My kind of place: Boston, a small city with a big history

The capital of Massachusetts allows, nay compels, one to engage with its proud past, even while offering up every essential holiday facility - from food to fashion to Fenway Park.

An aerial view of Fenway Park, the home of the Boston Red Sox Major League Baseball team since 1912. Michael Ivins / Boston Red Sox via Bloomberg
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Why Boston?

Boston is an uneasy fit with the brash, go-getting United States of wide freeways and gleaming skyscrapers. It belongs to an older, cosier American Dream – of handsome brownstone houses in quiet, leafy streets and chowder by the sea. There’s an attachment to the old world, dipping into the new only after careful consideration.

Boston revels in its history. The city was born in the 17th century as part of a distant British colony, and it still feels the most British of America’s cities. But it was also where the American Revolution kicked off, with protesters tipping crates of tea into the sea as an act of defiance against colonial rule. Revolutionaries such as Sam Adams and Paul Revere are, well, revered. It appeals to the Bostonian self-mythology of being salt-of-the-earth, blue-collar men of honour.

Visitors are far more likely to encounter the other side, though – a bookish, highly educated bunch soaking in the reflected glory of having some of the world’s best universities (including Harvard) on the doorstep.

It is not a city of visceral thrills, and neither does it pretend to be. Boston is about deep-soaked charm, pleasant strollability and warm, fuzzy connections to a different era. Anything cutting edge is blanketed in a furry holster – and the finer things in life are enjoyed with well-mannered appreciation rather than avaricious haste.

A comfortable bed

Nowhere feels more Old Boston than the Omni Parker House (www.omnihotels.com; 001 617 227 8600). It's the oldest continually operating hotel in the US, having been open since 1855. Since then, the gold-plated lift doors have seen all manner of big names pass through. And not just as guests – both Ho Chi Minh and Malcolm X worked there for a while. Don't expect striking modernity in the rooms – the furnishing is supposed to evoke the 19th century rather than the 21st. Executive king rooms cost from US$233 (Dh855).

If you'd prefer youthful zest, the Nine Zero (www.ninezero.com; 001 617 772 5800) has a fabulous energy about it. Free drinks and snacks arrive in the room every night, Frette zebra-print robes hang in the wardrobe and there are red-hot views of the State Capitol building. King rooms with a skyline view cost from $318 (Dh1,168).

Of the international luxury chains clustered around the Back Bay neighbourhood, the art-deco-meets-contemporary Mandarin Oriental (www.mandarinoriental.com/boston; 001 617 535 8888) is arguably most appealing – partly due to the enormous spa. Rates start at $623 (Dh2,288).

But, easily, the most memorable option in town is the Liberty (www.libertyhotel.com; 001 617 224 4000). It's a converted prison, and the entrance to the central octagon that doubles as the lobby will wow even the most jaded eyes. The converted cells are here for those who want to go for the full jailbird chic, but it's very much a social hub – choose one of the panorama suites slightly further round for river views and more peace. These cost from $857 (Dh3,147).

Find your feet

If Boston can stick a plaque on something and declare it historic, it will do. Many of the key museums and heritage attractions are strung out along the four-kilometre-long Freedom Trail (www.thefreedomtrail.org; 001 617 357 8300), which meanders through the city centre. If picking just one site to explore in depth, make it the Old South Meeting House (www.oldsouthmeetinghouse.org; 001 617 482 6439). This was where the rallying meeting before the revolution-sparking Boston Tea Party was held. The displays inside do a good job of explaining the anger over taxation without representation while giving an idea of the key characters who pushed for independence in the face of a death penalty.

The site of the Boston Massacre, the various burial grounds and otherwise only moderately interesting old buildings are far better brought to life with someone who can tell the stories associated with them. The local historian Ben Edwards (www.walkingboston.com; 001 617 670 1888) offers private three-hour guided walks for $350 (Dh1,285).

The city's largely redbrick North End has a fiercely strong Italian heritage, and it's best discovered through your stomach. Boston Food Tours (www.bostonfoodtours.com; 001 617 523 6032) runs excellent, detailed tasting trips through the district's outwardly unassuming cafes, delis, pastry shops and restaurants. The guides give a real insight into the geography of Italian food as well as the history of Boston for $57 (Dh209) per person.

There are numerous companies offering short cruises around Boston Harbor or along the Charles River. These are pretty good for a historical overview, but private charters allow for a more personalised, in-depth experience. The Charles Riverboat Company (www.charlesriverboat.com; 001 617 621 3001) leases yachts out from $950 (Dh2,487) for two hours.

Meet the locals

Fenway Park is the most atmospheric (not to mention most idiosyncratically old-style) baseball stadium in the US. Boston Red Sox (boston.redsox.mlb.com) fans tend to be rowdily fervent, and tickets can be very hard to come by. But book well in advance and you may be able to snap them up – they start at $58 (Dh213). Otherwise, butter up your hotel concierge to see if he or she can wangle you into America's quintessential ballgame experience.

Book a table

Fresh New England ingredients meet classic French techniques at L'Espalier (www.lespalier.com; 001 617 262 3023), the most regal of Boston's dress-to-impress joints. The $95 (Dh349) three-course menu includes dishes such as chicory-glazed venison loin.

O Ya (www.oyarestaurantboston.com; 001 617 654 9900) might not look like much from the outside, but it serves up spectacular sushi and sashimi dishes. It's done small-plate style, with options including Santa Barbara sea urchin with uni mousse, kuidashi gelee and tonka bean for $23 (Dh84) or Suzuki sea bass with spicy cucumber vinaigrette for $20 (Dh73).

The seafood joints along the waterfront can be very hit-and-miss – and extremely touristy. But Lineage (www.lineagerestaurant.com; 001 617 232 0065) in the Brookline neighbourhood has a real local, in-the-know feel, and exceptional standards. Ordering the $14 (Dh52) spicy lobster taco starters should be a legal requirement.

Shopper’s paradise

Boston’s a city made for mooching along shopping streets rather than sealing yourself away in malls. One of the best is Charles Street in the genteel, well-to-do Beacon Hill area. The shops flit from OTT florists, high-end delis and cutesy stationers to chocolatiers specialising in handmade truffles and intensely gift-worthy presentation. But antiques hunters will find Charles Street most enjoyable – there’s a heavy concentration of shops specialising in century-old furniture, frames and oddities.

From there, a dogleg to the right takes you into Newbury Street, the most appealing shopping artery in the Back Bay area. It starts off aiming for the big-spenders – most of Boston’s high-end international designer outlets congregate at the eastern end – then gets progressively more independent and interesting.

Many of the best boutiques – such as Lunarik and Rescue – are in twin-level brownstone buildings, and the most treasured finds often require taking a few steps down into what’s essentially a cellar.

What to avoid

The Boston Tea Party Ships and Museum (www.bostonteapartyship.com; 001 617 338 1773) is best skipped – it's too kiddified for anyone wanting to really understand the story of the Boston Tea Party. Persistent hammy acting and being rushed through the exhibits does not a good experience make.

Also, hiring a car in a highly pedestrian-focused city like Boston will only lead to parking and traffic frustration.

Don’t miss

It's a bit of a detour out of central Boston, but the city's one must-see museum is the John F Kennedy Presidential Library and Museum (www.jfklibrary.org, 001 617 514 1600). The I M Pei-designed building makes the most of its bayside setting, and the displays inside offer an utterly engrossing look at the most mythologised US president. Cleverly, much of it is guided by JFK himself – archive audio is used extensively to tell of Kennedy's career, Second World War exploits in the Solomon Islands and personal life.

It becomes both a look at a complex man – the video footage and photos from his early life add a sense of rounded personality – and a key period in world history. Admission costs $14 (Dh51).

Getting there

Emirates (www.emirates.com; 600 55 55 55) flies direct to Boston from Dubai, with returns costing from Dh5,515 in economy and Dh19,295 in business class, including taxes.