24 hours in: Boston

True to its European roots, the cityscape juxtaposes historic charm with gleaming high-rises, financial complexes with student and ethnic enclaves, and green parks with industrial ones. Recent preservation efforts, artistic and technologic innovation, and the mayor’s initiatives to compete for coolness with neighbouring cities welcome travellers to explore Boston’s impressive historical legacy and join the revival.

EARLY RISE

With fountains and flower-lined lawns against the backdrop of the skyline, North End Park is a prime spot for early morning calm. You can sun-soak on a bench under the trellises and watch the plazas come alive with students, families, merchants and vendors, the centuries-old lifeblood of the North End.

Boston Harbor was once the city’s centre of trade and a gateway for mainly Irish and Italian immigrants to establish local communities. The neighbourhood still bustles with the import and production of goods and food that fostered Boston’s Little Italy - although today the preserved and prepared family recipes go for a little more in some of the finer restaurants.

BREAKFAST

Bypass the long queues at the touristy and overrated pastry shops on Hanover Street and find Caffé Vittoria, a little further down and a block away from the Paul Revere House. The café claims to be the first of its kind in Boston and is modelled after traditional Italian eateries. You’ll find a jukebox, old photographs and a bar in the restaurant side, while the café offers brighter ambiance for a relaxed breakfast.

If you can’t grab a table outside, choose one just inside the huge windows. The cheap prices and scrumptious pastry and coffees, which consistently earn the café a place on ‘best’ lists, will weaken your knees. Any of the beverages would be a good choice, but the tiramisu is a must - it’s supposedly the tastiest in Boston.

MID-MORNING

After indulging, you can walk along the harbour through one of the many parks that make up the Rose Kennedy Greenway, a stretch of public spaces completed in 2008 above an underground highway. If you fancy a little shopping or history, go deeper into the city through Faneuil Hall Marketplace. Dubbed the ‘Cradle of Liberty’, the hall itself was host to town meetings and protests at the beginning of the American Revolution and today is part of the larger marketplace, a popular spot for souvenir-seekers. From here you can follow the Freedom Trail, a one-of-a-kind walking trail that tracks the events of the revolution for four red-brick kilometres and is one of Boston’s biggest tourist draws.

Right off the route is the Brattle Book Shop, one of the oldest used and rare bookstores in the country. Check out the sale sections for deals on out-of-print texts, postcards and other printed material. If you continue to follow the Freedom Trail, you’ll arrive at its starting point, Boston Common. The oldest park in the country, bordered by Emerson College and the Massachusetts State House, has seen frequent demonstrations and rallies by students and activist groups. You might catch a festival or public performance, lounge on the hills, or set out for to the Common’s Frog Pond for its seasonal offerings, including a spray fountain, carousel and an ice skating rink.

LUNCH

Continue exploring local culture at the Museum of Fine Arts, which opened its new Art of the Americas wing in 2010, or the SoWa Open Market, held Sundays from May to October. Vendors set up art, baked goods, vintage clothing, handmade jewellery, antique furniture, and home-grown produce in a parking lot tucked away between art studios in the South End. Try to buy your treats from markets like this one - ‘artisan’ cupcake shops like those on window-shopping tourist mecca Newbury Street are often overpriced and not very good. Boston-based ice cream chain Emack & Bolio’s is also a safe bet for their handmade and award-winning flavours and hot fudge.

A more substantial refuelling can be found within Boston’s newest culinary additions: food trucks. The scheme, which establishes permanent locations for vendors, kicked off in summer 2011, and mandates that each truck must prepare at least one healthy option. The results include multiple grilled cheese, Vietnamese and dessert trucks, among others, parked around the city on a rotating basis.

AFTERNOON

If you’re lucky, the temperature will be above freezing and you can continue your journey outdoors. Boston is a walkable city and pedestrians rule the road; avoid driving or you’ll end up cursing at every crosswalk. Some branches of the subway system, known as the T, are less than efficient, but the MBTA bus system is a decent alternative.

Wind-battered travellers may want to take a break and use public transport, then head back out for an afternoon on the Charles River Esplanade. Even in winter, runners, joggers and bikers are drawn to the path lined with frosted trees. Take a seat on one of the benches scattered along the Charles and watch the sailboats and local university crew teams on the water. You can rent kayaks and canoes and take free yoga and dance classes on the banks during the summer.

EVENING

Gear up for some grit as you stroll down nearby Harvard Avenue. The flourishing Allston neighbourhood is littered with bars, ethnic restaurants, quirky shops and student apartments, though the area is also popular with families for its affordability and location. You’ll find a number of satisfying and inexpensive eateries, but a standout is S & I to Go. The tiny Thai restaurant does a booming takeaway business and has large windows good for people-watching from one of the four or five tables inside. The food is fast and delicious, best finished with a milky, refreshing Thai iced tea. For a more elegant meal, you can always return to the North End for its abundant Italian fare.

Boston is home to terrific music venues that see national and local acts: Paradise Rock Club, Great Scott, House of Blues, Orpheum Theatre and Sculler’s Jazz Club, recently voted the city’s best, are just a few post-dinner entertainment options. If you’re feeling feisty, check out the streets surrounding Fenway Park and be sure to listen for the infamous Boston accent. You can treat yourself to a pint or three and an eager history lesson on the city and its beloved baseball team from friendly locals at a sports bar. A biting New England chill will sweep Bostonians out of the streets and into the pubs where, like the city itself, old and young mix in an amalgam of novelty, animation and authenticity.

To find out more about Boston, visit our Boston travel guide.