Visiting Australian, Mark Juddery explores a famously laid-back city with intellectual wattage and a revolutionary reputation.

Boston is perhaps the most laid-back of the cities on the north-east coast. In contrast with the frenetic energy of New York or Washington, DC, it often seems Bostonians have no more urgent concern than whether their beloved Red Sox will win a baseball game. (That’s very important, however.)

One of the US’s oldest cities, Boston exudes history and is especially famous for its role in the American Revolution. The harbour was the scene of the 1773 Boston Tea Party, an instigator of the Revolution. Two years later, the British invaded from the harbour, prompting silversmith Paul Revere’s “midnight ride”. Indeed, the history is so famous it can overshadow the presence of a young and energetic population. Greater Boston houses 100 colleges and universities, which make it glow with intellectual wattage.

7am

Boston’s Back Bay is a late-Victorian district transformed into a chic shopping area, centred on the boutiques and coffee houses of Newbury Street. It is also the location of a few charming (and reasonably priced) guesthouses, furnished with antiques and care. The Commonwealth Court Guest House, in a classic brownstone building, is on the corner of Newbury Street, which means you’ll wake to the sounds of cheerful breakfast crowds. Breakfast is not included in the tariff, which provides a perfect excuse to explore nearby cafes. Sadly, my favourite cafe, The Other Side Cafe, a mostly vegetarian-vegan bar, doesn’t open until 11.30am; however, with its famous selection of beers, perhaps that’s just as well.

Commonwealth Court Guest House, 284 Commonwealth Avenue, +1 617 424 1230, doubles from $US140 ($134) ; commonwealth court.com. The Other Side Cafe, 407 Newbury Street; theothersidecafe.com.

8am

Boston’s incredible history is obvious when walking through the South End, where the red-brick apartments house art studios, boutiques and eateries. I’m told South End Buttery, hidden behind the immaculate and tiny Union Park (more like a well-coiffed nature strip than a park), has the best coffee in Boston. Though 24 hours isn’t long enough to test this claim properly, the coffee is certainly very good and must rank among the most generous, being served in extra-large mugs. Though opened in 2005, it is already one of the “traditions” of Boston, known as much for its food as for the coffee. Organic oatmeal with maple syrup and roasted apples or pastries can be enjoyed in the dining area, formerly a high-class pub.

South End Buttery, 314 Shawmutt Avenue, less than $US15 for a generous breakfast and coffee;southendbuttery.com.

9am

From the 19th century to the 18th – it is a quick walk from the South End to the US’s oldest public park, the famous Boston Common. (“America’s oldest” seems to be a common description of Boston sites.) Apart from the history, this well-mowed picnic spot is unexceptional but it provides a useful starting point for seeing the rest of the city. Boston takes pride in its walking trails, notably the Freedom Trail, a four-kilometre red-brick trail leading to 16 historic sites. Starting from the visitors’ centre, follow the trail on a map, or book a place on a guided tour with historical figures such as Crispus Attucks and Mehitable Dawes. Tours finish near Faneuil Hall, an 18th-century commercial centre. From here, browse in the Faneuil Hall Marketplace, a noisy haven of shops, restaurants and street performers, highlighted by the Quincy Market Colonnade, New England’s largest food hall.

Shoppers should return to Back Bay to rummage through Filene’s Basement, the original “bargain basement” – a historic 102-year-old shop where designer clothes are still sold as remainders. There are now 26 branches in the US but this is the one that started it all.

Filene’s Basement, 497 Boylston Street, +1 617 424 5520; filenesbasement.com. Faneuil Hall Marketplace and Quincy Market, Merchant Row; faneuilhallmarketplace.com.

11am

Forget all your prejudices about guided tours. If you have only 24 hours to spare in Boston, a quick historic tour of the city is surprisingly entertaining and introduces you to highlights from splendid 17th-century structures to the hideous 1960s architecture of City Hall, voted the world’s ugliest building in several surveys and a favourite target of derision among locals. From the market, you can see the city by foot (led by witty Harvard students or, indeed, “Benjamin Franklin” himself), by trolley, by Segway, or eight-passenger limousine (a 1939 Cadillac). Perhaps the most enjoyable way to see Boston is in a 90-minute Super Duck Tour, in which an amphibious former military vehicle prowls the streets of the city before plunging dramatically into Boston Harbour and transforming into a boat.

Super Duck Tours leave from Charlestown Navy Yard, Baxter Road, $US35 adults, $US23 children; superducktours.com.

1pm

The town of Cambridge, founded in 1630, is not technically part of Boston but it’s closer to central Boston than most of the suburbs. A trip to Boston, however brief, would be incomplete without crossing Longfellow Bridge into Cambridge, less than 10 minutes away. Like its English namesake, Cambridge is a university town – in this case, the lofty Harvard University, alongside the Massachusetts Institute of Technology (MIT). Stop at Central Square and sample the counter lunch at the Miracle of Science (named for no better reason than its proximity to MIT) on Mass Avenue (short for “Massachusetts”), a noisy and welcoming bar and grill where the blackboard menu is designed to resemble the periodic table. The food, while simple, is uniformly excellent and healthier than offerings at the average Boston pub.

The Miracle of Science, 321 Massachusetts Avenue, $15 for lunch and a drink; miracleofscience.us.

2pm

After a cheese quesadilla at the Miracle of Science, take a 15-minute walk through ye olde campus (or, if you’ve had enough walking and gawking at majestic old buildings, a single subway stop) to Harvard Square, a bustling array of bookshops, cafes and restaurants. Because you might be recovering from your extra-large morning coffee, a stop at the coffee-free Tealuxe (choose from eight types of home-made chai) might be what you need to wind down before your next coffee.

Tealuxe, 0 Brattle Street, +1 617 441 0077; see tealuxe.com.

4pm

Returning to central Boston on the subway, head to North End, especially Hanover Street, where Boston’s large Italian-American population has created a district that could rival New York’s Little Italy or Melbourne’s Lygon Street. Despite the excellent choice of bistros and coffee shops, it is a rite of passage for any Boston visitor to join the crowd at Mike’s Pastry for its famous cannoli, wonderfully large and available in several flavours of smooth ricotta-cream filling. There are a few tables at Mike’s but as I am describing a perfect day rather than an unlikely one, plan to have your cannoli while standing in the crowd and chatting to other customers (just like in a real Italian cafe). Then move to one of the less crowded (but still busy) Italian cafes on the same block to enjoy a cappuccino or an espresso.

Mike’s Pastry, 300 Hanover Street, +1 617 742 3050; mikespastry.com.

6.30pm

On the shores of Boston Harbour (naturally), Boston has always been known for its seafood, especially clam chowder. (Since last year’s oil disaster in the Gulf of Mexico, the region has displaced Florida and Louisiana for many gourmets as the hub of American seafood.) Boston’s famous chowder is best enjoyed in the rustic surrounds of the Union Oyster House, America’s oldest (there’s that phrase again) continuously operated restaurant, a landmark of downtown Boston since 1826. A bowl of chowder, followed by half-a-dozen native oysters (or, if you prefer, a lobster pot, native swordfish, or the catch of the day) is a history lesson as well as a culinary experience.

The friendly vibe of Tremont Street in the South End and its array of popular restaurants might be a good alternative to seafood houses. (Book a seat at Picco for arguably the best pizza in Boston.)

Union Oyster House, 41 Union Street, +1 617 227 2750, $US20-$US50 for a two-course meal; unionoysterhouse.com.

9pm

There are plenty of ways to enjoy the evening. Return to Faneuil Hall Marketplace to see the daytime market transformed into a thriving (but family-friendly) nightspot. Or visit the Theatre District, an exciting mini-Broadway where streets are (temporarily) renamed after hit shows. Or catch a concert by the Boston Symphony, the Boston Pops or the Boston Philharmonic, if they’re not touring. A few cities have a famous orchestra but how many have three? It’s a sign of Boston’s highbrow culture, also apparent in the opera and dance scene.

If you would rather visit one of the scores of Boston pubs, you can spend the evening drinking Sam Adams, the city’s home brew. There’s the immensely popular Beantown Pub, where the food is awful but the beer is cold and the genial ambience has hardly changed in 200 years. Don’t forget that the original Cheers, the inspiration for the television series, is on the outskirts of Boston Common. While the exterior will be familiar from a decade of opening credits, the interior bears only a vague resemblance to the more famous Hollywood set. As the theme song goes, “Taking a break from all your worries sure would help a lot.” A day in Boston, however, might be just the break you need.

Beantown Pub, 100 Tremont Street, +1 617 426 0111. Cheers, 84 Beacon Street, +1 617 227 9605.

Qantas has a fare to Boston for about $2000 low-season return from Sydney and Melbourne including tax. You fly to Los Angeles (about 14hr), then on American Airlines to Boston (5hr 30min). Australians must apply for travel authorisation before departure at https://esta.cbp.dhs.gov. Alternatively, from New York you can fly to Boston (1hr, from $US99 on JetBlue), go by train (5hr, $US68 on Amtrak) or bus (5hr, $US15).