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An insider's guide to Boston

Guy Pierce / 16 November 2016

Guy Pierce spends a weekend exploring a city that successfully combines a respect for its rich past with an innovative outlook for present and future.

George Washington statue in Boston Public Garden
The Boston Common is some 50 acres and the first American city common ever, dating back to 1634. It is also home to The George Washington statue.

Up an at 'em!

It’s Saturday, 6am. Early morning is the best time to get the feel of a city.

I mooch around Boston’s Downtown streets with their closed stores, bars and theatres - Macy’s, the Paramount, Primark even (the first in the US).

The first delight of the day – Brattle’s, opened in 1825. It’s a bibliophile’s bonanza. In the book-yard, hundreds of random titles are priced at $1, $3 and $5. I’m three hours too early. I shall, and do, return.

A homeless guy asks for five dollars to help him get off the street. Whatever happened to ‘spare change’? Still, what’s five bucks? About £3.50, since you ask.

A block or two on and I’m standing on Boston Common, some 50 acres and the first American city common ever, dating back to 1634. The gold-leafed dome of the State Building shimmers to my right.

Nearby is Boylston Street station (Boston boasts a simple, punctual and cheap bus and train system), which claims to be the first subway station in the US. Unsurprisingly, Boston is full of American firsts.

The Freedom Trail

It's here at Boylston Street station that you can embark on the Freedom Trail, a two and a half mile walk through Boston’s history. You can walk alone or be escorted by a Revolution-garbed guide, all tricorn and knee-britches.

Close by is Beacon Hill, the des res area of sports stars, academics and politicos. You can sniff history (and money – ‘old’ and new) in the air as you tackle the steep, narrow, still-gaslit streets with flower-bedecked townhouses, a far cry from its mid- 18th-century ‘no-go’ zone as ‘Mount Whoredom’.

It’s delightful. And here, perhaps, lies Boston’s image ‘dilemma’. The city has long been perceived as sedate, a little too conscious of its past for its own good.

It’s a perception that Boston is keen to change, and with a nascent hi-tech start-up area, great nightlife (whether it’s chi-chi cocktails, historic pub or ‘Velcro-floored’ dive bar, take ID, whatever your age!), some of the best Italian restaurants west of Turin, thriving farmer’s markets and high-end shopping, it’s well on the way.

Things to do in Boston; the hub of the universe

Boston Common

I head through the Common with its statues – and graveyard - of the Revolutionary good and great to where MC History and his Duck await. It sounds like a rap ventriloquism act.

In fact, it’s the best way to see the city (old and fast-growing young), is in an amphibious craft. Bostonians take every opportunity to drily apologise for taking Boston and winning independence from us. MC is no exception.

ConDuckTor MC’s wide anecdotal knowledge of the city’s history entertains us as he both drives and steers ­- the duck takes to the River Charles, the divide between Boston and the city of Cambridge - threading tales of Boston history, from Paul Revere and his interrupted Midnight Ride to Bunker Hill and the massive-scale land reclamation on which much of the city stands.

Boston prides itself on civic restoration - with one astonishing exception. From the 50th floor Skywalk Observatory you look down, and think, for a city of some 650,000 folks it’s pretty car-free.

That’s because Boston’s ‘big dig’ has transformed the shoreline by sticking Interstate 93 below ground, to the tune of some $14.6 billion.

The 27-year project removed the old disfiguring flyovers and freeways, replaced by the Rose Kennedy Greenway, a series of linked parks and green spaces, boasting installation art, a wildlife carousel (you ride on a turtle, an owl, a lobstery sort of thing etc ) - fountains and flowered gardens.

Seafood, seafood and more seafood!

Boston means seafood, chowder and all. At the must-eat Legal Fish, I tackle baked scrod. I don’t ask what it is. I just like the name. I like what’s on the plate when it arrives, too. In scrod we trust.

The calamari, too, is the best I’ve ever eaten. I down a light, blond Harpoon ale with the meal. Boston has pioneered the revolution in craft beers and for $65 a Sip of Boston Brew Tour tour gets you to visit and sample the wares of a micro-brewery, a distillery and a cider houses.

These are run – and drunk - not by curmudgeonly old beery bearded types but by enthusiastic under-40s with a love for what they do. If there’s a crisper gin around than Short Path’s lavender infusion it’s not passed my lips.

Sport(s) are big in Boston. New England Revolution is their Major League Soccer side, with The Fort, the home fans’ end, generating 90-minutes of drum-beating songs, a crowd of around 15,000 occupying the New England Patriots’ 69,000-seater NFL stadium.

When Revolution score, Minutemen let loose a volley of musket fire. Old meets new again.

The best restaurant chains to visit in America

The Boston Red Sox

The Red Sox are Boston’s true sports joy. If you don’t have time to take yourself out to the ballgame, then enjoy a tour of their city centre Fenway Park, the oldest major league park, opened in 1912.

It’s redolent of Babe Ruth in his pomp, hot dogs and the thwack of maple on leather. It demonstrates how you can maintain older stadiums if you have the wit and the love.

Eshewing the rarefied Boston Library (first in the US, natch), the JFK Library and the brilliant Museum of Fine Arts, and even forgoing Cheers bar, it's over the Charles to Harvard, yet another blend of old and new as student-guides take a Reithian approach to the 90-minute’Hah-vard’ tours of the campus, which was founded in 1636, though not by John Harvard himself – he donated the land on which it was built.

Our guide Ben Kelly will be either President or the first man on Mars. Quite possibly both.

At Logan International, I ask for two farewell pints of Sam Adams ale.

‘That’ll be $17.76.’

Of course.

The writer flew with Saga Holidays partner Norwegian Air International (, which flies to Boston from Gatwick, from £149 one way/£271 return, inc taxes and charges. He was a guest of the Massachusetts Office of Travel and Tourism. Visit

The opinions expressed are those of the author and are not held by Saga unless specifically stated.

The material is for general information only and does not constitute investment, tax, legal, medical or other form of advice. You should not rely on this information to make (or refrain from making) any decisions. Always obtain independent, professional advice for your own particular situation.