Touring Boston Without Looking Like a Tourist

Arguably the best old city in America, Boston is chock full of fun and touristy things to do. The trick is to do them without looking like a tourist. Here is a quick rundown of a few Beantown ‘must sees’ and tips for looking like a local.

Boston was founded in 1630, and the streets pretty much haven’t changed since then. Sure, they’ve paved over most of the cobblestones, but this city was designed with cows and horses in mind, not minivans and SUV’s. When visiting, do yourself a favor and stick to the subway, locally known as “the T”, which can get you pretty much anywhere you’d want to go. It may not get you there quickly (this was America’s first subway, built in the 1800’s, and likewise hasn’t improved much since) but it’s still faster than any Boston one-way street. For subway maps and other info, check out

Boston is a small city-a walker’s city. So even if the T is running obscenely slow, you can get most anywhere on foot. As you’re walking around you’re bound to notice a thick red line painted on certain sidewalks. This is the Freedom Trail, a must for any Boston tourist. Following it takes you through the old city and past numerous American Revolution landmarks-forcing even the most jaded American to swell with patriotic pride. I’ve often said that if they put Army recruitment centers at strategic points alongside the Freedom Trail, they’d never need a draft again. To avoid looking like a tourist, always walk next to the red line, never on it. This isn’t a balance beam, people. The Freedom Trail

Not up for all that walking? Maybe a Duck Tour is in your future. Climb aboard these converted WWII amphibious transports for an eighty-minute tour-by land and by sea- of the historic, modern and trendy Boston sights. Unfortunately, it’s impossible not to look like a tourist on the Duck Tours since all passengers are strongly encouraged to “quack” at people on the street. But hey, sometimes the locals are in a good mood and will even quack back. Duck Tours

Passing through the Public Gardens, many tourists enjoy taking a trip around the pond on a Swan Boat. For $2.75 per person you can board a pontoon shaped like a giant swan, and be peddled around for fifteen minutes with about twenty other people. Again, it will be blatantly obvious that you’re a tourist because no local would be caught dead on a Swan Boat, but that’s only because they’re too proud to admit how much fun it really is.

After all that walking, floating and quacking, you’ll probably be craving a bite and a beer. And, like most tourists, you’ll find yourself drawn inexorably toward that most famous of bars, Cheers-where the only person who knows your name is the guy who swipes your credit card. The food at Cheers (it’s real name is the Bull & Finch Pub) is forgettable and overpriced, and the bar looks nothing like on TV. You’re better off taking a picture in front of the sign and then patronizing a local brewpub.

One of the best places to go when you only have a few days in Boston is Faneuil (said: FAN-yool) Hall. With that perfect combination of history, food, shopping and street performers, even the most cravenly anti-tourist Bostonian comes down here several times a year. Jugglers, mimes, and musicians of every style and genre converge on this gigantic performance space any day the weather permits. Make sure to drop a dollar in their hat or guitar case if you’re watching for more than a few

In 2004, the Red Sox won the World Series after eighty-six years of blowing it at the end of the season. This is huge. No, I mean really huge. Like, “American Revolution” huge. The Freedom Trail Organization actually repainted their red line to go past Fenway Park. Okay, so I made that part up. But be forewarned, it’s been almost four years and this whole city is still coming down from an eighty-six-year contact high. Check out a home game and see for yourself what all the fuss is about. Go to for tickets.

The only way to truly appreciate a game at Fenway is to sit in the bleachers. We’ll have none of this box-seat-behind-home-plate nonsense. It’s only in the bleachers where you’ll see the true color of Red Sox fans. All the best waves start here. All the best fights start here. And you simply haven’t lived until you’ve spent three hours heckling an opposing team’s right fielder. But the best part about sitting in the bleachers at Fenway is that there are no tourists. Everybody may not know your name, but for nine innings you’ll be an official Bostonian.

Wear a Yankees hat at your own risk.