8 day sample itinerary

Boston, Cape Cod and Martha's Vineyard

No trip to the East Coast would be complete without experiencing the history of Boston, mixed with the beauty of Cape Cod and Martha’s Vineyard.

Beginning with Boston, where some of the most historic landmarks await your exploration. You will have a couple of days in Boston, plenty of time to visit the sights which make ‘Bostonians’ very proud to call their city home. Boston has something for everyone, from wandering the Freedom Trail hearing about its revolutionary past, visiting Fenway Park to catch a baseball game or taking a ferry across to Provincetown taking a stroll along Commercial Street.

Just a couple of hours away and you will find yourself surrounded by the unspoilt shores of Cape Cod and the dune-packed beaches of Martha’s Vineyard. Known for the 'Gingerbread Houses', a collection of Victorian houses with intricate detail, Martha's Vineyard's streets are worth taking a wander down to explore the hidden treasures. Finishing up in Cape Cod, hire a bike and cycle along the Shining Sea Bikeway, exploring the 11 miles of seascape on the only bike path to skirt the coast.

Sample Itinerary Summary

We can tailor any part of this itinerary or create a new one just for you.

8 days
Guide Price
£1,889 per person
Price based on
Based on June 19 departure from London Heathrow flying with Virgin Atlantic, staying for 3 nights room only in a Traditional Room (Boston), 2 nights room only in a Standard Room (Martha's Vineyard) and 2 nights room only in a Traditional Room (Cape Cod) including car hire.
Our guide price gives you an idea of pricing which will vary depending on exchange rates, accommodation, duration, dates, airline and cabin class.
Destination Breakdown
Private basis, Self-Guided

Itinerary Breakdown

With plenty on offer in Boston, you will never run out of things to do. Walk the 2.5 miles known as the Freedom Trail, taking in the 16 historical sites from the American Revolution. One thing to take advantage of with Boston is the tax-free shopping. Sport fans can take a tour of America's oldest ballpark, Fenway Park. If in Boston during whale watching season (April to October), take a trip on the numerous boat trips out to try and catch a glimpse of the magnificent marine mammals. Why not take a trip out of the city, a short drive or train ride north of Boston and you will come to Salem, famous for the 1692 witch trials.

Overnight Accommodation

  • Sheraton Boston or similar

Taking the ferry over to Martha’s Vineyard, you will soon notice the contrast between the business of Boston and the beautiful harbour towns of lighthouses you are sailing toward. Take a break at Oak Bluff, a popular holiday destination on the island famed for its character and the picturesque Victorian gingerbread cottages. Regardless of where you are on the island, you will not be too far away from beautiful sandy beaches. There is more to the island than just its beautiful beaches, and if you have the time you must explore the many villages from Edgartown with the charming lighthouse overlooking the harbour, to Tisbury, a perfect location to enjoy the fine restaurants, shops and galleries.

Points of Interest

  • Oak Bluffs
  • Flying Horses Carousel
  • Gingerbread Houses
  • Beaches of Chilmark

Overnight Accommodation

  • Nobnocket Boutique Inn or similar

With miles of unspoilt beaches, you will soon see why Cape Cod is a popular beach destination not just for tourists but for locals too. The stunning beaches are lined with many quaint villages, like Hyannis which offers museums and waterfront eateries. One of the best ways to get around is by bike, as you can cycle along the coast on the Shining Sea Bikeway. You will notice the beautiful lighthouses dotted along the coasts. If you did not get a chance to take the ferry across while in Boston, then a visit to Provincetown is a must. You can visit the hidden 'dune shacks', which have recently become a national landmark as well as being amazed by the flora and fauna.

Points of Interest

  • Hyannis
  • Provincetown
  • John F. Kennedy Hyannis Museum
  • Shining Sea Bikeway

Overnight Accommodation

  • Dan'l Webster Inn and Spa or similar
  • Boston

    Itinerary Highlights

    • Walk the historical Freedom Trail
    • Boston Common
    • Catch a baseball game at Fenway Park
    • Take a ferry across to Provincetown
    • Kayak along the Charles River
  • Martha's Vineyard

    Itinerary Highlights

    • Stroll along the 'Gingerbread Houses' in Oak Bluffs
    • Take a ride on America's oldest carousel, Flying Horses
    • Learn the history of the island at Martha's Vineyard Museum
    • Relax at Chilmark, known for it's panoramic views and coastline
    • Tour the harbour of Edgartown, taking in the charming lighthouse
  • Cape Cod

    Itinerary Highlights

    • Cycle along Shining Sea Bikeway
    • Dine on fresh seafood
    • Take a whale watching tour
    • Ferry around Nobska Point Lighthouse
    • Explore one of the many beaches