4 Day Boston trip with whale watching

Trip ideas
Duration (in days): 4

From: Boston

To: Boston



Exc. International flights (per person, based on 2 sharing) 
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Experience the historic city of Boston on this short city break. Spend a few days learning about early New England and the Europeans who settled here, strolling through the pretty streets of Beacon Hill and visiting the hallowed field of Fenway Park. On the final day, you’ll set sail for the Cape Cod on a whale watching tour, looking out for humpbacks, finbacks and even the occasional beluga off the coast. In the evening, you’ll return to taste some of New England’s finest seafood - the perfect way to finish off your Boston trip.       

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


  • Explore the historic city of Boston            
  • Stroll through the pretty streets of Beacon Hill     
  • Learn about early settlers in New England             
  • Enjoy a whale watching cruise out to Cape Cod    



Day 1: Arrive Boston     

On arrival in Boston you’ll make your own way into the city and 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 lobster roll or 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 to lovely Cape Cod. 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 in the waves. Whether it’s a tail splash, a fin slap or a full breach – any glimpse will be a thrill!

Day 4: Depart Boston   

Today is your last day in Boston – spend the morning with one last stroll around the harbour before making your own way to the airport 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 it’s best to arrive between May and October, and while Boston is definitely a year-round destination, you’ll need a very warm coat and hat in preparation for some snowy days.

We've done a similar trip...

If you'd like to get a feel for this trip, read our blog post Stopping over in Boston - written by one of our consultants who's been there.

This Boston trip itinerary 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: 

  • 3 nights’ accommodation             
  • Whale watching tour      

Not included: 

  • Meals   
  • Transfers


3 nights in 4* standard accommodation.

Hotels in this category include:

  • Omni Parker House


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