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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

  • Follow the Freedom Trail, a path that will lead you to 16 of the city’s important historic sites
  • Wander the charming neighbourhood of Beacon Hill, home to the Massachusetts State House
  • Shop at the historic Faneuil Hall Marketplace
  • See the Red Sox in action at Fenway Park

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.

Ocean Park

Two Centre Holidays Boston And Cape Cod

  • 8 Days
  • Guide Price £2,099 PP
Discover the best that Massachusetts has to offer with this multi-centre holiday in Boston and Cape Cod. The region of...
View Multi Centre
Multi centre holidays

New York And Boston Multi Centre Holidays

  • 10 Days
  • Guide Price £2,099 PP
For a diverse multi-centre holiday to the United States, combine visits to iconic New York, historic Boston and charming Cape...
View Multi Centre
Multi centre holidays
Martha s Vineyard

New England Self Drive Holidays

  • 12 Days
  • Guide Price £2,099 PP
One of the most picturesque regions of North America, New England is an area of spectacular natural beauty and home...
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Self drive holidays

Explore Boston

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Baseball Red Sox Fenway Park Boston Cr M

Fenway Park

A visit to Fenway Park is a must for sports fans. Mingle with the locals, enjoy a beer and a hotdog and take in a baseball game. In off season, take a one hour tour of one of the oldest baseball parks in history.

Freedom Trail Marker

The Freedom Trail

Walk the famous Freedom Trail on the two and half mile red brick trail, this leads you past 16 historical sites and through centuries of America's past. Starting at Boston Common, the trail winds past sites such as Massachusetts State House, Paul Revere House and the Bunker Hill Monument.

USS Constitution in Boston harbour

USS Constitution

Step on board the Boston built USS Constitution located within Boston National Historical Park, this military attraction offers an onsite museum and free guided tours by navy personnel year round. This is also one of the attractions on the Freedom Trail that you'll pass.

a close up of a brick building

Beacon Hill

Explore the cobblestones of colonial Boston in Beacon Hill. In this historic neighbourhood, you'll find grand townhouses, antique shops and chic boutiques. Head to Beacon Street to see stunning patrician mansions and the magnificent State House.

Presidential Library Museum

University's and museums

Explore some of the world’s most famous centres of excellence: both the Massachusetts Institute of Technology (MIT) and Harvard University are located just outside the city – both contain world-class museums, including the Peabody Museum of Archaeology in Harvard, one of the oldest of its kind.

a sign on the side of a building

Boston Tea Party Ships and Museums

Step back in time when visiting the Boston Tea Party Ships and Museums as you take a fully guided tour of the ships and museum. You Colonial host will take you through the history leading up until the American Revolution.

Boston Common

Boston Common

Explore the oldest park in the USA, enjoy outdoor concerts, games and numerous free events. The park originally was used as a grazing ground for cattle, it also became a training field for the military and it also has had famous speakers such as Reverend Martin Luther King Jr.

a woman smiling for the camera

"For the best sunset views in Boston, head up to the observation deck at the top of the Marriott’s Custom House. It’s a real hidden gem – some of the locals don’t even realise it’s there."

Direct Marketing Campaign Manager
Rachel, Destination Executive

"Sports fans should take a tour of Fenway Park, the home of the Boston Red Sox baseball team. Learn about the stadium’s history, visit the away team’s locker room and sit in the Green Monster: the most sought after seats in the park."

Destination Executive

Boston Harborfest

Boston Harborfest sees events all over the city spanning over the first week of July to celebrate the 4th of July each year. You can expect an impressive opening ceremony, local artists selling their works, live music, a flag raising ceremony and the beloved Parade of Lights, finished off with a spectacular fireworks display. 

Boston Wine Festival

Between the months of January and March, the Boston Harbour Hotel at Rowes Wharf plays host to a range of seminars, intimate maker-hosted dinners, brunches and reception that showcase wines from some of the world’s best wineries. The hotel’s chef, Daniel Bruce, passionately and expertly pairs the wines with incredible food. It’s a luxurious and delectable experience.  

Boston Local Food Festival

Held at the Rose Kennedy Greenway, the Boston Local Food Festival is all about delicious food made from locally sourced ingredients. Vendors from across the New England area fill the Greenway with their tasty produce ready for sampling, from spicy condiments and fruit smoothies to full meals. There’s also a Family Fun area, with entertainment throughout the day, as well as some great cooking demonstrations. 

Boston Tea Party Reenactment

Every year on the 16th of December, the Boston Tea Party comes to life, dramatised by reenactors from across New England. Locals and visitors watch on as Samuel Adams, Paul Revere, and John Hancock debate the tea tax at the Old South Meeting House, before marching down the streets to Griffin’s Wharf, where they climb aboard the restored tea ships and throw tea out into the water below. It’s a great chance to honour and learn about this important event that sparked the American Revolution.

Boston Cream Pie

This iconic desert is a must-try on any Boston holiday. More of a cake than a pie, it’s made from vanilla sponge cake that is filled with either custard or cream and finished with a chocolate glaze. If you prefer something a bit different, you can also get doughnuts based on the Boston Cream Pie across the city, similarly filled with vanilla custard and topped with chocolate. 

Baked Beans

Boston is fondly known by many as Beantown and Boston Baked Beans are the reason. Traditionally cooked slowly, sweetened with molasses and flavoured with bacon or salt-cured pork, this dish is still popular across the city and the rest of New England. 

Clam Chowder

You can expect to find this delicious creamy dish in many of the city’s eateries. Made with either milk or cream, the soup usually includes clams, pork, potatoes and onion. There are several variations of clam chowder across America, but Boston Clam Chowder can be identified by the classic thick and creamy broth. 


This Italian treat consists of fried pastry dough shells filled with a sweet and creamy ricotta filling. There’s a lot of debate over which Italian cafe serves the best Cannoli, so head to North End, Boston’s Little Italy, and sample as many as you can. 

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