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.
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
Unmissable Experiences
Boston Experiences
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
Unmissable Experiences
Boston Experiences
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
Unmissable Experiences
Portland Maine Experiences
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
Unmissable Experiences
Bar Harbor Experiences
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
Unmissable Experiences
White Mountains Experiences
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
Unmissable Experiences
Killington Experiences
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
Unmissable Experiences
The Berkshires Experiences
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
Unmissable Experiences
Mystic Experiences
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
Unmissable Experiences
Yarmouth Experiences
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.
Copley Square Hotel, Boston Holidays
From the moment it opened in 1891 as the first hotel to grace Boston’s Back Bay, the Copley Square Hotel has served as the face of Boston, and the home-away-from-home of its most famous residents, as well as visiting dignitaries, politicians, businessmen and athletes.
Best Western Merry Manor Inn
Welcome to the Best Western Merry Manor Inn where the service is friendly and the accommodations are comfortable and affordable. This hotel offers convenient access to many local attractions, shopping and dining options in and around Portland
The Lodge at Bretton Woods
In the shadow of Mt. Washington on Route 302, The Lodge is part of the legendary Omni Mount Washington Resort – affording easy access to action-packed activities including everything from skiing, snowmobiling and tubing to hiking, canopy tours and golfing in the summertime.
Killington Mountain Lodge
An authentic Vermont experience, giving you cosy comfort, easy service and stories worth sharing around the fire. S
At the Killington Mountain Lodge every day is an adventure. The views are spectacular and the chances to get outside and enjoy them are even better.
Orchards Hotel
Uncover an oasis of quiet charm, set against the backdrop of the magnificent Berkshire Mountains. The Orchards Hotel, nestled within the picturesque town of Williamstown, Massachusetts, expertly blends old-fashioned New England elegance with modern convenience, creating an atmosphere that is as delightfully esthetic as the area itself.
Inn at Mystic
Situated on fourteen green acres overlooking Fishers Island Sound and Mystic Harbour, the Inn offers relaxing accommodations including rooms with ocean views, jacuzzis, and wood burning fireplaces. Inn at Mystic was once a private estate but it now consists of a hotel, restaurant, mansion, and full service banquet operations. The Inn at Mystic been welcoming guests for over fifty years.
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 My Canada Trips Holidays That May Interest You
Below you will find a small selection of 2024, 2025 My Canada Trips holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 021 7732 and let one of our Canada Holiday experts design the perfect trip for you
USA Road Trips
Pacific Coast Highway Road Trip
- 7 Nights
- Los Angeles
- Pismo Beach
- Monterey / Carmel
- Yosemite National Park
- San Francisco
USA Road Trips
Canyon Adventure Fly Drive Holiday
- 7 Nights
- Las Vegas
- Bryce Canyon
- Moab
- Mesa Verde
- Grand Canyon
USA Fly Drive Holidays
California Fly Drive
- 11 Nights
- San Francisco
- Sonoma
- Lake Tahoe
- Yosemite National Park
- Death Valley
- Los Angeles
- San Diego
USA Road Trips
Blues & Booze USA Road Trip
- 12 Nights
- Chicago
- Indianapolis
- Louisville
- Nashville
- Memphis
- Vicksburg
- New Orleans
USA Fly Drive Holidays
The Wild West Fly Drive Holiday
- 15 Nights
- Denver
- Cheyenne
- Rapid City
- Cody
- Jackson
- Salt Lake City
- Moab
- Durango
- Colorado Springs
USA Fly Drive Holidays
Best of New England Fly Drive
- 14 Nights
- Boston
- Portland Maine
- Bar Harbor
- White Mountains
- Killington
- The Berkshires
- Mystic
- Yarmouth MA
USA Self Drive Holidays
Talkin' Texan Self Drive Holiday
- 12 Nights
- Dallas
- Austin
- Fredericksburg
- Bandera
- San Antonio
- Corpus Christi
- Houston
USA Road Trips
Boston to New York By The Beaches Road Trip
- 8 Nights
- Boston
- Yarmouth
- Martha's Vineyard
- Mystic
- Riverhead
- The Hamptons
- New York
USA Self Drive Holidays
The Classic West Self Drive Holiday
- 13 Nights
- Los Angeles
- Laughlin
- Grand Canyon
- Kayenta
- Lake Powell
- Bryce Canyon
- Las Vegas
- Death Valley
- Yosemite National Park
- Lake Tahoe
- San Francisco
USA Self Drive Holidays
Great Lakes Inn-Sider Self Drive Holiday
- 12 Nights
- Chicago
- Door County
- Middleton
- Winona
- Minneapolis
- Bayfield
- Marquette
- Mackinac Island
- Saugatuck
USA Fly Drive Holidays
Route 66 Fly Drive Holiday
- 15 Nights
- Chicago
- St Louis
- Springfield
- Oklahoma City
- Amarillo
- Albuquerque
- Holbrook
- Williams
- Las Vegas
- Los Angeles
USA Fly Drive Holidays
Western Trails
- 14 Nights
- Salt Lake City
- Lava Hot Springs
- Boise
- McCall
- Coeur d’Alene
- Whitefish
- Helena
- Yellowstone
- Jackson Hole
- Casper
- Cheyenne
- Denver
USA Fly Drive Holidays
Legends and Landscapes of the Old West
- 13 Nights
- Denver
- Cheyenne
- Deadwood
- Minneapolis
- Badlands
- Fargo
- Bismarck
- Medora
- Casper
- Buffalo WY
USA Fly Drive Holidays
Best of the Great American West
- 20 Nights
- Rapid City
- Deadwood
- Medora
- Sheridan
- Billings
- Helena
- Whitefish
- Butte
- Yellowstone
- Cody
- Riverton
- Jackson
- Ketchum
- McCall
- Boise
USA Fly Drive Holidays
Giant Trees and Ancient Forests Road Trip
- 5 Nights
- San Francisco
- Chester, CA
- Lake Tahoe
- Oakhurst
USA Fly Drive Holidays
Explore Kentucky
- 7 Nights
- Newport, KT
- Lexington
- Bowling Green
- Paducah
- Owensboro
- Louisville
USA Self Drive Holidays
Best of Florida Self Drive Holiday
- 9 Nights
- Orlando
- Clearwater
- Naples
- Miami
USA Road Trips
Coasts and Mountains of the South Road Trip
- 7 Nights
- Atlanta
- Asheville
- Charlotte
- Myrtle Beach
- Charleston
- Savannah
USA Road Trips
Wild Wild West USA Road Trip
- 12 Nights
- Los Angeles
- San Diego
- Tucson
- Las Cruces
- Santa Fe
- Durango
- Kayenta
- Williams
- Las Vegas
USA Fly Drive Holidays
The Florida Keys Fly Drive Holiday
- 7 Nights
- Miami
- Islamorada
- Key West
- Key Largo
USA Self Drive Holidays
Volcanic Peaks to Sparkling Shores Self Drive
- 9 Nights
- Portland
- Astoria
- Port Angeles
- Seattle
- Ashford
- Welches
- Grants Pass
- Coos Bay
USA Road Trips
Historic Cities of the Mid-Atlantic Road Trip
- 11 Nights
- Washington DC
- Baltimore
- Philadelphia
- Gettysburg
- Luray
Canada Fly Drive Holidays
Quebec to New England Adventure
- 14 Nights
- Montreal
- Stowe
- White Mountains
- Bar Harbour
- Ogunquit
- Boston
- Green Mountain National Forest
USA Fly Drive Holidays
Great North Music Tour Fly Drive
- 12 Nights
- Chicago
- Detroit
- Cleveland
- Pittsburgh
- Philadelphia
- New York
- Boston
USA Fly Drive Holidays
Route 66 Best of the West
- 14 Nights
- Los Angeles
- Palm Springs
- Kingman
- Williams
- Holbrook
- Santa Fe
- Chicago
USA Fly Drive Holidays
San Antonio & Texas Hill Country
- 9 Nights
- San Antonio River Walk
- San Antonio Hill Country
- Bandera Dude Ranch
- San Antonio
USA Fly Drive Holidays
Utah's Red Rocks and Canyons
- 12 Nights
- Las Vegas
- Zion National Park
- Bryce Canyon
- Torrey
- Moab
- Kanab
USA Self Drive Holidays
Northwest Inn-Sider Self Drive Holiday
- 13 Nights
- Friday Harbor
- Whidbey Island
- Port Townsend
- Cannon Beach
- Portland
- Eugene
- Ashland
- Eureka
- Sonoma
USA Road Trips
Mountains and Canyons Fly-Drive
- 14 Nights
- Denver
- Glenwood Springs
- Moab
- Kayenta
- Page
- Williams
- Las Vegas
USA Fly Drive Holidays
Wonders of Alaska Fly Drive Holiday
- 7 Nights
- Anchorage
- Seward
- Talkeenta
- Denali National Park
Canada Fly Drive Holidays
Eastern Canada and New England Discovery
- 15 Nights
- Toronto
- Ottawa
- Montreal
- Quebec City
- Boston
- New York
- Washington DC
- Niagara Falls