Boston to New York by the Beaches

  • Connecticut + 3 more
  • Self Drive Ideas
  • 9 Days
from  £885pp
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Two great cities interspersed with seaside resorts.

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


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Day 1 Boston

Arrive Boston and transfer to your hotel. Evening on own to stroll Boston’s lively neighborhoods and discover some of the city’s great restaurants.

Day 2 Boston – Hyannis – Cape Cod / Yarmouth (76mi/122km)

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. Then travel to the neighboring village of Yarmouth. 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.

Day 3 Yarmouth – Provincetown – Yarmouth (93mi/150km)

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 one can take a whale watch or shop its many eclectic art galleries and shops; or spend the day relaxing at your hotel’s sandy beach. Don’t leave New England without feasting on Lobster, steamers, corn-on-the- cob and all the trimmings!

Day 4 Yarmouth – Woods Hole/Martha’s Vineyard Ferry – Martha’s Vineyard (28mi/45km)

Car and passengers drive on board the ferry in Woods Hole for the short, 45-minute ride to Martha’s Vineyard. Take the remainder of the afternoon to relax and familiarise yourself with the area before checking in to your island hotel.

Day 5 Martha’s Vineyard

Today, take a tour of 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 “down-island”, 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. Or explore the island on your own and discover one of the island’s many hidden beaches.

Day 6 Martha’s Vineyard – Woods Hole/Martha’s Vineyard Ferry – Mystic (133mi/214km)

Depart the Vineyard for Connecticut. This afternoon, visit Mystic Seaport, the museum of America and the Sea. Set on 17 acres, it depicts 19th century 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.

Day 7 Mystic – New London/Orient Point Ferry – Riverhead, NY (108mi/174km)

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 drive along the North Fork to visit wineries and explore the region. Then, take two short shuttle ferries to the Hamptons.

Day 8 The Hamptons

Today one can stroll 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 9 Riverhead – New York City (124mi/200km)

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.