Best of New England Fly Drive

  • Boston
  • Portland Maine
  • White Mountains
  • Key West
  • The Berkshires
  • Mystic
  • Yarmouth MA
  • 14 nights from
  • £2,040 per person
  • Trip Code: SD-1038

Holiday Overview

Best Of New England Fly Drive Holiday


Enjoy the best of this charming region of the United States, where rugged shorelines contrast with rolling hills, quaint towns and National Parks. New England is a year round destination, whilst visitors clamour for the spectacular Fall foliage, Spring & Summer visitors can experience beautiful beaches and a wonderful history. Foodies can enjoy the artisan produce of the region year round, with fine seafood and craft beer in abundance.

14 Nights, Start/Finish Boston

Highlights include 

Historic Boston

New England's beautiful coastline

Pretty Vermont & New Hampshire

Best of New England Fly Drive includes:

  • Return flights from the UK
  • Compact Car with Gold Cover - Unlimited mileage, Full tank of fuel, 3 additional drivers, Collision Damage Waiver (CDW), $1 million liability coverage, Zero excess in the USA
  • 3 nights accommodation in Boston
  • 1 night accommodation in Portland
  • 2 nights accommodation in Bar Harbor
  • 2 nights accommodation in the White Mountains
  • 2 nights accommodation in Killington
  • 1 night accommodation in The Berkshires
  • 1 night accommodation in Mystic
  • 2 nights accommodation in Yarmouth

Day 1 - Fly UK to Boston

Arrive in Boston and spend the rest of the day at leisure.

Featured accommodation

Copley Square Hotel


Day 2 - Boston

Enjoy sightseeing at leisure in this fascinating city. History buffs can walk the Freedom Trail a 2.5-mile long path through downtown, that passes by 16 locations significant to the history of the United States. 

Featured accommodation

Copley Square Hotel


Day 3 - Boston

Another full day at leisure to explore this vibrant and cosmopolitan city. Options abound, perhaps take on Old Town Trolley tour, or a sightseeing cruise in the harbor.

Featured accommodation

Copley Square Hotel


Day 4 - Boston to Portland

North of Boston lies almost four centuries of history, as well as some of the coast’s finest beaches and seascapes. First stop is Salem, home of the infamous witch trials. Then drive along the coast to the charming harbor towns of Gloucester and Rockport. Enjoy the oldtime seaport atmosphere of Portsmouth, New Hampshire and its wealth of historic buildings before crossing into Maine. Finishing your day in Portland, Maine’s largest city.


Featured accommodation

Best Western Merry Manor Inn


Day 5 - Portland to Bar Harbor

Continue along the Atlantic Coast to Bar Harbor, pass through the "Lobster Capital of the World" in Rockland. Continue through the picturesque coastal towns of Rockport and Camden before arrival in Bar Harbor.

Featured accommodation

Bluenose Inn


Day 6 - Bar Harbor / Acadia National Park

Spend a full day exploring Acadia National Park. A hike to the top of Cadillac Mountain is rewarded with fantastic coastal views. Stay until late in the day, when the lack of light pollution affords dazzling stargazing.

Featured accommodation

Bluenose Inn


Day 7 - Bar Harbor to White Mountains

Your drive today takes you inland towards the spectacular scenery of the White Mountains, the “rooftop of New England,” a landscape dotted with historic villages and enchanting covered bridges. En route, experience breathtaking views of mountain ranges and pristine forests.

Featured accommodation

The Lodge at Bretton Woods


Day 8 - White Mountains

Spend the full day exploring the beautiful White Mountains.

Featured accommodation

The Lodge at Bretton Woods


Day 9 - White Mountains to Killington

Continue to Vermont and the alpine Green Mountains. 

Featured accommodation

Killington Mountain Lodge


Day 10 - Killington

Spend a full day enjoying the delights of Killington and the Green Mountains, perhaps catch the gondola to the mountain top for some amazing views. Alternatively why not walk a section of the Appalachian Trail which passes nearby. Of course there's always the option to just relax and enjoy the fresh mountain air.

Featured accommodation

Killington Mountain Lodge


Day 11 - Killington to The Berkshires

See picture-perfect villages and some of Vermont’s famous covered bridges before crossing into Massachusetts’ Berkshires, known for their rural beauty and cultural assets. Overnight in the college town of Williamstown.

Featured accommodation

Orchards Hotel


Day 12 - The Berkshires to Mystic

Continue on to Mystic, an attractive seaside village with a rich heritage. Originally one of the area’s most important seaports, its history has been preserved at the Mystic Seaport, one of the country’s largest maritime museums. Visit Main Street, many delicious seafood restaurants, quaint shops and the famous Mystic Pizza restaurant, made famous in the 1988 movie.

Featured accommodation

Inn at Mystic


Day 12 - Mystic to Yarmouth

Turn East and journey towards Cape Cod via Newport, America’s most prominent families, from the Astors to the Vanderbilts have summered in Newport. Some of their spectacular vacation homes are open for viewing. After sightseeing, continue along the coast on your way to Cape Cod.

Featured accommodation

Blue Water Resort On The Ocean


Day 14 - Yarmouth

A full day to explore magnificent Cape Cod with its high cliffs, rolling dunes, broad beaches, miles of walking trails, picturesque villages and delicious seafood. This peninsula is a beloved vacation spot for visitors and natives alike.

Featured accommodation

Blue Water Resort On The Ocean


Day 15 - Return to the UK


Today, leave Cape Cod and drive back to Boston. Return your car at the airport before your departure flight. If time allows stop en route at Plymouth, a living panorama of Pilgrim and Colonial times and see the Mayflower II.

USA Holiday Stopovers

Why not add in the 'Land of the Midnight Sun' - Iceland -on your way to your holiday in the USA. We have put together a great stopover in Iceland for 2 or 3 nights which includes accommodation and the Golden Circle Trip which includes visits to the Gullfoss Waterfall, the geo thermal area of Geysir and Thingvellir National Park.

If you are travelling to the west coast of America, why not add a couple of nights stay in New York which includes accommodation and tickets for the 'Top of the Rock' observation platform for an iconic view of the city skyline. This can be done either on your way out or on the way back.

View USA Holiday Stopovers

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