Let’s get one thing straight: Boston is not New York. However, Beantown is just as worthy as the Big Apple for a grown-up getaway, sipping cocktails at rooftop bars, shopping til you drop and catching a big game.   

Centuries of history, from rebellious tea-dumping to revolutionary plots, can be found on Boston’s Freedom Trail, a 4km walk that does a stellar job of orienting you in the city. Boston’s defining blend of old world and new is on display as red brick meets sleek skyscraper. Afterwards, it’s time for a drink. Luckily, the trail ends at the sprawling green expanse of Boston Common (smaller and more sedate than Central Park) and the famous Cheers bar is nearby. Nobody actually knows my name, but a cold Sam Adams goes down a treat in classic dive-bar surroundings.

From here, it’s a couple of blocks to well-to-do Beacon Hill. This is the West Village of Boston, where chichi coffee shops and independent stores fill grand, brownstone buildings. Three floors of packed shelves at Beacon Hill Books is my kind of shopping spree, plus there’s a café for a pick-me-up. If your shopping style is more second-hand treasures than boutique designer-wear, the SoWa Vintage Market buzzes to life on Sundays in a former factory complex. Outside, it’s all about sizzling, frying and rotating street food. Inside, there’s a warren of artists’ studios where the creators themselves work away while you peruse vibrant paintings and ethereal sculptures. The basement is dedicated to a vintage market where stalls overflow with grunge-era plaid, biker jackets that smell like old smoke, and bric-a-brac galore. 

On game days at Fenway Park, it feels like everyone in Boston makes a pilgrimage to see the Red Sox play. I know nothing about baseball, but the atmosphere is electric. Mexican Waves sweep across the crowd and, at the satisfying thunk of a home-run hit, everyone is on their feet (including me). To celebrate the Red Sox win, I head to Shybird in Fenway for dangerously moreish rotisserie chicken with finger-lickingly good sauce.

Ending a typically Bostonian day, try a pint at The Dubliner bar. Basically, I want to sip a slightly sub-par stout (Guinness doesn’t travel well) in the city that brought me Dropkick Murphys. For a more sophisticated tipple, the lounge atop Raffles Hotel pours a signature Boston Sling as red as a Manhattan. It comes with a vertigo-inducing view of the city’s Back Bay neighbourhood, twinkling at night. Boston may not have the size, scale or film-backdrop familiarity of NYC, but give me Beacon Hill and SoWa Market over Fifth Avenue, a Boston Sling over a Manhattan, or game day at Fenway Park over Yankee Stadium any day. 

Visit Boston’s official tourist site.