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Beguiling Boston

skyline view of boston over the water
By Sarah Rodrigues on 14th January 2026

Sarah Rodrigues embarks on a sophisticated transatlantic escape, where culture meets political history.

The year was 1908. A man whose skintight garb might have placed him, sartorially speaking, squarely in the realm of the modern day ‘middle-aged man in lycra’, jumped into the Charles River from the Harvard Bridge, bound in padlocked chains. Watched by a crowd of cheering onlookers, he freed himself in less than a minute.

It sounds like the stuff of contemporary stag party antics, but the man was celebrated escapologist Harry Houdini – and Boston has an appeal far more sophisticated than wild weekends, despite its large student population. It’s precisely this sophistication that makes the city an ideal destination for a grown-up getaway.

Boston packs a serious historical punch as the birthplace of the American Revolution - which marks its 250th anniversary this year. The city was the site of the Boston Massacre and the Boston Tea Party, as well as being home to the United States’ oldest municipal library and the country’s longest-established marathon.

The best way to get to grips with the city’s layout is to walk its Freedom Trail, which, despite covering just 2.5 miles, links 16 locations, each key to Boston’s role in America’s independence. From Boston Common, we wended our way past the State House and Park Street Church and on to Granary Burying Ground, Old South Meeting House and USS Constitution warship. Daily tours, led by costumed guides, bring each location to life. At US$17 per adult, this is one ticket well worth booking.

freedom trail sign in boston

As, of course, is a seat at Fenway Park, home of the Red Sox baseball team. After a fabulous jazz brunch at Beehive and a very satisfactory stroll around SoWa Vintage Market – a tantalising Aladdin’s Cave of pre-loved treasures that makes you wish you’d arrived with a trailer – we joined the home supporters swarming around the stadium. Built in 1912, it’s the oldest ballpark in Major League history. Once armed with branded caps, Fenway Franks (known, by any other name, as hotdogs) and huge plastic cups of beer, we took our seats and were blessed with a definitive Red Sox victory.

aerial view of fenway football stadium in boston

The ebullient mood stayed with us well into an evening. We enjoyed sophisticated Italian dining at MIDA South End, followed by speakeasy-style cocktails at Blind Duck, a darkly decadent bar on the 18th floor of Raffles. Elsewhere, at the intimate Urban Hearth, chef and owner Erin Miller’s New England-inspired menu left us all in raptures, while live music, chic decor, fabulous food and suave waitstaff made our night at Grace by Nia’s Seaport an unapologetically late one.

fish dish served on tiled table

As an eminently walkable city, it wasn’t too difficult to stroll off the excesses of our dinners, but for a little extra exertion, we booked with Paddle Boston to explore from the water. Fully briefed by our guide, we stepped gingerly into our kayaks and took to the Charles River, admiring the skyline as we paddled. As our cores reminded us the following day, it’s a deceptively strenuous activity, but one to be thoroughly recommended.

people kayaking on river in boston

Another day’s leisurely explorations took us to the Isabella Stewart Gardner Museum, a wildly eclectic, eccentric art collection curated by the eponymous heiress and passionate traveller. While its exterior isn’t much to behold, the building was constructed specifically for housing Stewart Gardner’s acquisitions. With four wings surrounding a central courtyard of foliage and fountains, the museum dazzles with its audacity – the layering of pieces, the deliberate failure to label works with details of their names and creators, and the stern direction from beyond the grave that if anything is moved or sold, the collection must be dissolved and donated immediately.

Also on the agenda was a visit to Harvard’s sprawling grounds. Here, the highlights include the Widener Library and the Gothic glamour of Memorial Hall. Afterwards, safe in the knowledge that we were impressed, rather than re-intellectualised, we jumped on the subway to Beacon Hill, perched quickly on the Good Will Hunting bench, then made our rather more prosaic way over the park to the Cheers bar. Despite the theme tune, nobody knew our names, but we took comfort in that. After all, we’d undoubtedly be hearing them screeched from every corner of the house within minutes of our return.

Sarah was a guest of meetboston.com

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