Whatever you love, you are

1. Island hopping, New England style

Boston Harbour now provides a spectacular scenic backdrop to the city, and its 34 islands provide an exciting urban-adventure destination for day-trippers and city-scapers. If you are sailing your own boat, your options are unlimited. The islands are your oyster. Otherwise, it’s easy to get out to Georges Island or Spectacle Island by taking the Harbor Express ferry from Long Wharf. Either of these can serve as a launching pad to visiting the other islands – and they are also destinations in their own right.

2. Tossing a disc, riding a bike or catching some rays

We can thank Frederick Law Olmsted for transforming the marshy, mucky Charles River Basin into Boston’s favourite urban greenscape. It is an enticing and easy escape from the city, a delightful oasis that is always abuzz with hikers and bikers, runners and sunners, picnickers and play-scapers. Free concerts and movies at the Hatch Memorial Shell are highlights of summer in the city. This is where Boston’s Independence Day celebration goes down.

3. Being awestruck by an amazing array of architecture

Step onto Copley Square and into the ‘Athens of America’. Boston’s most magnificent architecture is clustered around this Back Bay plaza, symbolic of the culture and learning that gave Boston its nickname in the 19th century.

4. Following in the footsteps of revolutionary heroes

Summon your inner Paul Revere and follow the red-brick road, from the Boston Common to the Bunker Hill Monument, past 16 sites where the most dramatic scenes from history played out. This walking trail is the best introduction to revolutionary Boston, tracing the locations of the events that earned this town its status as the cradle of liberty.

5. Browsing the bookstores and sampling the sidewalk scene

Harvard Square is a vibrant, exciting place to hang out: it’s a hotbed of colonial and revolutionary history. Lined with mansions that were once home to royal sympathizers, it earned the nickname Tory Row. But its proximity to the university also means that it is a well-known address for the country’s intellectual elite. There are no official stats, but Harvard Square must have one of the country’s richest selections of bookstores. Once you have your reading material, take a seat at one of Harvard Square’s many sidewalk cafés. From here you have a front-row view of the congregations of students, the performances of buskers, the bustle of the shoppers, the pleas of the homeless and the challenges between chess players.

6. Contemplating the contemporary, the controversial and the downright confusing

Boston may appear radical in its politics, but in affairs of the art, the city has long shown more conservative tastes. The 2006 unveiling of a gleaming new Institute of Contemporary Art (ICA) on the waterfront shattered this trend, establishing the city as a hub for the art of the present and the future. Contemporary art attempts to be about real social issues and uses real materials from everyday life as a means of expression; in this way, the design of the building already fulfills the mission of the ICA, ‘to become both a dynamic space for public activity and a contemplative space for experiencing the art of our time’.

7. Cheering for the olde towne team at MLB’S oldest ballpark

The oldest of the old-style baseball parks has been home to the Boston Red Sox since 1912 – that’s almost a century of baseball. Only at Fenway do long fly balls get lost in the Triangle, the furthest corner of centre field. Only Fenway has the Green Monster, the towering left-field wall that constantly alters the play of the game. And only at Fenway do fans sing along with Neil Diamond as he croons ‘Sweet Caroline’ at the bottom of the eighth inning.

8. Feasting on creatures of the sea and cuisines of the world

Boston is the home of the first Thanksgiving and of bountiful autumnal harvests. It is America’s seafood capital, famed for clam chowder and boiled lobster. And it is a rich mix of ethnic flavors from all corners of the world. Is your mouth watering yet.

9. Cheering on the runners as they cross the finish line

Patriots’ Day – officially celebrated on the third Monday in April – means more than Paul Revere’s ride and ‘the shot heard around the world’. Since 1897, Patriots’ Day has also meant the Boston Marathon. Fifteen people ran that first race (only 10 finished); these days, the Boston Marathon attracts over 20,000 participants annually.

10. Reflecting or recreating at Thoreau’s sanctuary

Thoreau took the naturalist beliefs of transcendentalism out of the realm of theory and into practice when he left the comforts of Concord and built himself a rustic cabin on the shores of the pond. His famous memoir of his time spent there, Walden, or Life in the Woods (1854), was full of praise for nature and disapproval of the stresses of civilized life – sentiments that have found an eager audience ever since. The glacial pond is now a state park, surrounded by acres of forest.