Family fly drive: Boston & New England

Trip ideas
Duration (in days): 9

From: Boston

To: Boston



Exc. International flights (per person based on 2 adults, 2 children) 
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Fly drive Boston and New England with our family adventure that includes Boston’s city culture, a scenic national park and plenty of family fun! Begin by exploring Boston’s Freedom Trail and heading out on the water to go whale watching, before driving north to Kennebunkport in southern Maine. Try out your skills on the water in kayaks and boats, because next you’ll be heading to Acadia National Park, where lakes and hiking trails will be your playground for a couple of days. Finish your time in the White Mountains of New Hampshire where you can take the cog railway up to Mount Washington and spot moose on your drive back to Boston. A fantastic intro to New England for the whole family!

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


  • Follow the Freedom Trail through the colonial streets of Boston
  • Enjoy campfire singalongs and roasted marshmallows in Kennebunkport
  • Try some classic New England seafood like lobster rolls and clam chowder
  • Hike and swim in the wild Acadia National Park
  • Take the train to the top of Mount Washington for views over New Hampshire



Itinerary in brief:

  • 2 nights Boston
  • 2 nights Kennebunkport
  • 2 nights Bar Harbor
  • 2 nights North Conway


Day 1: Arrive Boston

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

Day 2: Boston

Spend your first morning in the USA following the Freedom Trail through the city, stopping at important historical buildings and sites, perfect for kids as you quickly move from one interesting monument to the next with no time to feel bored! Wander through Boston Common and see if you can spot the ‘Make Way for the Ducklings’ statues, beloved by children throughout the city. In the afternoon, you’ll head out on the water where we’ve included a whale watching tour - keep an eye out for humpbacks, finbacks and even minke whales. In the evening, why not head into the city for fish and chips or a delicious bowl of local clam chowder?

Day 3: Drive to Kennebunkport

After enjoying the sights of Boston, you’ll head north into the heart of New England, driving up to Kennebunkport on the southern coast of Maine. On arrival, you’ll check into your hotel for two nights.

Day 4: Kennebunkport 

Today you can enjoy the Nonantum Resort, situated on the harbour. This friendly hotel has been welcoming families for years and is only a mile from town so perfectly situated for an early evening stroll for dinner and ice-cream. The day can be spent as you please and believe us, there are so many activities to enjoy here! Choose between hopping aboard a lobster boat, kayaking on the calm water by the resort or sailing down the Maine coast with fabulous views of the ocean. Twice a week the resort hosts a campfire singalong complete with roasted marshmallows – fun for all the family!

Day 5: Drive to Bar Harbor

After a morning of fun, you’ll continue further north in Maine. Drive over the bridge onto Mount Desert Island to the tiny town of Bar Harbor, on the outskirts of Acadia National Park. On arrival, you’ll check into your hotel for two nights. Why not wander into the small town and try the famous Maine lobster for dinner – either in a roll or simply dipped in butter!

Day 6: Acadia National Park

If you can bear to get up early, watching the sunrise from the summit of Cadillac Mountain will ensure Acadia National Park is firmly lodged in your family’s memory. Enjoy the 360-degree views of Bar Harbor, Frenchman Bay and the Cranberry Island, then head down to Sand Beach for a morning walk along the shore, stopping in at one of Bar Harbours little cafes for brunch. In the afternoon, take on one of the many hiking trails that trace their way through the forest, or perhaps drive the scenic Park Loop road. Stop at the multiple pull-outs for stunning views across the ocean - breathing in the pure sea air is good for the soul!

Days 7: Drive to North Conway

Driving west, you’ll make your way into New Hampshire, arriving at the town of North Conway which is nestled in the southern end of the White Mountains. On arrival, you’ll check into your hotel for two nights.

Day 8: White Mountains

The White Mountains are full of fun activities to keep your family busy – whether its biking, hiking or flying through the treetops on a zipline, you’ll never be short of things to do. After a few hours of fun head up to the summit of Mount Washington on the cog railway. On a clear day you can see 6 states and the Atlantic Ocean - before finishing your time here with a plate of delicious local apple pancakes and glass of cool New Hampshire cider to toast a wonderful trip!

Day 9: Depart Boston

Today is your final day in New England – pile everyone into the car and head back to Boston Airport, where you’ll return your rental car and catch your onwards flight.



New England is famous for its four distinct seasons – snowy winters, fresh springs, hot summers and crisp autumns. Spring is a lovely time to travel for quieter roads and new blooms while fall is the busiest (and most expensive) time as crowds descend to see the famous gold and red leaves throughout the forests of New England.

This 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: 

  • Accommodation
  • Car rental
  • Whale Watching Cruise

Not included: 

  • Meals
  • Tips & gratuities
  • Activities at the Nonantum Resort
  • Anything not mentioned above


8 nights in 3* standard accommodation.

Hotels in this category include:

  • Omni Parker House

  • The Nonantum Resort

  • Bluenose Inn

  • The White Mountain Resort & Hotel


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