Boston, Maine and New England Holiday

  • Image
    Tuck into famous Maine lobster | Travel Nation

    Try the famous Maine lobster for dinner

  • Image
    See the beautiful autumn colours in Vermont | Travel Nation

    See the autumn leaves in Massachusetts

  • Image
    Spot whales breaching in the waters off Cape Cod | Travel Nation

    Spot whales breaching in the waters off Cape Cod

  • Image
    Explore Boston's atmospheric Acorn Street | Travel Nation

    Explore Boston's atmospheric Acorn Street

  • Image
    Discover the natural beauty of Acadia National Park | Travel Nation
  • Image
    Hike through the lush forests in the White Mountains

    Hike through the lush forests in the White Mountains

  • Image
    Drive along Cape Cod's beautiful coastline

    Drive along Cape Cod's beautiful coastline

  • Image
    Catch a Red Sox baseball match if you can!

    Boston Red Sox sign, Boston, USA

Tailor-made holidays

Duration(in days): 16

From: UK




Inc. International flights (Per person, based on 2 sharing)

Get a quote

or Call 01273 099433

See more ideas for: USA

    Explore Maine, New Hampshire, Vermont and Massachusetts on this New England holiday. Spend a few days uncovering Boston’s history whilst following the Freedom trail through moments of US history. Explore the wilderness of Acadia National Park and feast on fresh lobster in Maine. Next, drive north into the White Mountains where you can hike and bike to your heart’s content. Swim in the mountain lakes of Vermont before tasting the local cheeses and wine, finishing your time in New England by visiting the pretty towns of the Berkshires and the beaches of Cape Cod. This classic New England self-drive showcases this scenic region at its very best. 

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

    This holiday includes

    • International flights
    • All transfers
    • All accommodation in the USA  
    • Excursions as mentioned in the itinerary
    • Meals as mentioned in the itinerary        

    You’ll remember…

    • Strolling through the picturesque streets of Boston                         
    • Tasting your first fresh lobster roll in Maine
    • Hiking and swimming in Acadia National Park
    • Heading up to the top of Mount Washington
    • Relaxing on the beaches of Cape Cod


    Itinerary in brief:

    • 3 nights Boston
    • 1 night Kennebunkport
    • 2 nights Bar Harbor
    • 2 nights North Conway
    • 2 nights Waterbury
    • 2 nights Williamstown
    • 2 nights Cape Cod

    Day 1: UK to Boston

    Depart the UK from your chosen airport. On arrival in Boston, you will make your own way to your hotel and check in for three nights.

    Included: International flights, 4* hotel   

    Days 2 & 3: Boston 

    Spend a couple of days exploring Boston – we recommend you start by following the Freedom Trail, a route through the city that will take you around 16 different historical sites, from churches and museums to statues and graveyards. For lunch, why not head to the Union Oyster House to try a delicious bowl of New England clam chowder, served here since 1826. Cross the river to explore Cambridge, which is home to both Harvard University and Massachusetts Institute of Technology. In the evening, spend some time strolling the narrow, gaslit streets of Beacon Hill, before settling into a bar and testing some of Boston’s best beers.

    On day three, we’ve included a food tour of the North End, one of the oldest areas of Boston. You’ll taste fresh bread from a small Italian bakery, indulge at an authentic salumeria and sip a delicious cup of espresso. You’ll also stop in at the Old North Church, one of the oldest buildings in North America.  

    Included: 4* hotel, North End food tour 

    Day 4: 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 1 night.

    Included: Car hire, 4* hotel        

    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.

    Included: Car hire, 4* hotel        

    Day 6: Bar Harbor

    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!

    Included: Car hire, 4* hotel        

    Day 7: Drive to North Conway

    Leave the coast behind and drive west to North Conway, in the heart of New Hampshire. On arrival, you’ll check into your hotel for two nights. Why not spend the afternoon exploring this small town, before getting out into the countryside tomorrow?

    Included: Car hire, 4* hotel        

    Day 8: White Mountains

    With a day to explore the White Mountains you’ll want to get stuck into the outdoor activities on offer here straight away. You could go hiking through the forest before swimming or kayaking through one of many high mountain lakes. Another highlight is summiting Mount Washington, whether you tackle the mountain on foot, or head up on the historic cog railway, delivering tourists to the top of the mountain to enjoy stunning views over New Hampshire. Look out for native moose as you drive through the countryside - they are often seen foraging in the lush foothills of the mountains.

    Included: Car hire, 4* hotel 

    Day 9: Drive to Vermont

    Spend the morning taking a final hike through the mountains before driving on to Waterbury in Vermont where you’ll check into your hotel for two nights.

    Included: Car hire, 4* hotel        

    Day 10: Vermont

    Spend today exploring northern Vermont. You could drive up to the lakeside city of Burlington where you can wander through the New England style streets before heading to a beach on Lake Champlain to watch the boats. You could also go fishing or try paddle boarding on one of Vermont’s hundreds of lakes or go cycling through the idyllic countryside. Vermont is also famed for its food and drink – you can visit vineyards, taste artisanal cheeses and learn how traditional maple syrup is made. Waterbury, Vermont is also the home of Ben & Jerry’s ice cream – you can take a tour of the factory and learn how this delicious ice cream is made.

    Included: Car hire, 4* hotel        

    Day 11: Drive to The Berkshires

    This morning you’ll drive south through the Green Mountains before arriving in Williamstown, nestled in the Berkshires in the northwest corner of Massachusetts.

    Included: Car hire, 4* hotel        

    Day 12: The Berkshires

    The Berkshires are a famous retreat for city folks from New York and Boston looking for some nature. Pretty Williamstown comes into its own in fall, when the view of the white church spire amongst the brown, gold and red leaves is an iconic image of New England. Spend some time browsing the antique shops in town before driving through the countryside looking for covered bridges and finishing your time in New England with a world-class meal in one of the Berkshire’s finest restaurants.             

    Included: Car hire, 4* hotel        

    Day 13: Drive to Cape Cod

    Today you’ll drive back to the coast, to Cape Cod. 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.

    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.

    Included: Car hire, 4* hotel        

    Day 14: Cape Cod    

    The day is yours to explore the cape. 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.

    Included: Car hire, 4* hotel        

    Day 15: Depart Boston

    Your time in New England has come to an end – this morning you’ll drive back to Boston Airport, where you’ll return your car hire in time to catch your onwards flight. If you have any time, why not visit Walden Pond on your approach to Boston, the site of Henry David Thoreau’s famous cabin – a sanctuary in the woods around Concord.

    Included: Car hire, 4* hotel, international flights             

    Day 16: Arrive UK

    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
    • International flights
    • Return airport transfers
    • Accommodation as mentioned in the itinerary   
    • Meals as mentioned in the itinerary
    • Excursions as mentioned in the itinerary
    Not included
    • Any meals not mentioned
    • Personal expenses
    • Tips & gratuities
    • Fuel