Boston, Boats & Beaches

Follow your own ‘Freedom Trail’ as you enjoy 14 days immersed in the city streets and sandy shores of New England. Take in the mystery and history of Boston, bursting with fascinating landmarks and cultural hotspots that leave no shortage of ways to spend your days. From a busy metropolis to coastal bliss, this itinerary takes you to picturesque Cape Cod and Martha’s Vineyard, with their fresh seafood, and charming inns, before ending the experience with a few days staying on beautiful Nantucket Island and sailing paradise, Newport.

Number of days Prices from The itinerary includes

14 Days

13 nights / 14 days from £2,260

Prices are per person based on 2 people sharing a Standard Room including economy flights from London.

  • Itinerary starts in Boston and ends in Boston
  • Hotel accommodation as detailed
  • Ferry tickets to Martha’s Vineyard and from Nantucket
  • Inter-island flight
  • Intermediate 4-door car hire with Alamo including insurance and satellite navigation system for 11 days
  • Days 1 to 3


    After arriving at Boston International Airport a private transfer will take you to the Fairmont Copley Plaza for a 3 night stay. Spend the following days exploring the city’s varied sights and attractions, where new and old sit side by side in perfect harmony. Follow the renowned ‘Freedom Trail’ encompassing 16 key sites, sit in a sidewalk café, watch concerts under the stars or go on a whale watching cruise from the historic harbour.

  • Days 4 to 6

    Cape Cod

    Driving Distance : 86 miles / approx. 1 hr 30 mins

    Collect your rental car and head off down to the Cape and arrive at the Wequassett Resort and Golf Club for a 3 night stay. Be beckoned by miles of incredible beaches with days enjoying time on the sands, mealtimes dining on lobster and fresh seafood, or hours perusing the boutiques, galleries and old country stores.

  • Days 7 to 8

    Martha’s Vineyard

    Driving Distance to Hyannis: 20 miles / approx. 35 mins

    Drive to Hyannis, leave the car parked up and take the ferry over to Martha’s Vineyard for a 2 night stay at the Nobnocket Boutique Inn in Vineyard Haven. Far less developed than Cape Cod yet more cosmopolitan than neighbouring Nantucket, Martha’s Vineyard offers the perfect balance. Visit nearby Edgartown and see its boutiques, stately whaling captains’ homes plus charming inns, restaurants and
    bars. Set sail on a sunset cruise through the harbour, cycle miles of picturesque bike paths or why not head out on horseback.