Boston or Virginia Beach?

Virginia Beach is built around the kind of beach Boston has to travel for. Its wide Oceanfront runs beside the boardwalk with lifeguards and surfing near the fishing pier. The bay beaches around First Landing are calm enough for toddlers, and Sandbridge has dunes and no hotel towers.

Boston's answer is Revere Beach on the Blue Line, small harbour beaches in South Boston and Dorchester, and the dunes of Crane Beach farther out. The water stays several degrees colder even at its August peak, so a swim there is a short, bracing treat rather than how you spend the day.

Both cities eat best from the sea. Boston's raw bars serve Duxbury and Wellfleet oysters, chowder and lobster rolls, while Virginia Beach has Lynnhaven oysters, blue crab cakes and she-crab soup. The real difference is everything else.

Boston adds the North End's Italian dining rooms and cannoli, dim sum in Chinatown and chef-led kitchens in Cambridge and the South End. In Virginia Beach the resort strip relies on chains and buffets, the best meals are at the dockside places by Lynnhaven Inlet, and anyone wanting more variety drives to Norfolk.

Boston is far ahead here. The Freedom Trail links the Old State House, the Old North Church and the USS Constitution, Beacon Hill and Back Bay keep whole nineteenth-century streetscapes, and the Museum of Fine Arts and the Isabella Stewart Gardner Museum would each justify a trip on their own.

Virginia Beach has one site of real weight, Cape Henry, where the colonists first landed in 1607, along with the Old Cape Henry Lighthouse and the Adam Thoroughgood House. An afternoon covers them all, and the fuller colonial story lies up the peninsula.

Neither city is for dancing until dawn, but Boston has more choice, on more nights of the year. Its Irish pubs, Fenway sports bars, South End cocktail lounges and student bars in Allston and Cambridge stay lively even midweek. Bars still close by 2am, though, and the subway stops soon after midnight.

Nightlife in Virginia Beach means the Oceanfront in summer: rooftop decks and beach bars full of vacationers and sailors, loud and casual. Out of season the strip goes quiet early, which leaves the lounges at Town Center or a drive to Norfolk.

The two are well matched outdoors, and both are flat and coastal, but the settings differ in kind. In Boston the green space is designed, from Olmsted's Emerald Necklace to the Charles River Esplanade. You can take a ferry to the Harbor Islands, go whale-watching for humpbacks at Stellwagen Bank or see the autumn foliage around Walden Pond.

Virginia Beach is wilder at its edges. First Landing has cypress swamp and maritime forest, and the empty barrier spit of Back Bay and False Cape is reached by bike or on foot. In summer you can watch dolphins from a kayak, and surfing and fishing trips are part of everyday life.

Boston has old New England towns in every direction, and the two classics need no car: Salem and Concord are both on the commuter rail. Concord and Lexington pair the first battles of the Revolution with the homes of Emerson and Thoreau, and Plymouth tells the Pilgrim story. Newport's cliff-top mansions, Providence's historic hill and the fishing towns of Rockport and Gloucester take the list well beyond history.

Virginia Beach has one superb outing, the Historic Triangle of Williamsburg, Jamestown and Yorktown, about an hour's drive away and easily worth a full day. After that the choice narrows to Norfolk's battleship and waterfront, Kitty Hawk on the Outer Banks and Richmond, and nearly all of it means driving.

Both work very well with children, in different ways. Boston has large institutions built for young visitors, including the New England Aquarium, the Museum of Science and the Children's Museum. Add the swan boats in the Public Garden and the decks of the USS Constitution, all in a compact centre you can walk.

Virginia Beach is a beach vacation first, with gentle bay water for toddlers, sea turtles and otters at the Virginia Aquarium, a water park and mini-golf. Near Williamsburg there is a large amusement park, the kind of big theme park Boston lacks. The drawbacks are summer heat and driving everywhere, where Boston's is a cold winter.

Boston is much easier. Downtown, the North End, Beacon Hill and Back Bay are best seen on foot, and the T reaches Cambridge, Fenway and the airport. A car is more nuisance than help, even if some lines are slow and service ends around midnight.

In Virginia Beach you can manage on foot only along the Oceanfront, using the boardwalk and the summer trolley on Atlantic Avenue. Sandbridge, First Landing and Town Center all mean driving through suburban sprawl, often in heavy summer traffic.

Boston has the better shopping, though neither city is worth visiting for it. The brownstones of Newbury Street hold fashion flagships, independent boutiques and galleries, Charles Street adds antiques and Harvard Square has bookshops. Clothing is also exempt from sales tax up to a set amount.

Virginia Beach offers a regional mall, chain stores at Town Center and strip centres, and among the souvenir stores the surf shops are the only ones with local roots.

Virginia Beach is the cheaper of the two, though neither is a bargain. Its rooms and beach houses are expensive in summer, especially at weekends, but they get much cheaper out of season. The beach, boardwalk and state parks cost little, and the main extra is a hire car.

Boston's hotel rooms are among the most expensive in the country all year, peaking in foliage season and around graduations, and meals and drinks cost well above the national average. The free parks and Freedom Trail help, and so does not needing taxis or a car.

Boston has far more on stage. It has a full classical season from the Boston Symphony Orchestra in Symphony Hall, famous for its acoustics, along with the Pops, the Handel and Haydn Society and Boston Ballet. The A.R.T. and the Huntington stage serious drama, and Berklee students fill the jazz rooms.

Virginia Beach offers touring rock and country acts at its outdoor amphitheatre and free summer concerts on the boardwalk stages. For opera or a symphony, visitors drive to Norfolk.

Neither city has a bathing tradition, and in both, relaxing means a hotel spa or simply a slower pace. The difference is when and where you find the calm.

In Boston it is an afternoon in the Public Garden or the Arnold Arboretum, a break from a brisk, purposeful city. Virginia Beach is restful on early mornings along the boardwalk and in the quiet months of spring and autumn, but crowded and loud in high summer.