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Cape Cod beach

The Best of Cape Cod & the Islands

11-day tailor-made self-drive from £2,030 pp incl. flights


Short description

A sight-filled road trip taking in New England's energetic cities and peaceful coastal idylls


  • Delve into Boston's historic neighbourhoods and explore America’s most famous university – Harvard
  • Drive out to the pretty fishing villages and historic lighthouses of Cape Cod, a holiday favourite among America's elite
  • Journey by ferry to the islands of Nantucket and Martha’s Vineyard, whose dune-backed beaches are among New England’s most beautiful

In Brief

  • 2 Nights Boston
  • 4 Nights Cape Cod
  • 3 Nights Martha's Vineyard


Recommended for:
August holidays | Best of holidays | History & culture | Natural world | Relaxation | Self-drive

A long-time favourite among America's well-heeled, New England's coast tempts with dune-fringed islands, chocolate-box towns, whale watching tours and some of the east coast's finest and freshest seafood. Featuring stays in Boston, Cape Cod and Martha’s Vineyard, this road trip is the ideal blend of urban vibrancy, seaside relaxation and out-and-about exploration. Enjoy Massachusetts like a local, from the big cities to a classic Cape Cod holiday.

Day by day itinerary

Days 1-2

Depart the UK on a day flight to Boston and make your way to you chosen hotel. The next day you'll follow the Freedom Trail, a well-preserved pedestrian path that weaves in and out of historic neighbourhoods. Take the ’T’ to Cambridge and Harvard University, shop in the upscale boutiques of Newbury Street, explore Boston Common and Copley Square, and wander the cobbled streets of Beacon Hill.

Stay: Wyndham Boston Beacon Hill (Superior) Fairmont Copley Plaza (Deluxe)

Days 3-4
Cape Cod

Collect your hire car and head south to ’the Cape’, stopping en route at Plymouth, the town where the Pilgrim Fathers first settled in the winter of 1620. Then, continue to Chatham for a four-night stay at Chatham Bars Inn, a member of Leading Hotels of the World with sprawling gardens and an acclaimed restaurant and spa. Or, for our lower-priced Superior hotel – Hyannis Harbor Hotel – head towards the island's southern shore at Hyannis. The following day is free to explore Cape Cod's 17th-century villages, lighthouses, pristine sand dunes and sweeping gold-sands coast.

Stay: Hyannis Harbor Hotel (Superior) or Chatham Bars Inn (Deluxe)

Day 5
Cape Cod & optional whale watching

Drive to the northern tip of Cape Cod and spend the morning exploring the art galleries, shops, narrow streets and pretty gardens of Provincetown. This afternoon, perhaps enjoy a whale watching cruise guided by an expert naturalist. This optional tour offers the chance to head out to sea in search of humpback, minke, finback and pilot whales as well as dolphins, porpoises and seals.

Stay: Hyannis Harbor Hotel (Superior) or Chatham Bars Inn (Deluxe)

Day 6
Nantucket Island

Catch the passenger ferry from Hyannis to Nantucket Island to discover one of New England’s most idyllic communities. Explore its cobblestone streets, pretty harbours and near-empty beaches, returning to Cape Cod in the afternoon.

Stay: Hyannis Harbor Hotel (Superior) or Chatham Bars Inn (Deluxe)

Days 7-9
Martha's Vineyard

Drive to Woods Hole for a ferry ride to Martha's Vineyard. A favourite among artists, musicians and celebrities, you'll spend three days enjoying the island’s beautiful beaches, exploring its rolling farmlands and tucking into fresh-from-the-boat seafood in any one of its acclaimed restaurants. Alternatively, rent a bicycle to see the gingerbread cottages of Oak Bluffs and Gay Head cliffs in scenic Aquinnah.

Stay: Nobnocket Boutique Inn (Superior) 

Days 10-11

Enjoy a leisurely morning on Martha’s Vineyard before driving to the ferry and returning to Boston for your flight home, arriving on day 11.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Standard Superior Deluxe

11-day tailor-made self-drive
from £2,030 pp incl. flights


Low Season

from £2,030 pp. incl. flights

High Season

from £3,255 pp. incl. flights


  • Complimentary UK airport lounge access
  • Return flights between the UK and Boston
  • 8 days Compact hire car including personalised road book
  • 9 nights in typical 3* (Standard) and 4* (Superior) accommodation on a room only basis
  • Ferry round trips Nantucket island (passenger ferry) and Martha's Vineyard (by car)

High season: June-September

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

Meet our experts

Speak to a tailor-made specialist on 020 7590 0636

Meet the team

Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

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Let our travel specialists curate the perfect holiday:

  • Inspirational ideas based on experience
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Every step of the way

Every step of the way

Our services are with you from start to finish:

  • Dedicated personal consultants
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