Why go now?
Boston has a prominent place in US history, plus a mix of culture, shopping and waterfront scenery. As winter descends, the Massachusetts state capital city makes a picturesque alternative to New York for a Christmas shopping break. Art lovers get an added incentive, too, with a new contemporary section at the Museum of Fine Arts (1) (001 617 267 9300; mfa.org). If you plan a New Year visit, a new wing opens at the Isabella Stewart Gardner Museum (2) (001 617 566 1401; gardnermuseum.org, 11am-5pm Tues-Sun, $12/£8 or free to anyone named Isabella) on 19 Jan.
American Airlines (0844 499 7300; americanairlines.co.uk), British Airways (0844 493 0787; ba.com), Virgin Atlantic (0844 209 7310; virgin-atlantic.com), and Delta (0871 22 11 222; delta.com) fly from Heathrow. Icelandair (0844 811 1190; icelandair.co.uk) flies from Manchester and Glasgow via Reykjavik.
Logan International Airport is located across the harbour from Downtown Boston. The Silver Line "rapid" bus route SL1 runs from the airport terminals to South Station (3) via the Waterfront for $2 (£1.35). For other locations, the city's excellent "T" subway network can be accessed on a free shuttle bus to Airport station (4) for the blue line to Government Center (5) in Downtown. Or take a commuter ferry (001 617 222 6999; mbta.com, 6.30am-10pm weekdays, reduced weekend hours, $10/£6.65) from the airport's Logan Dock to Long Wharf ferry terminal (6).
Get your bearings
The city is bordered by the Charles River in the north and the harbour in the east, facing the Atlantic Ocean. Founded by Puritans in 1630, Boston's historic districts of the Italian North End and swanky Beacon Hill, with its cobbled streets and colonial Georgian houses, sit cheek by jowl with the gleaming high rises of the financial district to the south. Further west are the brownstone buildings of Back Bay and Fenway, both later additions constructed on reclaimed land, while Harvard University lies across the river in Cambridge.
"Charlie" smartcards discount single fares to $1.70 (£1.15) on the subway or $1.25 on the bus. A one-day travelcard covering the underground system and local buses costs $9.
The newly renovated Boston Common Visitor Centre (7) (001 888 733 2678; bostonusa.com, 9am-5pm daily) is at 148 Tremont Street on the edge of the common.
I travelled with Travelbag (0871 703 4240; travelbag.co.uk); it sells a £499 package including flights from Heathrow on American and a three-night stay at the Nine Zero (8) boutique hotel at 90 Tremont Street (001 617 772 5800; ninezero.com). Double rooms from $225 (£150), with wine each evening but no breakfast.
Alternatively, enjoy the results of the $20m (£13m) renovation at the Fairmont Copley Plaza (9) at 138 St James Avenue (001 617 267 5300; fairmont.com/copleyplaza) for its centenary year in 2012, as well as the Oak Bar with its carved wood ceiling and the mirrored Venetian room's concealed bar, a legacy of Prohibition. Doubles start at $245 (£163), room only.
Boston's budget accommodation is limited, but the Midtown (10) at 220 Huntington Avenue (001 800 343 1177; midtownhotel.com) is well-placed. Doubles from $89 (£59).
Take a hike
Follow the red brick road of the Freedom Trail (001 617 357 8300; thefreedomtrail.org) passing Boston's main historic sites and telling the story of the American Revolution. If you don't want to trace the whole 2.5 mile path, start at Boston Common Visitor Center (7) on Tremont Street. The oldest park in the US was settled by an eccentric Anglican vicar in 1622. Across the common is the 200-year-old gold-domed State House (11) (001 617 727 3676; www.sec.state.ma.us/trs); book ahead for a free tour, 10am-3.30pm Mon-Fri.
Heading down Park Street, the Granary Burying Ground (12) (001 617 635 4505, 10am-5pm daily) dates from the 17th century with notable graves including those of statesman John Hancock and revolutionary hero Paul Revere.
From here, take School Street to the Old South Meeting House (13) (001 617 482 6439; oldsouthmeetinghouse.org, 9.30am-5pm daily Apr-Oct, 10am-4pm daily Nov-Mar) where angry colonists planned the Boston Tea Party.
Turn east along Washington Street to the Old State House Museum (14) (001 617 720 1713; bostonhistory.org, 9am-5pm daily, to 4pm in Jan), where the Declaration of Independence was read. Finish at the imposing Faneuil Hall (15) (001 617 242 5642; 9am-5pm daily), whose colonial forum and marketplace saw some of the first protests against British rule.
Lunch on the run
Attached to Faneuil Hall, the stalls at Quincy Market (16) sell everything from lobster and oysters to clam chowder and Boston pretzels, for around $5-10 (£3.50-£6.50). Open 10am-9pm daily (11am-6pm on Sun).
The Museum of Fine Arts (1) (open 10am-4.45pm daily, to 9.45pm Wed-Fri, $22/£14.50, by donation after 4pm on Weds) is Boston's answer to the British Museum. With a new contemporary wing, it also holds collections ranging from early Olmec art and Egyptian mummies to silver designed by Paul Revere and one of the largest collections of Monet's work outside Paris. The Art of the Americas section, designed by Sir Norman Foster, opened last year.
Take in the view
On a clear day you can see across the harbour from the Skywalk at the top of the Prudential Center (17) (001 617 859 0648; prudentialcenter.com, 10am-8pm Nov-March, to 10pm April-Oct; $13/£8.50). Admire exhibitions on Boston's history, before taking in the city's only 360-degree view.
The up-and-coming area around Kenmore Square is home to Eastern Standard (18) (001 617 532 9100; easternstandardboston.com) with red leather banquettes and cocktails from $10 (£6.50), including Don's Zombie Circa 1934 ($16/£10.50), containing five different rums and absinthe – suggested maximum of two per visit.
Dining with the locals
Follow JFK's footsteps to the Union Oyster House (19) at 41 Union Street (001 617 227 2750; unionoysterhouse.com). Though his favourite lobster stew is no longer on the menu, try the seafood platter for $22.95 (£15).
The "raw bar" at Island Creek Oyster Bar (20), at 500 Commonwealth Avenue (00 1 617 532 5300; islandcreekoysterbar.com) has oysters from $1.50 (£1); mains average $25 (£16).
Sunday morning: go to church
Resting on 4,500 wooden pilings, the impressive Trinity Church (21) at 206 Clarendon Street (001 617 536 0944; trinitychurchboston.org) has been lauded by architects as one of the 10 most significant buildings in America, thanks to its "Richardsonian Romanesque" design, named for the church's architect HH Richardson who inspired the American revival of the medieval European style; religious murals cover the interior. Sunday services at 7.45am, 9am, 11.15am and 6pm.
Out to brunch
Refuel in style at Artisan, the new bistro at the Ritz Carlton Boston Common (22) (001 617 574 7176; ritzcarlton.com/boston). The menu is thoroughly indulgent, featuring Maine lobster omelette ($19/£12).
Newbury Street is as good for people watching as window shopping, with designer stores at the Boston Common end plus high street names and independent boutiques as you travel further west. Around Dartmouth Street there's a string of vintage stores such as The Closet (23) at number 175 and Second Time Around at number 176. To see how the other half live, head up Charles Street for antiques and boutiques stocking East Coast chic, as well as Beacon Hill Chocolates (24) at 91 (001 617 7251900; beaconhillchocolates.com). Most shops are open between noon and 5pm on Sundays.
Take a ride
Urban Adventours (25) at 103 Atlantic Avenue (001 800 979 3370; urbanadventours.com) offers on-request three-hour guided bike trips for $75 (£50); regular tours run May-November, $50 (£34). The three-hour ride (with only one steep hill) passes through the Italian North End with its historic Old North Church (26), along the Charles River Esplanade and past the residential South End's beautiful brownstone buildings. The 14 stops include home of the Red Sox baseball team, Fenway Park (27).
Walk in the park
Rest your bike-weary legs at the Rose Kennedy Greenway park (28), created as part of Boston's recent construction project, nicknamed the "big dig". A former multi-lane overpass slicing through the city has been buried, creating this peaceful oasis near the Harbourfront.
The icing on the cake
Soak up the atmosphere around Harvard University, the intellectual hub across the Charles River in Cambridge. Start in Harvard Square (29), four stops from central Boston on the red "T" line. There are many stores to browse, plus cafés and restaurants, and street artists.
The area's attractions include the Harvard Museum of Natural History (001 617 495 3045; hmnh.harvard.edu, 9am-5pm daily, $9/£6) or the Peabody museum (001 617 496 1027; peabody.harvard.edu, 9am-5pm daily, $9/£6), devoted to anthropology, and one of the oldest museums in the world.
Students lead regular "Classic Hahvahd" tours (001 617 674 7788; harvardtour.com, suggested donation $10/£6.70) from March, although private tours are available during the winter months.