Our Wicked Good Boston Bucket List: Franks, Freedom and So Much More

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Our first day in Boston was a perfectly crisp and clear Massachusetts day. We biked along the Esplanade, sipped on an incredible cappuccino at The Thinking Cup on Newbury Street (go there), watched as they constructed the Boston Marathon finish line, and saw the famous Keytar Bear playing in The Common. Needless to say it was a pretty epic day…

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Before the sun had a chance to set, we had seen more college campuses (53 in Boston alone!) than we both toured in our adolescence combined, absorbed more history than our Social Studies teachers ever could have hoped to teach our 13 year-old selves and as we biked along the glittering Charles River, we couldn’t help but think of a few more items to add to our wicked good Boston Bucket List! In no particular order here they are…

1. You can’t miss a chance to jog/walk along the Charles River and simultaneously tour BU, MIT, Cambridge and Harvard… but what’s the real gem?

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Don’t miss the chance to run through Harvard Square and rub John Harvard’s “lucky” bronze boot! The best part about this story is that back in the 90’s, tour guides began encouraging visitors to emulate a (non-existent) student “tradition” of rubbing the toe of John Harvard’s left boot for luck. So, while the statue as a whole was once darkly weathered, the left toe now gleams almost throbbingly bright! You can’t miss the chance to be a part of this un-tradition.. hey, we make our own luck right?!

2. Find the giantly historic, 60-foot Citgo sign in Kenmore Square, and while you’re at it…

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cross the bridge over to Cambridge to see the equally ginormous Shell “Spectacular” sign!:

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3. Watch the swan boats as you enjoy picnic in the Public Garden. Amazingly beautiful and romantic:

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4. This one’s a given, but we have to mention it, walk the Freedom Trail (map here)! But be sure to give yourself plenty of time so you can veer off the double brick path to discover all of the incredible tastes, sounds and sites that are bound to beckon your name. We have to confess, after 2 attempts we still never completed the 2.5 mile trail… that either shows how easily distracted we are, or how awesome Boston is… or both! We recommend a full day, just in case.

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5. You see that line below? That’s for Giacomo’s, regarded as THE BEST Italian restaurant in Boston. Famous for it’s made fresh in-house pastas and “to die for” sauces, this no-frills establishment is cash-only, takes no reservations (Back Bay location does), has no valet parking and serves no desserts (there’s Mike’s Pastry across the street for that). So what’s the big deal right!? Well it’s incredible, insanely affordable and you DON’T want to miss it. If you’re on the Freedom Trail and you time it right, you might just pass this place right when the doors open at 5, though we recommend arriving around 4pm to wait in line, there are more tips for you here.

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6. With so much left to say, but not enough time to say it all, we will end our list with a classic: watching the Red Sox play ball at Fenway Park!

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Along with that comes doing the wave in the stands!

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And a total bucket list must have, eating a Fenway Frank! They even have veggie dogs and gluten-free buns at specific concessions, everyone wins!

Be sure not to leave before singing “Sweet Caroline” in the middle of the eighth inning! A Fenway tradition at every game since 2002. Fun Fact: On opening night of the 2010 season, the song was performed by Neil Diamond himself!

We had a hard time peeling ourselves out of this incredible city, so much so that it almost seemed unfair to try and put together a list of what to do because really, YOU SHOULD DO EVERYTHING.

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