Thanks to the area's 50-plus colleges, Boston has a reputation for hitting the books first, goofing off second. To be sure, venerable institutions such as Symphony Hall, the Museum of Fine Arts and Faneuil Hall still anchor the city's hold on music, art and history. But in recent years, this little big town has emerged from its introverted shell to offer a livelier mix of cultural offerings, plus an exploding food scene. The Rose Fitzgerald Kennedy Greenway parkland extends from the North End to Chinatown, connecting a new frontier of glass and steel construction, known as the Seaport District, to downtown. This is also a city obsessed with sports and craft beer, meaning you're never far from a Celtics, Bruins, Patriots or Red Sox fan hoisting a pint for the home team in one of the Hub's zillion pubs. Go Boston.

Friday

2pm  1. 

Uncommonly local The classic tour begins at the 50-acre Boston Common, the nation's oldest public park and endpoint of Frederick Law Olmsted's green-space network, known as the Emerald Necklace. From here, if history's your thing, walk the 4km Freedom Trail, which wends its way through 16 Revolutionary-era sites, from the Boston Massacre site in front of the Old State House to the Paul Revere House in the traditionally Italian-American enclave of the North End to the Bunker Hill Monument in Charlestown.

Just follow the red-brick (or painted) trail as far as your legs can take you, perhaps as far as the ancient Warren Tavern, where George Washington and Paul Revere once tossed back a pint. The adjacent Public Garden is also worth a tour, with its Make Way for Ducklings sculpture (a tribute to Robert McCloskey's picture book) and the bench featured in the film Good Will Hunting (now an unofficial memorial to the late Robin Williams). In warmer months, glide in one of the garden's 19th-century swan boats; in winter, go ice-skating on the Common's Frog Pond.

4.30pm 2.

Back Bay watch From the Public Garden, stroll down Newbury Street into the heart of Back Bay. This neighbourhood was once as wet as Boston Harbour before being backfilled and built up with elegant 19th-century brownstones. Today, you’ll find the haughtier designer shops closest to the Public Garden, but increasingly funkier boutiques as you walk west towards Massachusetts Avenue.

Homegrown Newbury Comics is a mecca to music and pop culture. Drop into Rick Walker's for leather jackets, cowboy hats and vintage boots. The whimsical Fairy Shop has knickknacks devoted to unicorns, Alice in Wonderland and Tim Burton. Heading back east via Boylston Street, stop by Copley Square and pop in at the Boston Public Library's 1895 wing, the McKim Building, to gaze at its sumptuous Edwin Austin Abbey floor-to-ceiling painting series The Quest of the Holy Grail and John Singer Sargent's spectacular ceiling mural cycle Triumph of Religion. Outside the library, on Boylston between Exeter and Dartmouth streets, pause at the Boston Marathon finish line, site of the deadly 2013 bombings.

7.30 pm 3.

Southern comfort Home to the nation's largest Victorian brick rowhouse district, the South End is also the place for bold dining spots. One such down-home place full of artisanal spirit is the Gallows. Try one of their "boards", little bites arranged on a wooden slab, such as the longshoreman ($18), beet-cured salmon with pickled oysters, lemon-crème fraîche and pickles. Poutine ($14 to $18) is another favourite – crispy fries, cheese curd and gravy combo made three ways – or mains like steak frites with summer succotash ($24). Wash it down with a local brew like Jack's Abby Sunny Ridge or Pretty Things Baby Tree. For a blowout meal, try Back Bay's Clio, at the Eliot Hotel, whose offerings include five-course ($79) and nine-course ($124) tasting menus with dished like cassolette of lobster and sea urchin, or foie gras laquee with molasses candy and bee pollen.

10pm 4.

Night out At the Paradise Rock Club, next to Boston University on Commonwealth Avenue, you'll find performances by alternative and indie bands such as OK Go, Of Montreal and Paul Weller. If you're in a mellower mood, check out Wally's Cafe Jazz Club. Billie Holiday, Charlie Parker and Art Blakey once played here; these days, it's mostly students of Berklee College of Music and local jazz masters on stage, but it still swings.

Saturday

10am 5. 

Beacon Hill is famous for its brick and stone Federal, Greek Revival and Gothic buildings, and its myriad shops and cafes lining Charles Street. Begin your day at the Paramount, with a beloved breakfast menu that includes a malted Belgian waffle ($7), Texas-style French toast ($7) and a blue cheese, bacon and spinach omelette ($10).

Noon 6.

Here are three unconventional ways to get the lay of the land, and the sea. Head to Long Wharf and jump a ferry to the Boston Harbour Islands, a park encompassing 34 islands and peninsulas; one highlight is Georges Island, a 45-minute boat ride away ($17, children $10; ferries run until October 12th this year), site of the Civil War-era Fort Warren, where you can take in a vintage baseball game or concert and beer festival, and grab some refreshments at the snack bar. Boston Duck Tours ply the city (and the Charles River) in second World War-style amphibious landing vehicles and goofy costumed characters narrate your ride, which zigzags from the Museum of Science to the Prudential Center and the New England Aquarium ($35.99, children $24.99; Duck Tours run until November 29th). If a boat tour isn't your idea of a tea party, you can rent from the Hubway bike sharing system; 24-hour ($6) and 72-hour ($12) passes are payable with a credit card at stations throughout the city.

4pm 7.

Seaport and swing sets

The rapid development of Fort Point and the Seaport District means fewer artists living in its lofts but more to see and do. As you wander the Boston Harbour Walk along Fort Point Channel, and by the former brick warehouses along Congress Street, make a late afternoon refuelling stop at the Flour Bakery, or buy high-end provisions at the market/deli/cafe Bee's Knees Supply Company. Behind the hulking Boston Convention Center, the city is reinventing its outdoor spaces at Lawn on D, an innovative park with swing sets for adults, public wifi, a beer tent, food trucks, free games like bocce and corn hole, and live performances, such as fire-art and an ice maze.

7.30pm 8.

Seafood by the Sea

Pendant lights and fresh tiles accent the cavernous brick-and-rafter space of Row 34’s converted warehouse. Here, at one of the city’s best raw bars, begin with local oysters such as Moon Shoal ($3 each) from Barnstable, or Island Creek ($2.50 each) from Duxbury, and choose from two dozen beers on tap, such as Idle Hands’s Snake Eyes Farmhouse IPA, or Confluence, a dry hopped golden ale by Allagash. Main dishes include crispy oysters ($14 and $28), Ethel’s creamy lobster roll ($24) or pan-roasted bluefish with cherry tomatoes, zephyr squash and charred eggplant ($27).

11pm 9.

Down cellar

Two basement hangouts show the range of bar life along the waterfront. The quasi-French Bastille Kitchen’s underground Chalet, with its low seating, candles, a fireplace and a deer-antler chandelier, attracts a trendier crowd. Here, you can tuck into a late-night snack like brandade beignets ($15) and a glass of wine or a cocktail.

Decorated with photos of the Rat Pack set, Lucky’s Lounge creates a popular and laid-back hideaway, part dive-bar, part throwback to a 1970s-style wood-panelled rec room. The Sinatra Saturday Night (and Sinatra Brunch on Saturday and Sunday) features a live jazz band covering the best of Old Blue Eyes. Sunday

11am

10. Books and brunch

For eclectic reads and eats, stop by Back Bay’s multilevel Trident Booksellers and Cafe, with diner-style seating and an upstairs bar. Best-loved brunch favourites include lemon ricotta French toast ($11.95), buffalo Brussels sprouts ($8), and the Chamato, a BLT with Cheddar and fried chicken on rosemary focaccia ($12.95). To drink, try the Mood Enhancer’s blend of beet, spinach, carrot and apple ($4.95); they also serve beer, wine and mimosas. Afterwards, browse the bookshop stacks, including one of the best magazine racks in town.

1pm 11.

Baseball and Botticelli

Two of Boston's most beloved shrines are accessible by the quirky Green Line MBTA trolley. The Isabella Stewart Gardner Museum (admission $15) was built as a folly to house Gardner's eccentric art collection, which ranges from ancient statuary to 19th-century masters, to the faux Venetian palace's dreamy landscaped courtyard. The glassy addition, designed by Renzo Piano, has more space for temporary exhibitions and visitor events.

More than just Red Sox fans will appreciate Fenway Park's behind-the-scenes guided tour ($18, children $12), which takes visitors backstage at Major League Baseball's oldest theatre. Sit atop the famous Green Monster, then see the inside of the press box and the visiting team's clubhouse (not as luxurious as you'd think). © The New York Times