Martha’s Vineyard & the Southern Coast

  • Massachusetts + 1 more
  • Self Drive Ideas
  • 7 Days
from  £625pp
Book today


Drive along New England’s beautiful coastline and on to Martha’s Vineyard.

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.


Book today


Day 1 Boston – Falmouth (74mi/119km)

Arrive Boston’s Logan International Airport and travel south to Falmouth, on Cape Cod for the first night. This evening stroll Falouth’s main street and enjoy some of the local fare.

Day 2 Falmouth – Martha’s Vineyard (5mi/8km – to Woods Hole)

This morning, take the short drive to Woods Hole and drive aboard the Steamship Authority’s ferry for the 45 min. journey to Martha’s Vineyard. Upon arrival, transfer to your hotel. Take the remainder of the afternoon to relax and familiarise yourself with the area.

Day 3 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.

Day 4 Martha’s Vineyard

There’s a variety of recreational activities available on the island. Go horseback riding on the beach at sunset. Look for sunken ships and lost schooners on a scuba excursion, golf, play tennis and relax. Or you may choose to take the ferry to neighbouring Nantucket and stroll its cobblestone streets lined with quaint boutiques.

Day 5 Martha’s Vineyard – Plymouth — Newport (95mi/153km)

Embark on the ferry this morning for the return to the mainland. From Woods Hole travel to Newport via Plymouth, “America’s hometown”. See the Mayflower II, a full size replica of the original ship that carried Pilgrims to the New World, and Plymouth Rock, upon which the Pilgrims first stepped. Continue to the legendary resort town of Newport, filled with the opulence of an earlier period. Enjoy dinner along the harbour this evening. Overnight in downtown Newport for the next two nights.

Day 6 Newport

Tour along Ocean Drive and “Millionaire’s Row” to view the summer cottages of the Gilded Age. Visit the Breakers or the Marble House, both owned by the Vanderbilt family. Newport’s charming Brick Marketplace and waterfront area are filled with shops and restaurants.

Day 7 Newport – Boston (71mi/114km)

Depart Newport for Boston. Stretch your legs along the Freedom Trail to see the important sites from colonial and revolutionary periods. Visit Paul Revere’s House, the Old North Church and tour the USS Constitution, America’s oldest commissioned ship. Then head back to Logan Airport, only 1 mile from the city centre for the departure flight.