your chosen Boston hotel. You’ll have three nights to really get to grips with this beautiful and historic city.

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Boston, MA

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Boston Skyline, Massachusetts, USA
2

Take a walking tour around lovely Boston

Spend your first full day discovering Boston by strolling around Boston Common and Boston Public Garden. After lunch, why not explore the most historic part of Boston, the North End. Famous for its cobbled streets, characterful churches and revolutionary past, you’ll love every minute. During the evening, you can enjoy exceptional New England hospitality in the North End with superb seafood or Italian fare on offer.

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Boston, MA

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Autumn colours in Boston, Massachusetts, USA New England
3

Another day to discover all that Boston has to offer

Discover more of Boston’s must-see sights, including a stroll over Longfellow Bridge, seeking out 17th-Century gravestones and exploring some of Boston’s charming neighbourhoods like Beacon Hill (pictured). If your visit is timed right, we highly recommend getting tickets to a game to cheer on one of Boston’s iconic sports teams.

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Boston, MA

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Acorn Street, Beacon Hill, Boston, Massachusetts, USA
4

Collect your car and cruise over to Cape Cod

Time to start your road trip properly by leaving Boston to head to New York City. The first stop on this short drive is Provincetown at the tip of Cape Cod. Along the way, you’ll visit historic Plymouth, where Pilgrims landed in the Americas on the Mayflower in 1620. Continue through lovely Sandwich, Brewster and further charming Cape Cod villages until you reach the summer hotspot that is charming Provincetown.

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Cape Cod, MA

Drive:

115 miles

Lighthouse in Cape Cod, Massachusetts, New England trip
5

A full day to enjoy the Cape Cod peninsula

Summer home for the Kennedys, Cape Cod is a 65-mile-long peninsula offering historic towns, fantastic seafood and wild sand dunes. It’s popular with New England beachgoers in the summer, whilst spring and autumn also offer visitors enjoyable weather and relaxing coastal surroundings.

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Cape Cod, MA

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Cape Cod, Massachusetts
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Leave Cape Cod for Newport, Rhode Island

Cruise west and leave Cape Cod to enter the smallest of the six New England States, Rhode Island. Once you arrive in Newport, you can park the car again and stroll around this small, charming town searching for delicious seafood and gigantic summer “cottages”. The Breakers (pictured) is the most splendid of Newport’s “cottages” and a mark of the Vanderbilt family’s social and economic dominance during the Gilded Age.

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Newport, RI

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122 miles

Newport RI - The Breakers Mansion
7

From Newport to The Hamptons by ferry and car

Spend the morning relaxing in Newport before heading over Narragansett Bay to Mystic and New London. You’ll then board a car ferry in New London and cross the Long Island Sound to find Long Island in New York State. Once you’re back on dry land, cruise south from the North Fork of Long Island to the exclusive Hamptons area. The villages of Southhampton, Bridgehampton, East Hampton and Montauk will amaze you… which will be your favourite?

Location:

The Hamptons, NY

Drive:

130 miles

Hamptons, New York, USA - House on a beach
8

A full day to see why New Yorkers love the Hamptons

The Hamptons are home to many of the East Coast’s rich and famous. Some of the mansions need to be seen to be believed. Still, this area also offers charming clapperboard cottages, old windmills, and adorable village settings. Cruise around the leafy streets and enjoy picnic lunches by the beach after shopping at the upscale delis and farm shops. Tomorrow, you’ll head back to the buzz of a city, so take a deep breath and soak up the coastal vibes for one last time.

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The Hamptons, NY

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Hamptons, New York, USA - Gardiner Windmill, East Hampton, Long Island
9

Last stop... the one and only New York City

For a more leisurely end to your road trip, leave your car at JFK Airport and take a cab into the hustle and bustle of The Big Apple. Feeling brave, we can arrange for you to drop the car in Manhattan, close to your chosen hotel. After settling into your hotel, consider starting your New York stay by spending the afternoon and evening on the Upper West Side. This part of Manhattan has a relaxed residential feel, combined with foodie institutions like the famous Zabar’s Deli. The American Museum of Natural History can also be found here, and it’s an absolute must-see for all ages.

Location:

New York, NY

Drive:

105 miles

Manhattan, New York to The Hamptons, USA. City Skyline
10

Explore Central Park and the wealthy Upper East Side

Central Park is the most visited urban park in the US, with 843 acres of walking trails, ice rinks, cycle paths, a zoo and even a castle. You can easily spend an entire day here if you wish to. Bordering the eastern side of Central Park is the celebrated 5th Avenue, home to some of the world’s most renowned art museums, such as The Met and The Guggenheim. Madison and Park Avenue are here, too, which are great for watching the wealthiest New Yorkers shop till they drop in extravagant designer stores.

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New York, NY

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Central Park, NYC. New York to LA
11

Discover the joys of Downtown New York

Downtown stretches to Battery Park at Manhattan’s southern tip, where ferries leave to visit the iconic Statue of Liberty and neighbouring Ellis Island. The Financial District is anchored by Wall St, home to the New York Stock Exchange and the National September 11 Memorial and Museum. Surrounding neighbourhoods offer a great contrast to this commercial hub – Soho, Greenwich, Tribeca and the Meatpacking District are all crammed with cool bars, trendy shops and high-quality restaurants.

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New York, NY

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Statue of Liberty, Manhattan, New York City, USA
12

Shopping, sights and skyscrapers in Midtown

New York’s Midtown highlights include 5th Avenue shopping, Grand Central Station, the New York Public Library, Bryant Park, Times Square, Broadway and the Rockefeller Centre – make sure you leave time to visit the Top of The Rock or The Empire State Building as the sunsets, to witness the city’s lights come alive on your final evening in the Big Apple. Tomorrow, you’ll fly home with a suitcase full of memories. Want more time in New York or anywhere else on this road trip? No problem, just let us know.

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New York, NY

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0 miles

Taxi cab in Manhattan, New York, USA

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Frequently Asked Questions

You’ll find answers to most of your questions right here. If you still need assistance, Feel free to get in touch, and we’ll be sure to get back to you promptly!

Can I Add Extra Nights To The Road Trips?

Not a problem. If you are lucky enough to have extra time to explore more places or add more rest days, then just let us know and we’ll adjust your trip to match your preferred timescale.

Must I Have Travel Insurance?

We strongly advise that you purchase travel insurance for your holiday to cover you against medical expenses, theft and other financial costs. Should you need to cancel before travelling, some insurance policies may pay out for any loss of funds that have been paid to us and which cannot be refunded under our cancellation policy.

Can I Do A One-Way Rental?

Many of our trips have a different end destination than the starting point, so this is not a problem. Please note a fee sometimes applies for one-way rentals between other regions or states, which will be paid to the supplier directly when collecting the vehicle. We’ll endeavour to inform you of this charge within your quote.

Am I Limited To Certain Hotels Or Chains?

No, far from it. We work with a range of properties from 3* to 5*, so we can adapt the trip to match most budgets. We have access to rooms in more than 800 hotels, motels, lodges and B&Bs across North America.

How Old Do I Need To Be?

The minimum age to rent a car is 21 in the United States or Canada, although, in addition, any drivers under 25 years of age will generally incur a surcharge.

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Our Trusted Partners And Providers

ARTCo customers can be confident that we only work with the very best service providers, such as Virgin Atlantic, British Airways and Alamo. Any payments made to us are fully protected via the government’s ATOL scheme (Flight packages) or Financial Failure Insurance (Non-Flight Packages).

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