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Wednesday, May 13th, 2009...9:50 pm

Insider’s Guide to Boston

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I have a few different groups of friends coming to Boston over the course of the summer, and since I won’t always be around to give them the guided VIP tour, I thought I’d throw some suggestions up on the blog (why not, right?) so that I can refer back to it as needed. I’m lazy like that. The nice thing about Boston is that it’s such a walkable city; if it’s nice (BIG if) all this stuff is potentially within walking distance if you map it right. And there’s always the T, which is cheaper than public transportation in most big cities.

Anyway, these suggestions are purely based on my idiosyncratic preferences; sorry if you think they suck!

*Take a Duck Tour: This is quite possibly the cheesiest, corniest, most touristy thing you can do it Boston, but I think Duck Tours are SO FUN and you get a really really good overview of the city in just 90 minutes. I’ve been on about four of these and never found them to be dull. Can’t say the same for my companions….

*Walk the Freedom Trail: I enjoy this more than most, probably because I’m a history nerd. But Boston is famous for really only one reason and that’s its role in the revolutionary war. So you’d be doing yourself a disservice to come to Boston and not check it out. You don’t have to do the whole thing (especially if it’s a hot day), but there are lots of pubs you can pop into along the way which makes it exponentially more exciting. It also takes you through Boston’s North End (were you can get amazing Italian food and get a sense of the city’s ethnic background) so you kill two birds with one stone. Near the end of the Trail you’ll find the USS Constitution at the Navy Yard in Charlestown. Again, I might have enjoyed this more than most because I’m a history nerd, but take the time to take a tour of the boat–it’s pretty cool. And it’s a real, live Navy yard with real, live sailors!

*Hang Out on the Esplanade: The Esplanade is a gorgeous stretch of park along the banks of the Charles River. If you’re active, this is a fantastic place to run, walk or bike. If you just feel like relaxing, take a book and a blanket. It’s never disgustingly crowded (unless it’s the 4th of July) and is easy walking distance from downtown.

*Check out Cambridge: OK, I’m biased, but I prefer Cambridge to Boston. It’s funkier and more interesting, plus you don’t need to care what people think of you because everyone’s either a) crazy in their own right, or b) too lost in the clouds to be paying attention to you. My personal favorite area of Cambridge is Inman Square. Since it’s not right on the T, it’s not as overrun as Harvard or Central Squares, but still has some great little pubs/restaurants/shops, and it’s only a very short walk from the Central Square T stop. I especially recommend Ole for some damn good Mexican food and Christina’s for an awesome ice cream dessert. The Druid is a fun spot for a pint when you’re all done. On your way back to the T in Central Square, swing by Green Street Grill (amazing cocktail menu at very reasonable prices) or River Gods (funky spot with good DJs) for a nightcap at two of my favorite neighborhood joints (I live right around the corner!). You might also check the schedule at the Middle East to see if there are any good shows on the calendar while you’re here.

*Walk Washington and Tremont Streets in the South End: It’s the hip section of Boston (read: where all the gay people/gentrification is) and I always mean to spend more time down here but….I’m lazy. The Beehive is a great, sophisticated (read: no sloppy college kids) nightspot. I won’t even get into all the good places to eat here–Masa, Toro, Myers + Chang, Hamersley’s–trying to pick my fave wouldn’t be fair.

*Fenway Park: if you’re into that stuff, it’s fun. If it’s not baseball season, taking a tour of the park is actually really cool (plus you avoid the crowds).

*Newbury Street: great spot for people-watching and shopping (REALLY good shopping), but I avoid it (unless I’m getting my hair done), mostly because I can’t afford it, and it’s always busy. However, one massive exception is the Trident Cafe, which has solid, cheap food, a local (ie: not touristy or snotty) crowd, and shares space with a bookstore!

*Shepard Fairey Exhibit at the ICA: I almost forgot!  This was a really, really cool show with some interesting interactive stuff as well.  As a bonus, you can walk to this place, Drink, for a VERY good cocktail when you’re done.  Ask for the Aviation.  Yummmmm.

Those are the highlights. Wow, now I want to go explore.

5 Comments

  • Saving The Cellar for yourself? 😛

  • Of course! Gotta keep some stuff on the DL….

  • Thanks for the information.
    This will definitely be helpful.
    Too bad you aren’t gonna be around–esp. to go on the cheesy tour to see “ducks.”

  • This is too informative, but I would not visit Boston until you discorver where African food is being sold … not only Italian food because I am ….

  • I’ve been to Boston once during my ’03 “big city tour.” Unfortunately, it was in November and we couldn’t take a duck tour, but did take another tour around the city. I definitely enjoyed all the history stuff. Boston was my favorite city of that tour despite the cold. I got to spend some time in Boston and Cambridge and eat a lot of good food. I’d definitely love to go back and catch a game at Fenway.