Bostonians like their freedom. The city’s rebellious reputation dates back to the days of its founding by a group of religious freethinkers fleeing the dictates of the English crown. A century or so later, the same flicker of freewill sparked the War for Independence and fired up a new nation. Nowadays, this nonconformist spirit manifests itself as an unwillingness to follow traffic regulations. Rule number one for the perfect day in Boston: don’t even think about driving a car around here.
Rent a bicycle from Urban Adventours and join the cavalcade of commuters cycling along the Charles River. Cruise east along the Esplanade, a green masterpiece designed by Frederick Law Olmsted. On warm days, Bostonians migrate to this popular park to sunbathe, picnic and feed waterfowl. Take a break at the Longfellow Bridge to take in a fantastic view of the Boston skyline.
Continuing west along the river, you will reach the campus of Harvard University, apparent from the many spires and steeples on the horizon. Lock up your bike so you can browse the bookshops and boutiques of bohemian Harvard Square. While you’re here, take a tour of the historic university campus: try the unofficial `Hahvahd’ Tour for laughs.
All that time on your bike has made you hungry. Have lunch at Clover Food Lab (cloverfoodlab.com), a modern fast food joint that serves amazing, fresh, local, often organic vegetarian fare. Go for a chick pea fritter and rosemary French fries, finished off with a hibiscus iced tea, and you won’t be disappointed.
Make your way back into the city centre (if you are too tired to ride, you can take your bike on the subway, known as the ‘T’). You’ll spend the afternoon following the Freedom Trail – a great introduction to revolutionary Boston.
The red-brick path starts at the Boston Common and winds its way past 16 sites that earned this town its status as the birthplace of America. Stroll along the 2.5-mile trail, which follows the course of the conflict: from the Old State House, where Redcoats killed five men during the so-called Boston Massacre; to the Old North Church, where the sexton hung two lanterns to warn that British troops would come by sea. The Freedom Trail ends at Bunker Hill, a monument to the eponymous battle.
Retrace your steps back across the Charlestown Bridge and into the North End, an Old World enclave that has hardly changed in the last century. Italian immigrants and their descendants have held court in this warren of narrow, winding streets since the 1920s. That makes it a perfect choice for dinner. Snag one of a dozen candlelit tables at Pomodoro and feast on fried calamari and seafood fra diavolo (with spicy tomato sauce). For dessert, enjoy a cannoli and a cappuccino at Caffé Vittoria. é
Walk or taxi back downtown for after-dinner drinks at the Highball Lounge (highballboston.com), Boston’s coolest, quirkiest retro bar. Pick up one of the red plastic View-Masters to browse the menu of creative cocktails, some of which are garnished with rubber duckies. Munch on tater tot nachos and challenge your companions to a game of Jenga. It’s sure to make you feel like a kid again (but even better, since there’s alcohol).