Charming New England

12-Day New England Holiday Itinerary - USA

Prices from £2,180 pp

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View day-by-day

Duration12 days / 11 nights (flexible)


ItineraryDamariscotta - White Mountains - Vermont - Newport - Cape Cod - Boston

Suitable for families

Call us 01273 322398


Charming is the best way to describe this region in the northeast of America. Charming towns and small-scale inns with rocking chairs on the veranda, rolling countryside and lighthouses along the lobster-laden coast. From mid-September to mid-October, the leaves on the trees turn from yellow to orange to deep red, creating a spectacular colour palette on the rolling hills in this area.

What's included

  • Accommodation – price based on 2 people sharing
  • Excursions as described below
  • Car hire and insurance – prices may vary depending on departure dates

Our ready-made itineraries 1. Add your favourite itinerary to your travel plan  2. Send it our way 3.Our travel specialists will get planning and send you a quote

Location map

Your day-by-day itinerary

Damariscotta is your Oyster

Upon arrival at the harbour of Damariscotta, you’ll board your accommodation for the next two nights – a private boat with all the mod cons. Olga and Chip provide a warm welcome and the fridge is stocked with cheese and wine, so after you have brought your things on board, you can enjoy a glass of wine on deck while the sun is setting. No need to get sea legs on this boat, as the river is calm and the boat stays safe in the harbour during your stay, if you do want to venture on to dry land, there are restaurants nearby – just follow the sound of the local band.

the sun sets behind a boat

Make your own breakfast the next morning after waking up peacefully on the slow-moving water. Soak up the sun on the deck of the boat or grab one of the kayaks to explore the river up close. In the afternoon, you’ll take a boat trip up the river, sailing past various oyster farms whilst Chip tells you all about the oyster catch on the river and Olga provides you with a snack and drink. There’s more wildlife than just molluscs in the area, so keep an eye out for sea lions or Bald Eagles along the way. After another peaceful night on the water, you’ll step back ashore.

a woman stands on a dock

Rugged Coast of Acadia National Park

Today you will drive through Maine, but may feel like you’re in Canada with the rolling mountains, overgrown with coniferous forests and reflecting lakes. From the White Mountains or western Massachusetts, you’ll drive to the town of Bar Harbor, located on Desert Island, where you will also find most of Acadia National Park. Maine is known for its lobsters, and you can eat them on almost every street corner at simple wooden sheds, meaning you pay a lot less for the delicacy in this part of the world. In the afternoon, visit the Acadia National Park Visitor Centre, so you can make a plan to make the most of the park the following day.

a lighthouse on the shore

Get up early this morning and be one of the first people in the USA to see the sunrise, due to Acadia’s north-easterly location. The National Park extends over several islands of which Desert Island is the largest. Drive along the park roads and you will see one beautiful views over rugged rocks, cliffs and hidden coves. Most tourists head to the major attraction of Cadillac Mountain when arriving in the National Park, so head to the Ocean Path first which is equally as beautiful and a lot calmer in the mornings. Cadillac Mountain is still as enjoyable in the afternoon and will be a lot quieter.

a puffin looking at the flor

To the Top of the White Mountains

Today you’ll head deeper into the interior of New England, where you can hike through snowy hills in winter or swim in a mountain stream in summer. Along the scenic drives you will come across wooden bridges with a roof on top: the covered bridges, characteristic of this region. At the end of the afternoon, stretch your legs in a wooden rocking chair on the porch of your comfortable inn.

a woman looks over the green valley

After a big country-style breakfast the next morning, you will head out to White Mountains State Park. After an hour’s drive you will be at the foot of Mount Washington, where you’ll climb aboard a diesel-powered train that takes you to the top. The old cogwheel train doesn’t go fast, which allows you to look around at the conifers that have taken over the landscape, whilst a guide tells about the area. At the top you can enjoy the views and warm yourself up at the restaurant. In the afternoon, explore the North Conway area further, visiting Diana’s Baths falls in the middle of the forest or following paths over large river boulders and paddling in streams.

a train reached the top of the mountain

The Green Mountains of Vermont

Today it’s time for a road trip straight through the middle of nowhere, it’s a quiet scenic drive from Stockbridge, in western Massachusetts, to a farm in the heart of Vermont. Along the way you’ll pass white churches and bridges covered with small roofs that are typical of this part of the country. After a few hours you’ll arrive at Todd and Suzy’s sheep farm, where you’ll find freshly baked scones waiting for you. Relax on the veranda with a view over the hills or lend a hand feeding the chickens, collecting eggs or taking the sheep to the meadow. You have your own kitchen in your part of the house and there are also excellent restaurants nearby.

a fire pit with chairs on it

After a hearty breakfast say goodbye to the ranch, and drive deeper into Vermont along Route 100. You’ll pass  quaint villages, forests and clear lakes until you reach the Ben & Jerry’s Factory, the perfect place to break up the journey. After visiting the Flavour Graveyard, a cemetery where forgotten flavours are laid to rest, and enjoying a sample, you’ll head on to the the ski resort town of Stowe. Check in at the Von Trapp Family Lodge and you can decide to relax at the pool, go mountain biking, hiking, or in winter you can ski and snowboard to your heart’s content.

autumnal landscape

The Cliff Walk

From Boston, Cape Cod or Martha’s Vineyard, it’s about a 2-hour drive today to the chic seaside town of Newport. So you’ll have plenty of time to grab lunch at the marina where you’ll dine in front of some of the world’s most expensive yachts. In the afternoon, explore Newport on foot wandering past colonial style buildings with wooden facades, heavy shutters and cast iron signboards. Newport is known for its stately mansions and you’ll get to know one very well over the next few nights as you sleep in a luxurious mansion. Its little extravagant in places, but is completely in line with the style of Newport’s golden age.

a traditional mansion

Today it is time to explore Newport’s main attraction, the Cliff Walk along the peninsula’s jagged coastline. Some parts are nicely paved for cycling or walking, others are a bit more rugged and you have to clamber over rocks here and there. No matter the terrain you will see beautiful views, stunning stretches of coastline and impressive mansions. If you want to get a peak inside some more of these striking homes you’ll have a ticket arranged for you to take a look inside eleven public mansions, with their gilded ballrooms and spectacular views over the Atlantic Ocean.

a view of the coastline from above

Relaxing on Cape Cod

It’s now time to slow down the pace, whether you’re arriving from Boston, New York, or Kingston, you’ll notice the more relaxed atmosphere as you cross the bridge on to the Cape Cod Peninsula. This is where the relaxing part of your journey begins. Check into a motel-style hotel with a pool in Hyannis, the perfect base for a visit to Cape Cod with nice cafes and restaurants in the city centre. There is a lot to do on Cape Cod and the peninsula is small so exciting day trips are always just around the corner.

water passes past a rock

Today you are free to do as you please, if the sun is shining then it is time to head to one of the many beaches. For a quieter option you can venture to Cape Cod National Seashore, you pay an entrance fee but it is well worth it with many lighthouses, beaches, forests and lakes throughout. If you go to Nauset Light Beach you can swim and dive with the waves or you’ll find calmer waters in Cahoon Hollow Beach, which is ideal for sun lovers and a great place to grab a bite to eat, try the Beachcomber restaurant.

a group sit on chairs on the beach

Speak to our USA specialist, Emma

Start planning your next adventure with Emma, our travel specialist for the USA. She'll work with you until your itinerary is exactly how you want it, leaving you to enjoy your holiday, stress-free.

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