The Best of Cape Cod & The Islands

9 nights from £2,345 per person

Best time to travel APR - OCT

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Itinerary Highlights

  • Follow the historic Freedom Trail walking route, stroll around Boston Harbor and visit the Boston Tea Museum
  • Feast on clam chowder, relax on endless sandy beaches, visit vibrant Provincetown with its arts, crafts and open-minded attitude
  • Head out in to the bay off Cape Cod on a whale watching adventure
  • Discover quaint towns and villages on the beautiful islands of Nantucket and Martha's Vineyard

What's Included

  • Inspiring Travel Company - Accommodation Throughout Accommodation Throughout
  • Inspiring Travel Company - Car Hire Car Hire
  • Inspiring Travel Company - GPS Device GPS Device
  • Inspiring Travel Company - International Flights International Flights
9 nights from £2,345 per person
Best time to travel APR - OCT
All of our holidays are tailor-made to your requirements by an expert Travel Specialist
Enquire Now Video Consultation

A relaxed fly-drive tour of Massachusett's delightful islands and seaside towns, taking in Cape Cod and the hedonistic town of Provincetown, the quintessential New England island of Nantucket and Martha's Vineyard, a favourite summer island for celebrities.

A perfect summer fly-drive visiting the very best destinations of this area on the East Coast, starting in Boston and travelling onwards to the islands of Cape Cod, Nantucket and Martha’s Vineyard. Begin the holiday with a stay in Boston, exploring the historical sights and many attractions of this cultural hub- perhaps go to a Red Sox game and discover a couple of the 21 neighbourhoods of the city!

Drive onto Chatham in Cape Cod to enjoy the pretty villages and views, staying at a historic hotel. Drive to the tip of Cape Cod to the hedonistic town of Provincetown for its galleries, boutiques, laid-back open-minded attitude and of course whale watching. From Hyannis you will take a ferry to Nantucket, a tiny island with dune-backed beaches, quaint fishing wharves and cobble stoned streets. Hop across to Martha's Vineyard, a celebrity favourite in the summer, encompassing pretty harbour towns, lighthouses, rolling countryside and sandy beaches.


Day 1  UK - Boston
Arrive in Boston - home to the Red Sox, clam chowder and many sights of historical interest. This great city, the unofficial capital of New England, has plenty to offer all visitors.
Day 2  Boston
Enjoy a full day to explore this attractive Atlantic Coast city at your leisure. We suggest you start with the Freedom Trail walk taking you to 16 historically significant sites. Visit the Boston Tea Party Ships and Museum with live reenactments and sample some of the fresh seafood along the waterfront or the famous Boston Clam Chowder. Accommodation: Mandarin Oriental Boston
Day 3  Boston to Chatham, Cape Cod
Chatham, Cape Cod, Massachusetts
Explore the city today by walking the Freedom Trail, a two and a half mile walk that covers 16 historic sites or go on the ‘Hop on, Hop off’ trolley tour. For shopping visit the stores on Newbury Street and the antique shops in Beacon Hill. Enjoy a lunch perhaps of traditional clam chowder, a meal in Quincy Market or Italian cuisine in North End. Drive 89 miles/143 kilometres to Cape Cod and stop off in Plymouth where you can see the replica of the Mayflower, the ship used to transport the pilgrims to the the new world.
Day 4  Cape Cod
Chatham, Cape Cod, Massachusetts
Take the day to enjoy the beautiful area of Cape Cod with its quaint villages. A short walk from the hotel lies the centre of Chatham, a typical New England village by the sea. There are lovely shops, restaurants, inns, white churches, a fishing harbour and a lighthouse.
Staying at  Chatham Bars Inn
Day 5  Provincetown
Provincetown, Cape Cod, Massachusetts
Drive onwards to Provincetown located at the end of Cape Cod. Provincetown is full of artists and fishermen. In the morning, go into the art galleries, dine at small seafood restaurants and walk through narrow streets. In the afternoon, take a whale watching cruise (weather permitting) for a chance to see the humpback whales. In the evening, enjoy dinner in the town or go on the New England Clambake Dune Tour where you can enjoy a clam bake dinner served picnic style coupled with a sunset dune tour.
Staying at  Chatham Bars Inn
Day 6  Nantucket Island
Nantucket, Massachusetts
Start the day early with a drive to Hyannis (car parking fee not included) and take a high speed ferry to Nantucket Island. Walk around and explore America’s most scenic little island! See the cobblestone Main Street with the homes of merchants and captains, the ‘Little Grey Lady’ (the world’s foremost whaling port in the 18th century), ‘Sconset village’ with its cute cottages, Sankaty Head Lighthouse, Cranberry bogs and Nantucket moors.
Day 7  Nantucket
Nantucket, Massachusetts
This attractive island is best explored by bicycle which can be arranged by the hotel concierge. Find a secluded spot on the beach or ride to one of the delightful beachfront restaurants or cafes for lunch. The town is picture postcard cute, and boardwalks take you along the busy harbour and wharves. The hotel offers complimentary use Bike Cruisers so you can explore the area at your lesiure or stay in resort and enjoy complimentary afternoon port and cheese.
Day 8  Martha's Vineyard
Martha's Vineyard, Massachusetts
Drive to Woods Hole for the ferry ride to the island of Martha's Vineyard. Enjoy beautiful ocean views and the surroundings of historic 19th century homes. Walk easily around Edgartown or even explore it by cycle. Spend time relaxing on Martha’s Vineyard, an area visited by many in the summer including celebrities. Explore the island seeing the gingerbread cottages of Oak Bluffs, Gay Head cliffs and lighthouse.
Day 10  Martha's Vineyard to Boston
Spend the morning on Martha’s Vineyard then board the ferry and drive 90 miles to Boston airport for your flight home, or alternatively extend your stay on the island.
The Best of Cape Cod & The Islands
9 nights from £2,345 per person
All of our holidays are tailor-made to your requirements by an expert Travel Specialist
Enquire Now
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