Some people call me the hostess with the mostest. Well actually, no one calls me that, but I like to think that my guests do. So maybe I am a sucker for putting out a nice bowl of chips or decorating for a birthday or coming up with fun things to do more than the average person, so what! 

This past week I had my twin and one of our best friends come and stay with me in Beantown for a few days. So, naturally, weeks before their arrival I started coming up with an “Itinerary of Opportunities.” 

I wanted to make sure that we covered as much ground as possible within the three days that they would be with me, and let me tell you...covering ground was not an issue. We walked a half marathon in just one day alone! 

Between Sunday and Wednesday, lots of activities were done and lots of food was consumed. Let me break it down by detailing how our days were spent and what treats we ate. In my opinion, this little travel guide will work for anyone, and there is definitely MUCH more to do if you have some more time to kill. 

SUNDAY

Red Sox Game + Fenway Park 

One word: Sox. If you are in Boston during the spring / summer and DON’T go to a Red Sox game, you are not doing it right. I understand that many of you may have a strong dislike toward Boston sports teams, and that is totally fine. My sister hates them. No secret there. But she had an amazing time at the game because Fenway Park is so incredible in itself. With that being said, if you are visiting during a time that is not baseball season, I would still recommend going to walk around Fenway and checking out the big Sox store and all the little bars and restaurants around it. The whole area has a really cool, historic vibe that I can’t really put into words. We ate sausage and peppers, as one does at a baseball game. We spent 5 bucks on a bottle of water, as one does at a baseball game. Oh, and did I mention we were on the JUMBOTRON?!

Eats and Eateries 

• Little Miss Cupcape 

  • Custom-made birthday cake for my sister 

• Fenway Park 

  • Sausages with peppahs and onions! 

MONDAY

Charles River + Cambridge + Newbury Street 

After picking up our friend from the train, we walked back down Newbury Street which is basically the main shopping street in Boston. You want it? That street’s got it. Then we spent the afternoon exploring Cambridge, despite not necessarily having a concrete destination I wanted to show my guests. I live on the other side of the river, so walking down the Esplanade past all the boaters and runners and bikers was gorgeous. We then walked across the Harvard Bridge which is plain old LOVELY in the sunshine and it took us right into Cambridge. Fun fact, there was a guy who went to MIT in the 50s who while pledging his frat had to measure out the length of the bridge in his own measurement. Yeah, that means he had to lay down however many times all the way across the bridge. The measurement is called Smoot! Once over the bridge, we walked through MIT and a little bit of Harvard, just because why not and then eventually made our way all the way through Cambridge, back over the bridge and back home safe and sound.

Did I mention that we ended up walking a HALF MARATHON that day? Yeah. We certainly walked up an appetite, which is good because where we went for dinner certainly did not disappoint. Before I get to dinner, let me just say that before our Cambridge Excursion, we enjoyed (and inhaled) a Chocolate Challah from Japonaise Bakery and Cafe.  Unfortunately we ate it so fast we didn’t take a picture. This time, the phone didn’t eat first.

Now onto the next course. For dinner, we went to Joe’s American Bar & Grill on Newbury and the service, the brussel sprouts and the vibes were IMMACULATE. 10/10 would recommend. 

Eats and Eateries 

• Japonaise Bakery and Cafe 

  • Chocolate Challah 

• Joe’s on Newbury 

  • Ginger Lemonade 

  • Local Beer Flight 

  • Crispy Brussel Sprouts

  • Chili-Lime Grilled Chicken Salad

  • Caesar Salad 

  • French Onion Soup 

  • Barbecue Baby Back Ribs 

TUESDAY

Coolidge Corner + Faneuil Hall + The North End 

This day, this day was a good day. Why, you may ask? Because today was the day that we explored Boston, Italy and Spain ALL IN THE SAME DAY. 

In the morning I took my guests to Coolidge Corner, which is a cool(idge) neighborhood in Brookline. See what I did there? We went to one of my favorite bookstores called the Brookline Booksmith which is my go-to for fun gifts, cards, bargain books and more. Oh, it’s also my go-to for dachshund clip chips, which I picked up for my dad’s birthday. It’s a quiet neighborhood that doesn’t make you feel like you are in the city and with all the stores and places to eat, I would definitely recommend checking out COOLidge Corner. Thrift stores, a cinema, a general store, a Trader Joe’s, I mean the options are really endless. 

I was able to check off both the history and the food boxes with our next two stops, Faneuil Hall and The North End. Basically (according to Google) Faneuil Hall was a marketplace and meeting place for the Patriots leading up to the American Revolution. That’s right, we ate our lunch at the same place the Boston Tea Party was planned. Quincy Market has a bunch of different food vendors ranging from Greek food to smoothies to sushi to frozen yogurt and outside of it there are tons of shopping stores like Urban Outfitters, a Boston store, The Black Dog, Crocs and more. 

We grabbed lunch at Quincy Market and then, as if we weren’t full enough, we walked on over to The North End. Basically, it is Boston’s version of Little Italy so it has no shortage of incredible goodies to eat. It is also home to the famous Freedom Trail and Paul Revere’s home. Pre-COVID, I went and took a tour of his home and it was so awesome. I am someone who loves being inside old homes and seeing how people lived, so if you also like to do that, that is something I would recommend. If you don’t know who Paul Revere is, think THE BRITISH ARE COMING THE BRITISH ARE COMING. And if you don’t know what the Freedom Trail is, think of a 2.5 mile long brick road that passes all the essential stops that are attributed to the American Revolution. 

We went to two bakeries to get some treats: Mike’s Pastry and Bova’s Bakery. Now, while there are dozens of bakeries in this area and I can guarantee all of them sell cannolis, Mike’s is the place that is best-known for them specifically. 

After we went to Italy, we jetted home to make it to Spain for dinner. The three of us went to Spain in high school for a school trip and I decided what better way to end our girls trip than eating at Barcelona Wine Bar, where we could eat the foods we ate when we were over there years ago?! It’s a tapas place so it’s a perfect place to go to with a bunch of friends so you can share plates and things like that! When we were in Spain, we actually went everywhere BUT Barcelona, but the food is pretty much the same. The one thing I made sure to try everywhere we went was Tortilla Española, which is like an eggs and potato dish. WELL THEY HAVE IT THERE, so naturally, I had to get it. Also, if you like cheese (which I don’t but my guests do) you can order your own cheeseboards. Go wild.

Eats and Eateries:

• Quincy Market 

  • Lobster Mac and Cheese

  • Clam Chowdah

  • Lemonade 

  • Pepperoni Pizza 

• Mike’s Pastry 

  • Classic Cannoli 

  • Chocolate Cream Cannoli 

• Bova’s Bakery 

  • Raspberry and Chocolate Rugelach

  • Lemon Bowties 

  • Italian Fig Cookies

• Barcelona Wine Bar 

  • White Sangria 

  • Ginger Mocktail 

  • Kale Salad

  • Potato Tortilla 

  • Albondigas 

  • Fava Bean Hummus 

  • Ham and Cheese Croquetas 

  • Eggplant Caponata 

  • Personalized Cheese Board

WEDNESDAY

Bye Bye + Burgers + Bookstore
This was a travel day for our friend, so I kept it simple. We walked around my campus and did the whole bookstore thing to get some swag, making sure to walk down my favorite streets with insanely large houses along the way. Then we went to Tasty Burger, The Official Burger of the Boston Red Sox, before she boarded her train. And that was that!

Eats and Eateries: 

• Tasty Burger 

  • Chicken nuggets 

  • Cheeseburger 

  • Fries 

OVERALL: We walked a lot. We explored a lot. We laughed a lot. We ate a lot. We came, we saw, we conquered BOSTON. I think my guests had a pretty rockin time! And even though there is still a lot left to do, there is always next time, right?