How to spend a long weekend in Boston

Get an early start with room service breakfast and then join the three million or so visitors who trek the 2.5-mile Freedom Trail each year. With its 16 historic sites (13 are free), the trail is a walking tour through U.S. history. Many visitors do the entire length, marked by a red painted or bricked line, from the information kiosk on Boston Common to the Bunker Hill Monument in Charlestown. Others join the U.S. Park Service's free 90-minute guided tour that takes in seven of these sites. The entire trail can take a full day to compete, but four hours should get you at least to Old Ironsides in Charlestown.

Step into the elegantly simple Old State House (1713), one of the oldest public buildings in the United States, now a museum and a portal to the State Street T station. Cross over the site of the infamous Boston Massacre on your way to Faneuil Hall (1742), still used for public meetings, in the shadow of Quincy Market, once a collection of warehouses but now a beehive of upscale shops and restaurants. In past years, you'd cross under the hideously green Central Artery (part of Interstate 93) on your way to the next stop, Paul Revere's house (Boston's oldest building), but that's all gone now. In its place is a lovely park, the Rose Kennedy Greenway, now that the highway has been moved underground thanks to the multi-billion dollar "Big Dig" project, reputedly the biggest public works project in U.S. history. From here, it's on to the Old North Church (1723). One of America's most beautiful places of worship, this is where sexton Robert Newman hung the lanterns (the church still owns one of the two originals) that signaled the advance of British forces. Follow the red line to Copp's Hill Burying Ground, across from Boston's narrowest house at 44 Hull Street (known as Spite House, this 10-foot-wide structure was built in 1874 as the result of a family dispute, and you can actually rent it for a short stay if you'd prefer living in a bit of history ( "Old Ironsides," the USS Constitution, oldest (1797) commissioned warship in the world, lies at anchor below in the Charlestown Navy Yard. It's a 15-minute walk from here, but hop a cab instead. To get back to Boston proper, take the MBTA water shuttle from the Navy Yard to Long Wharf on the Boston waterfront.

Hungry? For lunch, we're off to the Union Oyster House, reputedly America's oldest continually operating restaurant, whose past habitués include Daniel Webster and John F. Kennedy. You've requested a cozy booth in the oyster bar downstairs or a window booth in the Pine Room upstairs. Although it's a bit touristy, the décor looks like it hasn't changed much in 200 years, and the oysters, lobster and other seafood selections are fresh and authentic.

Speaking of the sea, our next stop is a nautical treat so rare that many natives don't even know it exists: a boat trip out to Boston Light on Little Brewster Island (, the only remaining manned lighthouse in the U.S.

With the harbor and Boston skyline as a distant backdrop, you get to climb the lighthouse's 76 narrow winding steps and two ladders, at the top of which awaits a huge Fresnel lens, as it slowly revolves and flashes every 10 seconds. Tours, which last three hours including the trip out and back depart twice a day Friday through Sunday, from June 15 to September 30, so kudos if you planned your trip during the summer.

Dinner tonight is at one of my very favorite restaurants anywhere. I can already hear the foodies out there raising objections ("How can a restaurant with such amazing views also have good food!") but I'll stand my ground. We're headed to the Top of the Hub (, perched on the Prudential Tower's 52nd floor. True, many "view" restaurants are more view than cuisine, but this one offers both exemplary food and dazzling vistas that showcase much of what you've seen in the past three days (try to snag the room's corner table). A reasonably priced ($58) three-course prix fixe menu is one way to go (the lobster soup with coconut milk, lemongrass and ginger has been on the menu for ages, and with good reason); but everything on the a la carte menu is worthy of the scenery. The desserts here are first rate, too, but you might want to save room for one more treat.

Hop in a cab or walk across Massachusetts Avenue's Harvard Bridge to Central Square in Cambridge. Your destination is Toscanini's (, purveyors of arguably the best ice cream and sundaes in the United States, if not the known universe ("Best ice cream in the world," according to the New York Times, with apologies to Jenni's Ice Creams in Columbus, Ohio). Don't worry, the line moves quickly and the wait is worth it.

From here, it's a lovely walk across the Charles back to Boston. Or heck, you've walked enough - take a taxi.

Just ask the cabbie not to drive like a true Bostonian.


George Hobica is founder of the low-airfare listing site