Walk the Freedom Trail around Boston, the city that gave the world John F Kennedy and Dunkin' Donuts - not to mention a certain tea party

Birthplace of the American revolution, John F Kennedy and Dunkin' Donuts, Boston has a longer and richer history than most cities in the US. It is also one of the most attractive, especially now that The Big Dig - a huge undertaking designed to re-route the once elevated section of the city's arterial motorway underground - has been finished. New houses, shops and parks are filling the spaces left, making even greener the city that already has a chain of interconnecting parks known as the Emerald Necklace.

Though Boston has a typically US skyline, thanks largely to its financial district, many of its streets and neighbourhoods feel more European and date back to the 17th century. Cobbled lanes run through the early 19th-century terraces of Beacon Hill, and North End could pass for a small Italian town. Across the Charles River is Cambridge, which, due to the presence of both Harvard University and the Massachusetts Institute of Technology (MIT), has an eclectic, cultured and slightly bohemian air.

Best hotel

For elegance and sheer opulence, Boston's best hotel has to be The Four Seasons (001 617 338 4400; www.fourseasons.com/boston) at 200 Boylston Street. Its location, in the heart of the city, next to Beacon Hill and overlooking the beautiful Boston Public Gardens, is hard to beat. And, though its featureless exterior may not win your admiration, step into the marble lobby lined with fountains and you can't help but smile at the lavishness of it all. There are even chandeliers in the lifts. Though the hotel is just 20 years old, much of its decor is in 19th-century style. All the rooms are huge. The Four Seasons doesn't do anything as mundane as "doubles" - it starts with what is termed a "moderate" room with a kingsize bed at $478 (£271) per night. It's plush but, if you want to really splash out, go for a Garden Suite overlooking the public garden - it includes a mahogany dining table that seats six, a bathroom in Italian and Asian marble, a 42in plasma-screen television and a guest powder room. Garden Suite prices begin at $3,036 (£1,723) per night. Other facilities include a heated pool with skyline views on the eighth floor.

More modest prices can be found on Harvard Square in Cambridge where The Charles Hotel has, in addition to its high level of friendly service, two main attractions - its proximity to the colleges of Harvard and MIT and a small ice rink right outside its front door. The rooms are Shaker in style with light but cosy custom-designed down quilts. Doubles start at $335 (£190) per night.

Good value for its location in Boston's Back Bay area, Hotel 140 (001 617 585 5600; www.hotel140.com) is a boutique hotel which opened in June this year at 140 Clarendon Street. Its lead-in price is $178 (£101) for a double room with continental breakfast.

Best restaurant

The Aujourd'hui at The Four Seasons (001 617 338 4400; www.fourseasons.com/boston) is a clear leader. Its spacious, oak-panelled dining room has windows looking out on to the gardens. Chef Jerome Legras devises menus that are modern French with a local twist. Dishes include crispy soft-shell crab with native corn, chanterelles and salad as an appetiser and Maine lobster Navarin with Jerusalem artichoke purée and seasonal vegetables as an entrée. Everything is cooked to perfection and, unlike some American restaurants, the atmosphere is quiet and calm. A three-course meal without wine costs around $84 (£48) per person.

At Meritage, the restaurant inside Boston Harbour Hotel (001 617 439 3995) in Rowes Wharf, Daniel Bruce designs his menu to complement the wines in the cellar - a technique he has developed through the hotel's involvement with the Boston Wine Festival. Venison, for example, goes well with a Malbec by Nicolas Catena from Angelica Vineyard. Additionally, the menu is arranged in a succession of small and large plates to go with a series of red or white wines. Small plates cost $17 (£9.65) and large plates cost $33 (£18.75) meaning that if you stick to three small plates you can have a great meal for $51 (£29).

If you feel peckish during the day, pop into Au Bon Pain on Brattle Street, Cambridge ( www.aubonpain.com), for a bagel topped with cranberries (a local speciality) or a blueberry muffin. A bagel breakfast (which includes a great cup of coffee) costs $3 (£1.70).

Best cultural attraction

Walk the city's Freedom Trail (a red-brick path in the pavements) and you'll see 16 sites where American democracy was born - they include Massachusetts State House, Paul Revere House, the Old Granary Burying Ground and Old South Meeting House (where the "tea party" began). However, you may prefer not to take the official tour which is supposedly enhanced by "spirited, costumed characters".

Not to be missed is the Museum of Fine Arts on Huntington Avenue (001 617 267 9300; www.mfa.org), which has an encyclopedic collection of more than 4,000 pieces from around the world. Here you can gaze upon the works of painters from Rembrandt and Monet to Edward Hopper.

Best shopping

Clothes are generally less expensive in the US than the UK and Boston has all the designer stores you would expect. Go to the Downtown Crossing and Waterfront districts where you'll find Macy's, Filene's, Filene's Basement and Faneuil Hall Marketplace. Filene's Basement is where you can buy designer wear at good discounts because the store operates an automatic date markdown system. If an item hasn't sold within a certain number of days, it will be marked down in stages to 25 per cent or less of its original value.

North End market has a cluster of small shops selling Italian food and drink. Cambridge is a great place to find rare vinyl records, vintage clothing and books.

Best sightseeing

For sweeping 360-degree views of Boston, go to the Prudential Center at 800 Boylston Street (001 617 859 3156; www.prudentialcenter.com), take the elevator to the 50th floor and enter the Skywalk Observatory (tickets cost $9.50 (£5.40) for adults, $6.50 (£3.70) for children under 12). You'll see all of Boston's major sights - marks on the windows show you where they are - including its many parks. On a clear day, you can see Cape Cod. The Skywalk is open from 10am to 10pm.

More quirky (or should that be quacky?) is the Boston Duck Tour (001 617 267 3825; www.bostonducktours.com) which is a guided tour around the city in a Second World War amphibious landing vehicle. The highlight is the "splashdown" as the "con-duck-tor" drives the craft into the Charles River. Tours leave from the Prudential Center and the Museum of Science. Adults pay $25 (£14) and there are concessions for children, seniors and people with special needs.

Best nightspot

Go back to the Prudential Center and up in the elevator to visit the Top of the Hub restaurant and bar, which has the distinction of being two floors above the Skywalk Observatory. You don't have to eat; instead, listen to the better than average jazz band and enjoy a cocktail while watching the planes land at Logan airport. Top of the Hub stays open until 11pm on Fridays and Saturdays.

Boston is not renowned for its night life but some restaurants in Chinatown stay open until 4am and North End comes alive with the sound of Italian music and busy Italian restaurants in the evenings. Clubbers should head for Boylston Place, a little alley in the theatre district, which is home to The Big Easy (001 617 351 7000; www.bigeasyboston.com).

How to get there

American Airlines (0845-7789 789; www.aa.com), Air France (0870-142 4343; www.airfrance.com), British Airways (0870-850 9850; www.ba.com), KLM (0870-5074 074; www.klm.com), United Airlines (0845-8444 777; www.united.com) and Virgin Atlantic (0870-380 2007; www.virgin-atlantic.com) all fly from Heathrow to Boston Logan Airport. American Airlines, Continental Airlines (0845-607 6760; www.continental.com), KLM, Northwest Airlines (0870-507 4074; www.nwa.com) and US Airways (0845- 600 3300; www.usairways.com) all fly from Gatwick. American Airlines flies from Manchester. Icelandair (0870-787 4020; www.icelandair.net) offers return flights via Reykjavik from Heathrow. Key2holidays (020-7749 6800; www.key 2holidays.com) is now offering return flights with American Airlines with a three-night stay at the Copley Square in Boston during November for £471.

From the airport you can take the subway (which is known as the T) into central Boston. Trains run every four to 13 minutes from 5.30am to 12.30am and cost $1.25 (70p). Taxis into the centre cost between $25 (£14) and $30 (£17). The T is the best way of getting around Boston - you can buy one-day, three-day and seven-day passes which entitle you to limitless journeys.

For more information contact the Massachusetts Office of Travel and Tourism ( www.mass-vacation.com).

Ian White travelled as a guest of the Massachusetts Office of Travel and Tourism and Icelandair.