Trip reference number: 102447

Trip Operator: Wexas Travel

The Best Of Cape Cod & The Islands

From: £1535.00

Holiday overview

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.

Holiday itinerary

Days 1-2: UK/Boston

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 (Standard) 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 – Ocean Edge Resort & Golf Club – head towards the island's northern shore and the seaside town of Brewster. The following day is free to explore Cape Cod's 17th-century villages, lighthouses, pristine sand dunes and sweeping gold-sands coast.

Stay: Ocean Edge Resort & Golf Club, Brewster (Superior) or Chatham Bars Inn (Superior)

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: Ocean Edge Resort & Golf Club, Brewster (Superior) or Chatham Bars Inn (Superior)

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: Ocean Edge Resort & Golf Club, Brewster (Superior) or Chatham Bars Inn (Superior)

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: The Kelley House (Standard) 

Days 10-11: Boston/UK

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.

Holiday pricing


  • 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

This trip has no fixed departures but restrictions may apply - check operator website

** If you see this next to a price, a specific price in your currency has not been provided, this is an estimated-only price based on a currency conversion, the price you pay may be different to that shown

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