Boston Itinerary Part 1

About two weeks ago, I was heading off to Boston for a leisurely spring break trip. My younger brother, who’s a junior in high school, had scored some flight vouchers a while back and decided to cash them in for a trip to Boston to see some colleges. So, when he asked if I wanted to tag along, how could I resist! I’ve collated our itinerary for our first two days and will be publishing Part 2 on Wednesday! (Scroll down to the bottom for outfit details!)

Day 1

Freepoint Hotel & Tatte Bakery

Our hotel was the Freepoint Hotel in Cambridge, which offered hourly shuttle rides to Harvard Square, our starting point each day. We began our morning at Tatte BakeryI cannot recommend this cafe highly enough. The food is truly a decadent mix of sweet and savory, and very Instagrammable. There are multiple locations over Boston and Cambridge, and we ended up going to more than one location on this trip. This time we got the avocado toast with a poached egg, and an almond croissant. The croissant! Definitely a favorite of mine on this trip.

Harvard and MIT

We took a look around Harvard College (very beautiful!) and then walked to Kendall Square and MIT, which is about a 30-minute stroll and worth the trek if you just want to get a feel for the area. You can also take the (Boston’s public transportation system), which is easy to navigate. I recommend purchasing a 7-day pass for the T, which runs about $22 to allow for easy access around the city.

Clover Food Lab

Kendall Square is not as bustling as Harvard Square, but my younger brother definitely enjoyed the atmosphere. We pursued MIT’s campus, which though sprawling is largely located in connecting buildings (so that student don’t have to walk during the winter!). We had lunch at Clover Food Lab, a Mediterranean fusion restaurant which was started by an MIT grad and relies on local cuisine. The menu changes daily but has many affordable and enjoyable offerings — it’s also all vegetarian in an effort to be sustainable. We got the
barbecue saigon burger and an eggplant plate, as well as a cardamom soda.

We then headed on the MIT tour. Honestly, even if you were visiting and not interested in attending the school, the tour is intriguing. I kept hoping to see Will Hunting walking the halls, solving some advanced math problem but alas, there was no Will (or Matt Damon 😉 ) to be found.

One thing to note is that MIT sits on the bank of the Charles River and is right across from Harvard Bridge, which connects to Boston. A 15-minute walk across will get you right into the city! It’s also gorgeous to see the river — a sailing regatta made the scene picturesque!

sweetgreen & J.P. Lick’s

We headed back to Harvard Square for dinner and picked up salads at one of my favorites sweetgreen. Weather inhibited our previous dinner plans, and we felt it was best to stay more in the area of our hotel. We ended the night at J.P. Lick’s, because who doesn’t love ice cream when it’s raining and cold? 😉 Black raspberry stole my heart, as did Boston!

Day 2

Caffe Nero

Friday, our second day, was pouring. I mean, really heavy rain. I absentmindedly had left all of my rain attire and shoes back in Berkeley, so the weather was really not on my side. We decided it would be the perfect museum day, but first — breakfast! We settled on Caffe Nero in the city, and we couldn’t have picked a cozier spot! Edison lights, big leather chairs, and shelves of books! We got coffee and some banana bread to start off the day.

There’s some shopping in this area, and the rain paused just long enough for us to pop into a few stores. The first U.S. Primark, what I’ve heard described as a cross between H&M and Ikea, was located in this area. We had to check it out, as the retailer hasn’t made its way to California yet! The prices are incredible, and so many options!!

Boston Commons

We also headed over to the Boston Commons and took a quick walk through the park before the rain started up again — it’s such a serene little oasis in the middle of a busy city!

Newbury Street & Boston Public Library

We headed over to Newbury Street, by far one of the cutest places in Boston. This is where all of the high-end shopping is and almost any brand you can imagine, you’ll find it here. Some standouts: Frye, Warby Parker, Alice and Olivia, Barbour, Kate Spade, J.Crew, Polo Ralph Lauren, Tory Burch, the list goes on. In this area, you’ll find the Boston Public Library, which is gorgeous to check out!

Thinking Cup

Lunchtime rolled around, and so next on the agenda were sandwiches at Thinking Cup. This has to be another one of my all-time favorites from this trip. This little cafe has incredible ambiance (think jazz and floating conversations), and I think I’m going to be dreaming about my Jamaican Jerk Turkey sandwich because wow, what flavor! Also, they have macarons, so enough said. 🙂

Museum of Fine Arts

We took the T to the Museum of Fine Arts. It’s sprawling and features pieces from Monet, Picasso, Turner, and Polluck — to name just a few. You could easily spend 2 hours there because it’s absolutely gorgeous. We certainly enjoyed ourselves, and it afforded us the perfect escape from the rain.


sweetgreen & J.P. Lick’s

We ended ougt again at sweetgreen and J.P. Lick’s (this time getting oatmeal cookie!). The weather took away some of our flexibility and though eating the same thing for two nights wasn’t part of the initial plan, sometimes when traveling, you have to take obstacles in stride!

Outfit Details:

Mock White Turtleneck (similar found here!) // KanCan jeans // Blue Coat (similar found here!) // Target Sunnyside Scarf // Taupe Booties (similar found here!) // Kate Spade Cedar Street Maise (similar found here!)

Pink Trench Coat (similar found here!) // Gray Long Sleeve // White Long Sleeve // KanCan jeans // Taupe Booties (similar found here!) // Kate Spade Cedar Street Maise (similar found here!) // Pink Umbrella

What’s your favorite place in Boston or where do you wish you could go? Comment below!



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