The Ultimate Weekend Guide to Boston


Though Sam and I love to hop on a plane and travel to places so exotic we can hardly find them on a map, we also like exploring cities closer to home. We’ve been talking about taking a weekend trip to Boston for years and finally decided to make it happen this summer.

Since Sam turned 30 in July, we used his milestone birthday as an excuse to plan a jam-packed weekend in the historic city. Though we knew we wouldn’t be able to see everything Boston has to offer in one weekend, we crammed in as much as we could.

We found that a weekend was the perfect amount of time to hit the highlights and get a good feel for the city—and it definitely left us wanting more!

Here is our weekend guide to Boston, Massachusetts:

Weekend Guide to Boston


 What to Do in Boston

With its vibrant history, world-class sports teams, and impressive architecture, Boston is packed with enough attractions to keep any traveler happy. Here is what you shouldn’t miss on your first trip to Boston:

Hit up a Red Sox Game at Fenway Park

Fenway Park

When we started planning our weekend trip to Boston, we knew we had to catch a Red Sox game at Fenway Park. Not only are the Red Sox one of the best baseball teams but Fenway Park is also the oldest baseball field in the MLB and an iconic building in its own right. It has housed the Red Sox since 1912!

We recommend purchasing your tickets early. Between Fenway’s small seating capacity and the Rex Sox’ massive fan base, sellout games are the norm.

We caught a midday game and went all out with greasy stadium food. Because what’s a baseball game without an overpriced, artery-clogging hot dog?

Check out the Red Sox’ schedule here.

Walk the Freedom Trail 

Paul Revere's House

For anyone interested in American history, walking the historic Freedom Trail is a must on any trip to the city. Starting in Boston Commons and ending at the Bunker Hill Monument, the 2.5 mile trail winds past 16 significant historic sites, including Paul Revere’s house and the site of the Boston Massacre.

We recommend allotting a full morning or afternoon to walking the trail so you don’t feel too rushed. If you’re visiting in summer, be sure to take a bottle of water with you.

You can find a PDF map of the trail here. Markers in the pavement denote each of the sites, so it’s not too hard to follow on a self-guided tour.

Check Out the Boston Public Library

Boston Public Library

 If you’re familiar with this blog at all, you probably know that I’m a total book nerd. So it should come as no surprise that I absolutely loved visiting the Boston Public Library.

Established in 1852, it is one of the most beautiful libraries I have visited (second only to the library at Trinity College in Dublin. I’d move there if I could). Be sure to spend some time in the beautiful reading room. I could have spent the whole weekend here, but we figured it would probably be a good idea to see a few other things as well.

Stroll Boston’s South End

Boston South End

One of Sam’s favorite parts of our weekend trip to Boston was strolling along the sidewalks and admiring the historic brownstone buildings. Our favorite area to explore was Boston’s trendy South End.

Feel Scholarly at Harvard University

Harvard Statue

Established in 1636, the Ivy League school is arguably the most prestigious in the nation, if not the world. Though we weren’t able to go inside any of the school buildings (I would have loved to see the library!), we enjoyed strolling the grounds and admiring the historic buildings.

Since we visited in July, the campus was fairly empty except for a few groups of prospective students taking tours.

Be sure to check out the Harvard Bookstore while you’re in the area.

Walk Along the Charles River Waterfront

Charles River

 We really enjoyed walking along the pedestrian path by the Charles River. The path is especially popular with joggers and cyclists.

If you’re ready for a faster-paced activity, hop on a city bike rental and go for a morning ride. Sam really wanted to rent a bike, but it didn’t work out for us on this visit.

 Meander the Boston Public Garden

Boston Public Garden

The large, well-manicured park is a great place for a walk or a picnic. It was particularly beautiful during our trip in July! Just be warned that it can get fairly crowded, especially on weekends.

If you have time, take a spin on the lake in one of the ostentatious swan boats.

We were so tired by the time we visited the Boston Public Garden that I don’t think we were able to truly enjoy it. It is definitely a place I’d like to visit again on a future trip!

Browse the Outdoor Shelves at Brattle Books

Brattle Books

Before all of our trips, I make a note of the best bookshops in our destination. While researching Boston, one bookshop kept cropping up: Brattle Books.

What most interested me about Brattle Books is that half of the bookshop is located outside!

Browsing the second-hand books at Brattle Books is a must for any book lover. It is one of my favorite bookshops we’ve visited so far in the United States.

Where to Eat in Boston

With all that walking and sightseeing, you are bound to work up an appetite. Lucky for you, Boston is full of incredible restaurants. Since we only visited for a weekend, we didn’t have time to try out nearly as many as we would have liked. But these are a few places to eat and drink in Boston that we enjoyed.

Tatte Bakery & Café


For breakfast or brunch, head to Tatte Bakery & Café. The pastries are flaky and delicious. They also serve good breakfast sandwiches. Pair it with a cup of coffee and you’ll be ready for a full morning of sightseeing!

We visited the Harvard Square location in Cambridge.

Multiple locations.

Regina Pizzeria

Regina Pizzaria

Located in Boston’s Little Italy in the North End, Regina Pizzeria serves some seriously delicious pizza. Just be prepared for a long wait. The line of people snaked halfway down the block when we visited on a Saturday night. We waited around 45 minutes to be seated. But the pizza was definitely worth the hassle.

We split a large pizza, but probably could have gotten away with ordering a medium since there was plenty leftover.

11 1/2 Thacher St, Boston, MA 02113-1539 

The Salty Pig

Salty Pig

If you’re a fan of charcuterie (or just want to feel like a hipster), head to The Salty Pig. The menu also includes pizza and pasta if you’d prefer something more substantial. We visited for lunch and enjoyed sitting at one of the outdoor tables and soaking up the sunshine.

130 Dartmouth St., Boston, MA 02116



Ready for a sweet treat? Head to FoMu for some delicious, dairy-free ice cream! Even though Sam and I eat dairy products and are something of ice cream purists, we found the coconut-based ice cream to be a yummy alternative to traditional ice cream (though I could definitely taste a slight difference). I enjoyed the cookie dough flavor, because everything is better with cookie dough.

There are several locations but we stopped at the one in South Boston.

655 Tremont St., Boston, MA 02118

Pavement Coffeehouse

Pavement Coffee

If you’re desperate for an afternoon pick-me-up, go to Pavement Coffeehouse for a caffeine fix. I don’t drink coffee, but Sam does—he’s actually kind of a hipster snob about it—and he gave Pavement Coffeehouse his stamp of approval.

Multiple locations. 

How to Get Around Boston

Many of Boston’s main attractions are within walking distance of each other. If you stay in a central location, you may be able to cover a lot of ground on foot.

Otherwise, the MBTA Subway is an affordable and efficient way to get around Boston. Individual rides cost $2.25. We purchased a CharlieCard at a kiosk in the metro station for $20. It allowed us unlimited use of the subway for 7 days.

We recommend roughly calculating how frequently you think you will use the MBTA to determine whether purchasing individual tickets or a CharlieCard will be most cost effective. Since we ended up walking a lot, we actually would have saved money by purchasing individual tickets.

Note: If you are arriving at Boston Logan Airport, you can take a free shuttle to the nearest metro station. The shuttle will connect you with the Silver Line, and from there you can take the MBTA into the city.

Uber and taxis are also available, but they will cost significantly more than public transit. We ended up taking an Uber from our hotel to the airport the morning we flew home because our flight was so early the MBTA hadn’t started running for the day. Though it was our most expensive transit of the trip, it was certainly convenient!

Where to Stay in Boston

The Boston Marriott Copley Place

Here’s the bad news. Boston is an amazing city, but it is also crazy expensive when it comes to accommodations. We were shocked at the hotel and Airbnb prices when we were planning our trip. You’d think every hotel room in the city was built out of solid gold. I read somewhere that it has the highest Airbnb prices of any city in the world. We found the cost of accommodations in Boston to be equivalent or more expensive than any other major city we have visited, including New York, Paris, and Amsterdam.

If you have a stash of hotel points, this might be a great time to use them! If not, we recommend checking hotels on so you can easily compare prices of most of the hotels in the city.

We stayed at The Boston Marriott Copley Place and had a great experience. The rooms were comfortable, the staff was friendly, and the location was ideal for our itinerary. We were able to walk to most of the attractions we wanted to visit and there was a MBTA stop not too far away.

What is on your Boston bucket list?

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A Weekend Guide to Boston


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