North America Sightseeing

The New England Conclusion: Best of Boston

The urban metropolis that is Boston is one of our most loved North American cities. Regardless of what time of year you visit, the city has a magic which will intoxicate and thrill you, pulling you back time and again. Although we finished our New England roadtrip here, Boston is more than worthy of being called a stand-alone city destination.

The Freedom Trail

One of the city’s must-dos is a walk of the 5.5 mile Freedom Trail. Start at Boston’s main Visitor Information Booth, located just northeast of the Boston Common for a free map or to sign up with one of the daily tours. If you are walking independently, the trail is marked by red paint or red bricks. The trail starts at the Boston Common which dates back to 1634, making it the oldest public park in the US. Take note of the Soldiers and Sailors monument and Frog Pond, which is popular year-round as a wading pond and ice rink.  The Freedom Trail winds its way around Downtown, through the North End and to Charlestown, ending at the Community College T Station.

The Boston Tea Party & Other History

Along the Freedom Trail, you will come across the Old South Meeting House. In December 1773, more than 5’000 Bostonians gathered here to decide the fate of 3 ships carrying tea from England. Outraged at the tax which had been imposed, the crowd rioted resulting in 340 crates of tea being dumped overboard. We visited the museum and boarded a replica of one of the ships involved.

Also along the route, keep a particular eye out for a circle of cobbled stones on a small traffic island at the junction of State and Congress Streets. This marks the spot of the 1770 Boston Massacre, where 5 men died. British soldiers fired into a group of locals that were jeering and throwing snowballs at them.

In the North End, in a cobbled square is the Paul Revere House. Paul Revere is famous in American history for his historic horse ride which warned “the British are coming!” His house dates back to 1686 and is the oldest wooden house in downtown Boston. Today it is furnished much as it was then, and tours of the house are available year-round.

Boston’s Sports Teams

Every sort of top-league spectator sport is well represented and fiercely supported in Boston. The baseball team, the Red Sox are arguably the superstars; having in recent years shrugged off a long-standing ‘curse’ of lost games. As it happens, our road trip coincided with a monumental win of the World Series Championships. Soaking up the electric atmosphere was nothing short of amazing, even for tourists with no particular affiliation to the team. If you can’t attend a game, we highly recommend you take a tour of Fenway Park so you can see the passion and feel the love the Bostonians have for the game and their team.

The local American Football team are also on the rise to fame; New England Patriots are 3-time winners of the Superbowl. The Gillette Stadium is 50kms south of Boston so its a bit of a trek to get down there. As an alternative, head to the Banknorth Garden Stadium where there are year-round games of either ice hockey or basketball. Tickets are reasonably priced and usually available on the night. We managed to attend an exhilarating ice hockey game where the Bruins won in the final seconds, totally awesome!


As you can imagine, a city as established as Boston has more than it’s fair share of shopping to keep you busy. Our favourite mall was at Copley Place and the Prudential Centre, which have key department stores including Saks Fifth Avenue and Nieman-Marcus, as well as a range of other upscale stores and high street brands. In the downtown area, don’t miss the historic Faneuil Hall and Quincy Market, which hosts an eclectic mix of speciality stores and food outlets in the restored buildings. Back Bay is home to the famous Newbury Street, which has a range of couture stores with unique offerings.

Where to Eat & Drink

For a bit of a treat, head up the Prudential tower for sundowners at Top of the Hub. Although expensive, the view over the city as night creeps in is pretty special. Boston’s little Italy has a wide range of cafes and restaurants which is buzzing with locals and visitors alike, offering delicious food and perfectly crafted coffee. We loved Caffe Vittoria for its quirky décor and the collection of antique espresso machines. My personal favourite when in Boston is Santarpio’s Pizza in East Boston. Although a little out of the way, this authentic hole-in-the-wall makes THE best pizza. There is almost always a queue for a table but its worth the wait. Italian roots, no frills and payment is cash only. So delicious!

For a local thirst-quencher, try a Sam Adams ale. The Founding Father was a brew master, so it can be no surprise that a micro-brewery adopted his name, although popularity of the ales gained momentum and it can definitely not be described as a microbrewery any more!


Although not technically part of Boston city, no trip to Boston would be complete without a detour to Harvard. Founded in 1636, this revered institution is America’s oldest university and arguably one of the best. Whether you are interested in the architecture, the museums of just the ambience in general, you need to set aside at least a day. So you don’t miss anything, we suggest tagging along with one of the student-led tours of the campus. These seasonal tours leave from the Harvard University Information Centre. Alternatively, join the Unofficial Harvard Tour which runs daily, leaving from Harvard Square.

The Peabody museum and the Harvard Museum of Natural History are especially impressive. The Widener Memorial Library is the third-largest library in America and the largest university library in the world. Not only is the architecture amazing, but the collection of 13+ million books include a Gutenberg Bible and a First Folio of Shakespeare. Unfortunately its closed to the general public, but if you can blag your way in, do it!


Share your top tips in and around Boston with our readers by leaving a comment. For more suggestions in the area, check out New England’s Best Towns and Cities. Enjoy!

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    Pitch Editors
    09/01/2018 at 11:14

    Read was interesting, stay in touch…

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