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Why go now?
Mitt Romney, the former governor of Massachusetts, may have to resign himself to not being able to move into the White House, but he did get to enjoy the handsome State House (1) for four years from 2003 to the end of 2006. And his adopted city, Boston, is where the American Dream was born. The Massachusetts capital wears its history well. You can immerse yourself in the story of America’s 18th-century struggle for freedom from its British colonial overlords or simply indulge in the cuisine and culture on offer. And with only 45 shopping days until Christmas, the tax-free clothing on offer makes for an added attraction.
Fly in from Heathrow to Boston’s Logan airport on British Airways, its partner American Airlines, Delta or Virgin Atlantic. From here, you are spoilt for choice. A taxi will cost around $30 (£19) to most downtown hotels. Bus SL1 (“SL” is short for Silver Line) runs to South Station (2) for $2 (£1.25).
Better still, take the boat – it’s part of the city’s excellent public transport system – to Long Wharf (3). A shuttle bus will deliver you from the airport to the quayside, where the City Water Taxi ( citywatertaxi.com) skims across the water to Long Wharf for a very reasonable $10 (£6).
Get your bearings
Boston is much more European in its layout than most US cities, and crowds around its large harbour. The historic core is the North End, full of revolutionary relics – and great restaurants. To the east is the airport; to the south, the Financial District and, beyond that, the Seaport district, which is being smartened up rapidly; to the west, the serene streets of Beacon Hill. The fashionable Back Bay district, even further west, was once marshland.
America’s first subway system – known as the “T” – is the backbone of the city’s public transport. Most of the colour-coded lines use proper underground trains, while the Green Line has streetcars (trams) which run below the surface for some of their journey. The standard fare on the T and the buses is $2 (£1.25). An alternative is the Hubway, Boston’s rent-a-bike-here-leave-it-there system. You pay $5 (£3) for 24 hours’ access (or $12/£7.50 for three days) at any of 100 stations spread across the city and its surrounding area; rentals of 30 minutes or less incur no additional charge ( thehubway.com).
The main Visitor Information Bureau (4) is on Boston Common, very close to the Park Street T station (001 617 536 4100; bostonusa.com). It opens 8.30am-5pm daily (Sunday 10am-6pm). For more information on Boston, Massachusetts and the rest of the United States, see DiscoverAmerica.com.
The chain gang has been working hard to transform the former Charles Street jail into the Liberty Hotel (5) at 215 Charles Street (001 617 224 4000; libertyhotel.com). This handsome 1851 property has a breathtaking atrium (which, on weekend evenings, becomes a social hub), with cells converted into comfortable rooms. The modern adjacent tower has more space and all the usual trimmings. A night in this very comfortable slammer starts at around $500 (£313), room only.
Boston has plenty of less-expensive options and friendly smaller hotels. The Chandler Inn (6) at 26 Chandler Street (001 617 482 3450; chandlerinn.com) is in a quiet street in the South End historic district, with doubles starting from around $130 (£82), room only. The brand new suites in an annexe across the street are ideal for a longer stay.
Take a hike
The best way to immerse yourself in the past and present city is to take the Freedom Trail, which starts conveniently at the main Visitor Information Bureau (4) and is defined by a red stripe along the sidewalk for a fascinating 2.5 miles. It passes locations that were crucial to the start of the American Revolution, including the Old South Meeting House (7), the Old State House (8) (extraordinarily part-used as a T station), the merchandise-filled Faneuil Hall (9), the Paul Revere House (10) and the serene Old North Church (11). The best way to interpret the trail is in the company of a character guide from the Freedom Trail organisation (001 617 357 8300; thefreedomtrail.org), who will play out key episodes during a three-hour “Walk into History” tour; book online, $11 (£7).
Take a view
The Freedom Trail ends at the Bunker Hill Monument (12), a 221ft obelisk built to commemorate the first big battle of the American Revolution. Climb the stairs (9am-5pm daily) for a fabulous free view of the city.
Lunch on the run
Take a taxi from the monument to Cambridge – Boston’s alter ego, home to Harvard University (13). It should cost $15 (£9) to drop you off at 1246 Massachusetts Avenue, where brainy people go to meet and eat: Mr Bartley’s Burger Cottage (001 617 354 6559; mrbartley.com). Mr Bartley himself may well be perched on a chair outside, taking orders to speed up the customer turnover in the restaurant he created half a century ago. The burgers have celebrity names: the Mark Zuckerburger (with Boursin and sweet potato fries) is named for the former Harvard student who founded Facebook. Billionaire or not, you have to pay in cash: the motto is “real food, real money”.
Whether you want to buy words by the million in one of the bookstores or find a one in a million piece of art, Cambridge is a good place to shop. If you’re in the market for clothes, any garment under $175 (£110) is free of sales tax. The Garage at 36 John F Kennedy Street is full of independent stores where you can buy a lucky charm or acquire a tattoo.
The Red Line of the T from Harvard to South Station (2), followed by bus SL2 (or a tactical taxi, about $20/£12.50), transports you to the waterside at the south end of Boston’s harbour front. The Harpoon Brewery (14) at 306 Northern Avenue (001 617 574 9551; harpoonbrewery.com) produces some of America’s finest beer, with tours every half-hour at the weekend (till 5pm Sat, 3pm Sun). You learn the story of how an academic project became a successful brewery and get to taste the results.
Back in the city centre, The Bell in Hand Tavern (15) at 45 Union Street (001 617 227 2098; bellinhand.com) is the oldest tavern in the US; other tempting locations within a few doors include JFK’s favourite, the Union Oyster Bar, complete with the dedicated Kennedy Booth.
Dining with the locals
At Union Street, you are on the edge of the North End, where dozens of Italian restaurants serve anything from bargain pizzas to fine-dining masterpieces. For a feast that you are unlikely to match, aim for Taranta (16) at 210 Hanover Street (001 617 720 0052; tarantarist.com). This is where Machu Picchu fuses with the Amalfi coast, with fresh New England materials: ravioli stuffed with lobster and crab, and gnocchi made from yucca, are just the starters.
Sunday morning: go to church
“Life’s too short for long-faced religion” is the slogan of the Old South Church (17), a Gothic masterpiece on Copley Square (001 617 536 1970; oldsouth.org). The church’s “signature service” is at 11am each Sunday.
Out to brunch
After nourishing the soul, feed the body around the corner at Stephanie’s on Newbury (18), at 190 Newbury Street (001 617 236 0990; stephaniesonnewbury.com). Brunch is served every Sunday from 10am till 3pm – book in advance for “ sophisticated comfort food”.
For a very different experience, the handsome surroundings of the Oak Long Bar + Kitchen (19), in the Fairmont Copley Plaza at 138 St James Avenue (001 617 585 7222; oaklongbarkitchen.com), are just the place for clam chowder.
A walk in the park
Frederick Law Olmsted, the creator of Manhattan’s Central Park, moved on to Boston to make even more of a verdant impression. He laid the foundations for the “Emerald Necklace” of parks and waterways along the western side of Boston. Start at the Emerald Necklace Conservancy Visitor Center (20), housed in a former pumping station at 125 The Fenway in the Back Bay Fens (001 617 522 2700; emeraldnecklace.org). If it’s closed (normal hours are 9am-5pm, Monday to Friday), you’ll find a map and information boards outside.
If you wondered what the architect Renzo Piano worked on before he designed The Shard in London, it was the marvellous extension to the Isabella Stewart Gardner Museum (21) at 280 The Fenway (001 617 566 1401; gardnermuseum.org). The founder was a woman of remarkable taste, combining light and nature, art and architecture. Open 11am-5pm daily except Tuesdays (Thursdays to 9pm), admission $15 (£9).