A Weekend Guide to Boston

By Maggie Reimherr

Derek and I recently had some friends from Georgia visit for a long weekend. They wanted a true Boston experience, and I'm not one to shy away from creating itineraries. I love lists and plans and organization...and being in charge. Therefore, I bring you this guide for a first-time weekend visit to Boston. As we continue to host friends and family members in town, Derek and I plan to publish a series of “weekend guides” sharing the most fun things we’ve done around the city with our guests.

This first weekend guide is 2 days in Boston (and Cambridge) for first time visitors. It’s packed full of fun activities, and you’ll truly get a feel for the city.

What you’ll need:

  1. Comfortable shoes

  2. Clothes that are cute enough to go out to dinner in but comfortable enough for some mild physical activity

  3. The OpenTable app on your phone

  4. 7-Day Link Pass, purchased from a kiosk at any MBTA station - $21 gets you train rides for the whole weekend. You may not be in town for 7 days, but it ends up being a better value with how much you take the train (the “T” in local lingo) around Boston.

  5. A sense of adventure

  6. A sense of humor

  7. A healthy appetite


Day 1 - Cambridge


Take the red line T up to Harvard Square. If you’re looking for breakfast like a true Bostonian (or Cambridgian), look no further than the Dunkin Donuts at the T station. Once you’ve grabbed your donuts and coffee, exit to Harvard Square. You are now in a beautiful land of academia and history.

Stroll around the Yard and take it all in. When our friends visited, I acted as the unofficial tour guide, spouting my limited knowledge of Harvard buildings and history. If you want to hear true experts, check out an official, student-led walking tour. It’s free and about an hour long.

After walking around campus, head to Harvard Square. If you have time, stop in at some of the stores, including the world’s only Curious George store. You can also get a "Hahvahd" shirt. You may not have gone to Harvard, but you can still wear the t-shirt.


You’ll need some fuel for your next activity, so I’d recommend lunch at Felipe’s Taqueria. It’s cheap, and it’s delicious. Don’t skip the churros.


After lunch, hop back on the T going south to Kendall Square. Once you’re there, walk to the Charles River Canoe and Kayak rental station on the Charles River. One of the best ways to see the city is from the water so go paddle on the river!* Be sure to bring a water bottle with you on the kayak, especially if it’s a hot day.

*Pro tip: If you want to avoid arguing with your significant other over who’s pulling the most weight on the kayak, just rent single kayaks. You’ve been warned.

After you drop off the kayak, there is, conveniently, a biergarten right next door to the rental station at Commonwealth. Have a beer or two. You’ve earned it.


(This is where the OpenTable app comes in handy. You can make dinner reservations with the click of a button and earn points for free food! I’m a sucker for rewards systems and free food.)

Make a reservation in advance at Cambridge Brewing Company, and walk on over there at dinner time. They have a ton of different beers, each of which are amazing. Their food menu is best described as upscale pub food (it’s delicious). Since you’re probably famished from kayaking, treat yo’self with an appetizer - we got the CBC Buffalo Chicken Tenders. Another selling point of this spot: they have a patio, so you can dine al fresco on a nice evening.


Walk to Central Square, where an evening of comedy awaits you. Purchase tickets ahead of time for the 8:00 pm mainstage show at Improv Boston. This show is entirely improvised and relies on audience participation. If you like attention (I do), you can volunteer to be part of the scenes.

At the show, they *may* offer you free entry to the 10:00 pm show that night. You should totally go if they do, but first, walk around the corner to Toscanini’s for some of the best ice cream in Boston. Their menu is full of strange and unique flavors. You’ll have trouble choosing just one.

Go get some shut eye. You earned it after this jam-packed day.


Day 2 - Boston

Yesterday was in beautiful Cambridge - today you’re going to mostly be in downtown. Slap on those walking shoes and don your patriotism; you’ll be walking the historic Freedom Trail. This self-guided (or paid, but it’s really not necessary) tour follows the footsteps of our founding fathers and shows you the historical parts of the city.


Breakfast is the most important meal of the day, right? Before you head out on your historic adventure, check out the South End, one of Boston’s coolest neighborhoods. For brunch, try South End Buttery or Tremont 647 (these are places you’ll want a reservation for).

All Day

Head to Boston Common, and if you want, go crazy and drop $3 on pamphlet explaining each stop on the Freedom Trail at the Boston Common Visitors Center. Otherwise, follow along by downloading the app or going to thefreedomtrail.org.

(Optional: Before heading out on the Freedom Trail, walk around the Boston Common and Boston Public Garden. You can even take a swan boat ride. Do it for the insta.)

Walking the Freedom Trail is simple: follow the red brick road. There’s a line of red bricks leading you through the city to each destination. If you want to make up your own song (“Follow the red brick road”) we won’t judge.

Some stops have paid entry ($10 at most), and it’s up to your whether it’s worth it. We popped into Faneuil Hall for a free presentation on the history of the hall (totally worth your time) and Paul Revere’s house in the North End (worth the $3.50 price of admission). Don’t waste your time at Quincy Market next to Faneuil Hall - it’s basically an outdoor mall.

Late Lunch

Along the Freedom Trail, there are 300+ restaurants, so feel free to take your pick. We love Saus near Faneuil Hall, and it’s the kind of hearty food you need on a walking day.

But if you find yourself in the North End at lunch time, you MUST get Italian food for lunch. All of the numerous restaurants are good - you won’t have trouble finding one.

If you don’t make it all the way to the North End for lunch, you should save room to stop at Modern Pastry when you get there. I ordered a lobster tail pastry. It was the size of my head and mostly cream, both delicious and horrifying all at once. If you’re looking for something a little lighter, go with the cannolis. You can’t go wrong with a cannoli.


Sometime in the afternoon, you’ll make it to Charlestown, where the USS Constitution and Bunker Hill are on the Freedom Trail. I recommend doing these two destinations backwards - go to Bunker Hill first, then the USS Constitution. There’s a dock near the ship where you can use your 7-day MBTA Link Pass to take a BOAT RIDE back to the Boston side of the river. How cool is that??! If you feel so inclined, you can also buy beer on this boat. The boat ride is only 10 minutes long, so Derek and I may have chugged our beers. Challenge accepted.

Early Evening

Your evening destinations are nice, so I’d recommend heading back to your hotel and freshening up a bit before you start the night. Once you’ve done that...

Take the green line T to Prudential Center and head to Top of the Hub, an upscale restaurant and bar that provides spectacular views of Boston. Have a few drinks and maybe an appetizer while you take in views. Get there in the early evening so you can see the city as the sun sets.


You didn’t think you’d go to Boston without getting seafood, did you? Have dinner at Atlantic Fish Company in Back Bay. Be sure you have a reservation because this place fills up (they, too, take OpenTable reservations). They have fresh seafood and delicious New England lobster rolls.

Are you exhausted yet? If not, good for you! My sweet husband compiled a great list of the best bar in each Boston neighborhood over on his company’s blog. Check out their recommendations if you’re still up for a night on the town.

Congratulations! You’ve seen some of the best parts of Boston in just 2 days. There is so much more to see, which is why we'll be rolling out more posts on what you can do with a weekend in Boston. Check back soon for our next guide!

Any Bostonians out there, we want to know - what’s your favorite “must see” when friends and family come visit? Anyone planning a trip to Boston - leave us a comment if you want more recommendations on what to do while you’re in town!


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