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Boston to New York By The Beaches Road Trip

  • Boston
  • Yarmouth
  • Martha's Vineyard
  • Mystic
  • Riverhead
  • The Hamptons
  • New York
  • 8 nights from
  • £2,245 per person
  • Trip Code: SD-998

Holiday Overview

Boston to New York - a great USA Road Trip


Journey through some of North America's favourite summer vacation spots, Cape Cod and its fantastic beaches. Ferry to Martha's Vineyard and experience the Hamptons, long established as a bolt hole for New York's rich and famous. 

9 days / 8 nights

Start: Boston

Finish:  New York City 

US States you will visit: Massachusetts, Rhode Island, Connecticut, New York 


Highlights of this trip are:

- Boston Sightseeing 

- The Gingerbread Cottages and fine seafood of Martha's Vineyard

- Seeing the Playground of New York's elite in The Hamptons

Boston to New York By The Beaches Road Trip includes:

  • Return flights from the UK
  • Compact Car with Gold Cover - Unlimited mileage, Full tank of fuel, 3 additional drivers, Collision Damage Waiver (CDW), $1 million liability coverage, Zero excess in the USA
  • Self-Drive Directions and Information Packet at hotel upon arrival
  • 1 night hotel accommodation in Boston
  • 2 nights hotel accommodation in Yarmouth
  • 2 nights hotel accommodation in Martha's Vineyard
  • 1 night hotel accommodation in Mystic
  • 1 night hotel accommodation in Riverhead
  • 1 night hotel accommodation in The Hamptons
  • Ticket for Hyannis Harbour Cruise and Dolphin Fleet Whale Watching
  • Passenger and Vehicle Fare for the Orient
  • Point Ferry and Martha’s Vineyard ferry

Day 1 - Arrive in Boston

Arrive Boston and check into your hotel

Featured accommodation

Colonnade Hotel


Day 2 - Boston-Hyannis-Yarmouth 76 Miles

Travel to Cape Cod. Visit Plymouth en route. Take a Hyannis Harbour boat cruise

Featured accommodation

Blue Water Resort On The Ocean

Unmissable Experiences

Yarmouth Experiences


Day 3 - Yarmouth-Provincetown-Yarmouth 93 Miles

Explore Cape Cod Nat’l Seashore, see lighthouses, coastal villages, take a whale Watch in Provincetown

Featured accommodation

Blue Water Resort On The Ocean


Day 4 - Yarmouth-Martha's Vineyard 28 Miles

Take the ferry to Martha’s Vineyard. Explore the island: Edgartown, Vineyard Haven, Aquinnah Cliffs, Oak Bluffs’ Gingerbread cottages

Featured accommodation

Kelley House Hotel


Day 5 - Martha's Vineyard

Rent a bicycle or moped, go horseback riding, or enjoy one of the may beaches

Featured accommodation

Kelley House Hotel

Unmissable Experiences

Marthas Vineyard Experiences


Day 6 - Martha's Vineyard-Mystic 139 miles

Visit Mystic Seaport, set on 17 acres it depicts 17th century seafaring

Featured accommodation

Inn at Mystic


Day 7 - Mystic-Riverhead 58 Miles

Ferry to Long Island, travel the North Fork stopping at wineries en route.


Day 8 - The Hamptons

Relax on beautiful beaches, stroll charming villages with boutiques and art galleries; tour historic mansions.


Day 9 - Riverhead-New York City 124 Miles - Depart from New York City


Finish in New York City 

USA Holiday Stopovers

Why not add in the 'Land of Fire and Ice' - Iceland -on your way to your holiday in the USA. We have put together a great stopover in Iceland for 2 or 3 nights which includes accommodation and the Golden Circle Trip which includes visits to the Gullfoss Waterfall, the geo thermal area of Geysir and Thingvellir National Park.

If you are travelling to the west coast of America, why not add a couple of nights stay in New York which includes accommodation and tickets for the 'Top of the Rock' observation platform for an iconic view of the city skyline. This can be done either on your way out or on the way back.

View USA Holiday Stopovers

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