Holiday Overview
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.
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.
Staying at The Revolution 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.
Staying at The Revolution 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.
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.
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.
Staying at 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.
Day 8 - White Mountains
Spend the full day exploring the beautiful White Mountains.
Staying at The Lodge at Bretton Woods
Day 9 - White Mountains to Killington
Continue to Vermont and the alpine Green Mountains.
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.
Staying at 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.
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.
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.
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.
Staying at 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.
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Image Gallery
Portland Head lighthouse
White Mountains
Falmouth
Stockbridge
Freedom Trail
Portland
New England Spting
Boston
Mystic
Fall Colours
Connecticut barn
USA Holiday Stopovers
Why not add in the 'Land of Fire and Ice' - 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.
Alternative Holidays That May Interest You
Below you will find a small selection of 2026, 2027 holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 917 5742 and let one of our Holiday experts design the perfect trip for you
Canyon Adventure Fly Drive Holiday
- Las Vegas
- Bryce Canyon
- Moab
- Mesa Verde
- Grand Canyon
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Buzzing Las Vegas
- Stunning National Parks
7 Nights from £2260pp
Pacific Coast Highway Road Trip
- Los Angeles
- Pismo Beach
- Monterey / Carmel
- Yosemite National Park
- San Francisco
- Receive a free case of wine
- Save £300 per booking book by 31 October
- The exciting buzz of Los Angeles & Hollywood
- California's beautiful coastline
- The stunning natural beauty of Yosemite
- San Francisco with its delightful sightseeing
7 Nights from £2300pp
Best of New England Fly Drive
- Boston
- Portland Maine
- Bar Harbor
- White Mountains
- Killington
- The Berkshires
- Mystic
- Yarmouth MA
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Visit beautiful maritime towns
- See the beautiful mountains of New Hampshire & Vermont
- Experience historic Boston
14 Nights from £2985pp
California Fly Drive
- San Francisco
- Sonoma
- Lake Tahoe
- Yosemite National Park
- Death Valley
- Los Angeles
- San Diego
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Wonderful San Francisco
- Awesome Yosemite
- The heat of Death Valley
- Cool Pacific Breezes
11 Nights from £3100pp
Talkin' Texan Self Drive Holiday
- Dallas
- Austin
- Fredericksburg
- Bandera
- San Antonio
- Corpus Christi
- Houston
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Iconic Texan Cities
- Working Cattle Ranch
- The Alamo
12 Nights from £3145pp
The Wild West Fly Drive Holiday
- Denver
- Cheyenne
- Rapid City
- Cody
- Jackson
- Salt Lake City
- Moab
- Durango
- Colorado Springs
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Wild West Cowboy Country
- Iconic scenery & Wildlife
- National Parks
15 Nights from £3175pp