With my family originating from around Pittsburgh and Craig’s around Boston, we’ve had a lot of experience exploring both cities. We’ve also had a lot of experiences not speaking on Sundays until the Patriots/Steelers game is forgotten, and when the Bruins beat the Penguins in the playoffs a few years ago, we had a week long stand off. Even so, Boston is a gorgeous city that offers multiple dining, shopping and tourism activities, so for Top Ten Tuesday, I bring you my favorite things to do in Boston.
1. Tour Fenway Park
Most people only get to see the famous park from the outside or have to spring for tickets. But for just $18 you can take an hour long tour through the stadium, learn the history and fun facts, and sit in the Green Monstah without paying the hundreds of dollars it usually requires. Our tour guide, Don, was so funny and informative (did you know Fenway Green is a signature color, just like Tiffany Blue?) and did a great job of making the tour entertaining for us Pirate fans (also did you know the Red Sox were playing the Pirates when they officially came up with their team name? You’re welcome). It’s a fun experience that not many people are aware is a possibility; tours run everyday, usually between 9 and 5 (check times on game days), and information can be found here on their website.
2. Shop on Newbury St
After you take a tour of Fenway, reward yourself for your great idea with a tour of Boston’s famous shopping street, Newbury. Packed with restaurants and boutiques, there’s something for everyone on the road. Be sure to stop at Tiffany’s and tell them Erin sent you…I am in the database, you know…
3. Walk Boston Commons
One of the best qualities of Beantown is the natural areas that make you forget you’re in a city. Boston Commons is a beautiful stretch of park that just happens to have an entrance right next to Tiffany’s and Chanel on Newbury! There’s always fun to be had people watching while sitting on the benches, or maybe try your hand at geocaching…there’s one there, trust me!
4. Ride the swan boats
While you’re at Boston commons, take a ride around the pond on the swan boats. It’s kind of cheesy and touristy, but the line moves quickly and then you can have a swan photobomb to treasure.
5. Visit the Boston Tea Party Museum
I’m a total nerd and love history, and Boston is the perfect place to get up close and personal with ghosts of the past. The Tea Party Museum is located near the harbor on Congress St., and you even get to throw tea overboard! Ok, I will confess I haven’t actually been here because obviously I would have a picture of me throwing tea, but I did walk by it and I will make it a stop on my next trip.

6. Eat at Faneuil Hall
Faneuil Hall is a market place institution that has some really freakin delicious food. If you have to have chowdah and lobstah rolls (I know, I’m being annoying, but do you want an accurate representation or what?) go here. And it’s near the Boston Massacre sight, so be sure to stop there on your way out!
7. Attend a Red Sox game
So I like sports, but baseball is really hard for me to follow and I’m not a crazy fan or anything. I am better, however, than the girl behind me who said “Go team, win the game”… Being inside America’s oldest ball park is very cool AND a freckle faced kid actually sells peanuts and Cracker Jacks, so when they sing “Take Me Out to the Ballgame” it’s super authentic. And Boston’s colors are very patriotic so you can break out your 4th of July outfit again.
8. Visit the Bleacher Bar
If you don’t get tickets to the game, you can still enjoy a great view of the field from inside the fun bar underneath Fenway. Obviously it fills up quickly on game days, so if you want the perfect table, plan on getting there as soon as it opens. But if you’re just strolling around Boston and need a brew and a view, this is the bar for you! (And no that rhyming wasn’t even on purpose).
9. Visit the Cheers Bar
Where everybody knows your name. Need I say more?
10. Check out Martha’s Vineyard
If you have a long weekend to fill and want to venture outside of the city, I highly recommend Martha’s Vineyard. There are ferry services that run from in or around Boston, and the ride itself is very scenic. We stayed mostly in Oak Bluffs, where this amazing pink life sized doll house was built just for me. There are restaurants, shopping, bike rentals, beaches and more, and definitely is worth the trip. A bus system is relatively easy to navigate, and allows you to explore the whole island.
No matter what you choose to do in Boston, you’re sure to enjoy yourself and learn something new.
I’m from the Boston area, gotta love Faneuil Hall! Love your blog.
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