Boston Holidays
Behind the sheen of skyscrapers that form Boston’s impressive skyline, a city full of history waits to be discovered. One of the oldest cities in America, it’s been the setting of some of America’s defining junctures. Discover the stories of colonial America and explore a city of intrigue on a Boston holiday.
Full of red-brick walkways and brownstone townhouses, Boston is full of charm that tells tales of its revolutionary past. Walk the cobbled streets of Beacon Hill and you’ll find it’s not hard to imagine life in colonial Boston. Wander around North End for a taste of Little Italy, enjoying a coffee and cannoli at Caffe Vittoria, the city’s first Italian cafe, or head to Faneuil Hall Marketplace for some shopping and delicious food. Head just outside of the city and you’ll find the iconic Harvard, one of the United State’s oldest universities. Take a tour around the hallowed institution and uncover yet another facet of Boston’s history.
Discover Boston’s Revolutionary History
Join a tour guide along the Freedom Trail, or go alone and see the sights at your own pace. Weave together the revolutionary stories of Boston’s history and see how America came to be the country we know today. Begin at Boston Common, the oldest park in the United States, before following the red brick trail all the way to Bunker Hill, passing by 14 other important landmarks along the way, including the Old State House and the Old South Meeting House, where the Boston Tea Party began.
Why end your Boston holiday there? To experience even more of the United State’s history, drive or take an Amtrak train to Philadelphia, the home of the Liberty Bell, stopping off in the Big Apple en route. Or explore more of leafy New England, including the charming islands of Nantucket and Martha’s Vineyard, on a multi-centre holiday.
Destination Highlights
Great sample itineraries
Gather inspiration from some of our sample Boston itineraries below and give our Destination Specialists a call and let them put together a Boston holiday just for you.

Boston and Cape Cod Multi Centre Holiday
Discover the best that Massachusetts has to offer with this multi-centre holiday in Boston and Cape Cod. The region of New England is steeped with history and culture and is a spot of sublime natural beauty too. It’s easy to...
Multi centre holidays

New York, Cape Cod, Boston Multi Centre Holiday
For a diverse multi-centre holiday to the United States, combine visits to iconic New York, historic Boston and charming Cape Cod. Begin your American adventure in New York , New York, the city so nice they had to name it...
Multi centre holidays

Best of New England
One of the most picturesque regions of North America, New England is an area of spectacular natural beauty and home to some of the most charming towns and villages in the country. On this wonderful 11 night self drive, you’ll...
Self drive holidays