Boutique Boston to Cape Cod road trip

Trip ideas
Duration (in days): 7

From: Boston

To: Boston



Exc. International flights (per person, based on 2 sharing) 
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Enjoy boutique New England on this short road trip from Boston to Cape Cod. Start in the city of Boston where you can follow the Freedom Trail, enjoy a bowl of clam chowder and take a whale watching tour looking for humpbacks! After a few days in the city, head to the beach, stopping in to see Plymouth Rock and the Mayflower II on the way. Cape Cod is home to endless sand dunes, pretty towns and fresh seafood, so finish your trip by driving along the curved spit of land, passing the iconic lighthouses and enjoying the sea breeze. If want to explore New England in a week, this is the perfect place to start.    

This Boston to Cape Cod itinerary can be tailored to suit your requirements please contact one of our consultants to start planning your dream trip.


  • Wander the Freedom Trail through Boston            
  • Explore the pretty streets of Beacon Hill and Cambridge   
  • Take a whale watching tour on the lookout for humpbacks and minke whales         
  • Browse the boutique shops in Provincetown, in Cape Cod
  • Learn about the colonial history of Plymouth and the Mayflower
  • Enjoy fresh Cape lobster and clams           



Itinerary in brief:

  • 3 nights Boston 
  • 3 nights Cape Cod         


Day 1: Arrive Boston     

On arrival in Boston you will make your own way into the city, where you will check into your hotel for three nights.    

Days 2 & 3: Boston

You have two days to explore the city of Boston, and there’s so much to see! We recommend that you start by following the Freedom Trail, which will guide you around the historical highlights of the city, including Old North Church and Boston Common. Grab a bowl of New England clam chowder for lunch before wandering the pretty streets of Beacon Hill and heading over the river to Cambridge, home to Harvard University and MIT. Try and catch a baseball game at Fenway Park – the field is iconic, as well as the hot dogs!

On your second day we’ve included a whale watching tour – you’ll head out to the Stellwagen Bank, where humpback, finback and minke whales are found in their natural habitat. Hopefully you’ll spot some of these beautiful creatures, whether it’s a tail splash, a fin slap or a full breach – any glimpse will be a thrill.

Day 4: Drive to Cape Cod     

This morning you’ll pick up your car hire and drive to Cape Cod. On the way down, why not stop in at Plymouth, where you can learn about the Mayflower which made the voyage from England with the Pilgrims aboard nearly 400 years ago? Here, you’ll see Plymouth Rock and learn about the history of the “America’s Hometown” before driving on to Sandwich, where you’ll check into your hotel for three nights.

Days 5 & 6: Cape Cod    

Spend a couple of days exploring the cape, whether you’re strolling through the small streets of Provincetown, wandering along the vast sand dunes of the east coast or taking the ferry over to Martha’s Vineyard. There are dozens of nature trails for hiking and cycling, so work out a route that will take you to several of the iconic lighthouses of the Cape, like Chatham Light.

In summer, the beaches of Cape Cod will be packed with day trippers from Boston, so why not join the fun by packing up a picnic and heading for the sand where you can revel in the famous Cape Cod summer vibe? Finish each day with a feast of fried clams, garlic buttered lobster and hot rolls – the perfect accompaniment to a week in New England.

Day 7: Depart Boston   

Your time in New England has come to an end, you’ll now drive back to Boston Airport and drop off your rental car in time for your onwards flight.



New England enjoys glorious summers and cold winters. If you want to visit the Cape to enjoy the pretty beaches then you’ll want to come between May and October and while Boston is definitely a year round destination if you’re arriving in winter you’ll need a warm coat and hat in preparation for some snowy days.

This Boston to Cape Cod road trip is purely a suggestion, and can be tailor-made to your requirements, so please contact us with your dates and requests and we’ll put together a bespoke quotation for you.

What's included: 

  • Accommodation for 6 nights       
  • Car Hire
  • Whale Watching Tour    

Not included: 

  • Fuel       
  • Meals   


6 nights in 4* boutique standard accommodation.

Hotels in this category include:

  • Omni Parker House

  • Belfry Inn & Bistro


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