Boston to New York By the Beaches

9 nights

Two great cities interspersed with seaside resorts and luxury retreats.

This Boston to New York by the beaches fly-drive holiday does just what it says on the tin. You will be able to compare and contrast Boston and New York but also have time to explore the delights of Cape Cod, Martha’s Vineyard and the Hamptons. Accommodation can be in intimate b&bs or one of the very luxurious resorts that abound in this area. Wherever you stay, the ocean will not be far away; indeed your holiday includes several ferries.

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The Breakdown

Here's a day-by-day guide to your itinerary. Feel free to ask us to add other days or ideas and excursions by adding them to your wishlist, so we can give you the best price.

Day 1


Arrive Boston and transfer to your hotel for a 2 night stay. Evening on own to stroll Boston’s lively neighbourhoods and discover some of the city’s great restaurants.

2 nights in Boston

Day 3

Boston to Hyannis

This morning, depart for Cape Cod. In Hyannis, take a leisurely one hour cruise on Lewis Bay and Hyannis Harbor. The accompanying commentary points out the highlights and interesting anecdotes as you sail past vistas of historical interest, scenic islands and beaches, even two presidential summer homes. Spend two nights in or near Hyannis. Centrally located on Cape Cod, it’s a short drive to all that Cape Cod has to offer; beaches, shopping, golf, biking and hiking trails, and fine dining.

2 nights in Hyannis

Day 4


Today, visit the Cape Cod National Seashore to explore lighthouses, quaint coastal

communities, and natural scenic beauty. Stroll the charming and upscale village of

Chatham before visiting the lively artist colony of Provincetown. Here you can go whale watching, shop the many eclectic art galleries and shops or spend the day on one of the long sandy beaches. Don’t leave New England without feasting on Lobster, steamers, corn-on-the- cob and all the trimmings!

Day 5

Hyannis to Marthas Vineyard

Car and passengers drive on board the ferry in Woods Hole for the 45-minute ride

to Martha’s Vineyard. Take the remainder of the afternoon to relax and familiarize yourself with the area before checking in to your island hotel.

2 nights Marthas Vineyard

Day 6

Marthas Vineyard

Today,  drive around the Vineyard to see a variety of landscapes in the six independent towns whose separate histories form a composite tale of the island’s past. Tour “downisland”, the busy, fashionable eastern half of the Vineyard where Oak Bluffs, Edgartown, and Vineyard Haven lure the rich and famous; and up-island, the sparsely populated and sleepy towns to the west. Aquinnah is known for its beautiful clay cliffs and quiet natural serenity and the beach is one of the few nude beaches left in the U.S.

Day 7

Marthas Vineyard to Old Saybrook

There are plenty of places to stop today.  We would recommend spending time in Providence and Mystic Seaport, the museum of America and the Sea. Set on 17 acres, it depicts 19th c. seafaring life. This evening, visit Foxwoods or Mohegan Sun, the country’s two largest casinos under one roof. Try your luck at gambling or enjoy a show.

Overnight in Old Saybrook, a charming, historical, coastal community.

1 night in Mystic Seaport

Day 8

Old Saybrook to Montauk

It’s a short ride to the Orient Point Ferry where car and passengers board for the short 40 minute trip to the tip of Long Island. Upon arrival visit the North Fork to visit wineries and explore the region. Then, take two short shuttle ferries to the Hamptons, located on the South Fork. Check-in to your waterside hotel, located in the easternmost part of the Hamptons.

2 nights in Montauk

Day 9


Today you can stroll through the charming villages filled with boutique shops and art galleries, have a picnic at an outdoor concert, tour the historic mansions, or just relax on the beach.

Day 10

Montauk to New York City

This morning, travel west toward New York City.

If departing the country today, JFK International Airport is en route, or add on nights in this most iconic of all cities.

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The View

A selection of images representing the areas and places you will be visiting to give you a glimpse of what lies in store during your holiday.

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Now we need to make the perfect holiday for you and give you a quotation.


Whether you would like to book this exact holiday or to tailor-make it to better suit you, please give one of our knowledgeable experts a call on 020 8776 8709 or send us an email.


Alternatively, take advantage of the Wishlist facility; simply add this itinerary, or any particular destinations or hotels to My Wishlist by clicking on the ADD TO WISHLIST buttons on all pages. To make it easier to save and change the details on your Wishlist at any time, why not register with us? You can also just send your completed Wishlist to us at any time; we will then contact you to discuss your holiday further and send you a detailed quotation.


We are here to make sure we tailor-make your holiday to suit your specific requirements and our friendly, knowledgeable staff are all ready to help.


Booking your holiday with us doesn't end when we send your confirmation out to you, either. Talk to us about adding excursions or room upgrades or even restaurant recommendations; we are here to offer advice all the way up to your departure date. Even when you have left the UK, we are still here to help. For example if your flight that we have booked is delayed or cancelled due to ash cloud, strike, etc, it is down to us to re-arrange your travel. We will do everything we can to make sure your holiday runs smoothly. And better still, we are fully bonded with ATOL and ABTA, so your money is completely protected.

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This suggested itinerary is our recommendation but can be tailored to match your requirements

  • We can tailor this trip to suit your specific requirements
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