Quintessential New England Road Trip

Boston, Maine, New Hampshire & Cape Cod

Best time to travel

Jun - Oct

Ideal length

14 nights

Perfect for

All

From (incl flights)

€2,999 pp

At a glance

International return flights from Dublin to Boston.
Private airport transfers as well as 12 days' pre-arranged car rental in a Hyundai Elantra, or similar.
14 nights’ luxury accommodation in Boston, Scarborough, Jackson, Stockbridge and Sandwich.
Enjoy a private food tour through Boston’s North End and a private tour of Harvard University.
Discover New England’s flora and fauna with a guided canoe tour on the Scarborough Marsh and a Whale Watching Cruise off Cape Cod.

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Introduction

New England is at the heart of historic America. Its verdant mountains and granite shores are home to age-old towns and cutting-edge galleries. On this suggested itinerary, road trip through quintessential small-town New England, spending nights in charming local inns. Begin your journey in New England’s largest city – Boston, Massachusetts. Journey north through coastal towns into Maine, then westwardly into New Hampshire and Vermont before returning south to visit Connecticut and Rhode Island. Return to Massachusetts to discover the charming towns of the Berkshires and Cape Cod.

View all of our luxury holidays to the USA.

Trip Overview

Depart from Dublin to Boston.

Upon arrival, your private driver will be waiting to transfer you to your luxury hotel in the heart of Boston. Your home for the next three nights, explore the historic and gastronomic splendours of New England’s largest city.

Discover the North End on a private food tour.

Boston’s most popular neighbourhood, the North End is home to a wealth of history from the Boston Harbour to Beacon Hall. Make your way through the neighbourhood’s sites, stopping to taste local cheeses, fresh breads, pastries and more.

Visit the Ivy League halls of Harvard.

Enjoy a privately guided tour of the university, hosted by elite students. Dive deep into the rich tapestry of Harvard history as staff entertain and inspire with stories about the university that they call home. Return to Boston to collect your rental car.

Hit the road to Scarborough, Maine.

Enjoy a scenic drive north, passing through the infamous town of Salem. Arrive in Scarborough for a three night stay. This coastal town is on the outskirts of Portland, a historic city with a charmingly restored waterfront.

Journey through the Scarborough Marsh on a guided canoe tour.

Led by a naturalist guide, discover wildlife and plants along the saltwater river habitat. The estuary is particularly popular with birders who come to watch the large variety of waterfowl in the tidal waters and grasses.

Head to Jackson, New Hampshire.

Journey through the White Mountains, admiring the stunning spectrum of colour that underscores the region’s natural beauty. Arrive in the quiet town of Jackson where you will spend the next two nights. Spend days exploring New Hampshire and neighbouring Vermont.

Drive to Stockbridge, Massachusetts.

Tucked into the Berkshire hills, Stockbridge is quintessential small-town New England. The town is famously home to the Norman Rockwell Museum. Spend three nights here, discovering the historic villages and towns of the Berkshires.

Your last New England stop is Sandwich.

Discover the beauty of Massachusetts’ coast as you journey to Cape Cod for a three night stay. The oldest town on the Cape, Sandwich is home to numerous antique shops, art galleries and rare bookstores waiting to be visited.

Embark from Cape Cod in search of whales.

Depart in a state-of-the-art vessel to the Stellwagen Bank National Marine Sanctuary. Considered one of the world’s best whale watching destinations, the area is a seasonal home to humpback, finback, minke whales and several dolphin species.

Drive to the airport for your flight home.

Drop off your rental car and board your flight home. Arrive in Dublin.

Tailoring your holiday

OROKO Itineraries are created with you in mind and no two are the same. These can be used to help plan your trip - or we can design a completely different itinerary to suit you.

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Accommodation

Where to rest your head

Looking for the best accommodation? We've got the contacts

The Whitney Hotel

Situated within Boston’s historic Beacon Hill neighbourhood, the Whitney Hotel is a refined, redbrick property that offers a calming retreat in the bustling city. The hotel embodies the best of period-style.

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Black Point Inn

Black Point Inn is a historic 17th-century property overlooking the Atlantic Ocean and Saco Bay. The property boasts a heated outdoor pool as well as easy access to the nearby beaches.

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Christmas Farm Inn

Located in rural Jackson, Christmas Farm Inn is a charming family-run property that promises a quintessential New England experience. Guests are invited to relax at the luxurious Aveda spa with an indoor pool, hot tub and outdoor pool.

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506 on the River

506 On the River is a boutique inn situated on the banks of the Ottauquechee River, the perfect base for exploring Woodstock. Charmingly designed to capture the spirit of Vermont.

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Red Lion Inn

Located on Stockbridge’s Main Street, the Red Lion is a historic 18th-century inn that is bursting with quaint New England charm. Nearby points of interest include many historical landmarks and museums.

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Belfry Inn

Experience an unforgettable stay at the Belfry Inn of Sandwich, Massachusetts. The inn comprises a converted Catholic church and two homes from different historical periods.

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Frederick William House Inn

Set along Falmouth’s scenic Shining Sea Bikeway, Frederick William House is a converted historical estate that guarantees a luxurious Cape Cod vacation.

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What people are saying

I wanted to thank you and your team for arranging such an amazing holiday. It was just what I needed – so well organised, no stress and such an incredible hotel and location. It was all seamless. I look forward to my next trip!!

Jennifer – Val Thorens, 2023