Believe it or not, sometimes you can live in a city for years before you tour it as a visitor. At least that’s what happened to me. I lived in Boston for a year after graduating from college, and then again for law school at Northeastern University. It wasn’t until after my husband and I got married and moved to Jamaica Plain that I decided to start “touring” the city. I’m glad I did, because it’s definitely been worth it — I love getting a different appreciation of sites I may have passed many times before.

Check out our curated Boston tourist itinerary, then read on for more great info on visiting Boston’s best sites!


If I had to pick just a few “must-dos” in Boston, my top picks would be going on a Boston Duck Tour, walking the Freedom Trail (with a tour guide in period garb), possibly a nighttime cemetery tour such as Ghosts & Gravestones (if your kids are old enough that they would enjoy this), and then an afternoon in our beautiful Boston Public Garden complete with a Swan Boat ride.


Depending on what time of day you start your touristy adventures, you have a ton of options for satisfying those vacation hunger pangs that come early and often. For variety to please the whole family, try food markets like Boston Public Market (Haymarket area), Hub Hall (located at North Station), Time Out Market (Fenway/Kenmore area), or Faneuil Hall Marketplace and Quincy Market. At these markets you will find great local restaurants that offer a quick, delicious meal for all.


If you will be staying within Boston proper, everything is easily walkable or a quick ride on our public subway/trolley system, which locals refer to as the “T.” Use a map of the T if you need to plan ahead or like to have something to quickly refer to. Uber and Lyft are also easily accessible in the city and surroundings.


If you walk around a lot, particularly when doing your Freedom Trail tour or visiting the Boston Public Garden, you will stumble upon so many gems. From the history this city has to offer to the beauty in the architecture and the city’s parks, your family will find your own gems to make memories.

Definitely make sure you spot Paul Revere’s grave as well as the statues of our country’s two main political party “mascots” somewhere along your travels!

Walking through the Boston Common, which is right next to the Public Garden, you will come across a beautiful gazebo for a great photo op. You’ll also find a lemonade stand to quench your thirst, plus the Earl of Sandwich for a yummy bite to eat if needed. There’s also Frog Pond, a not-so-hidden gem, which is open during the summer months for wading, which is fancy for taking your shoes off, rolling up your pants, and walking around hopefully without too much splashing. Oh, and can you find a famous set of sculptures depicting a local book called “Make Way for Ducklings”? There’s another photo op! Before you leave this area, you might also consider making an awesome playground pitstop right next to the pond.


Staying in the center of Boston can be pricey and not everyone’s cup of tea. That said, if you’ve budgeted for it and are making it part of the experience, I have a few I would recommend. Disclaimer: I have only stayed at one of these hotels overnight but have experienced either the restaurants or the conference facilities of all of them.

  • Omni Parker House: One of Boston’s oldest historic hotels is still going strong. This hotel is right in the heart of downtown Boston and is architecturally and visually stunning. Trivia: The famous and delicious Boston cream pie was invented in this hotel’s restaurant. If you don’t stay here, you might still want to visit the lobby and restaurant while you’re out and about!
  • Boston Park Plaza Hotel: This one is pet friendly, and last time I checked it still had at least one resident dog friend who likes to hang out in the lobby. If that’s not reason enough to want to stay here, it’s been recently renovated and is a stone’s throw away from the Boston Public Garden, our theater district, Back Bay, and the fun shopping and dining experiences of Newbury and Boylston Streets, which makes it super convenient. I’ve stayed here before and highly recommend it!
  • The Liberty Hotel: This hotel is newer in the hospitality industry, but the building used to house the Charles Street Jail! How fun is that? It’s been turned into a boutique hotel and is close and convenient to one of the boarding areas for the Boston Duck Tours. Trivia for the grownups in the family: The hotel’s cocktail lounge/bar used to be the jail’s drunk tank!


When it comes to Boston sports, you either love the teams or you find them to be your beloved teams’ archrivals. Either way, you can grab some great sports memorabilia and souvenirs from Boston ProShop inside North Station/TD Garden. Otherwise, you might want to visit the souvenir shop at the Omni Parker House hotel, where you can find lots of local treats and maybe your own copy of “Make Way for Ducklings”!


You will likely be doing a lot of walking this weekend, so make sure to bring a lightweight stroller if you have children age 5 or younger — they are bound to get exhausted, and this way they can rest their little feet (but when they’re walking you won’t have something bulky to drag around).

If you want to keep your spending down when it comes to snack needs, make sure to pack a light backpack with some fruit and healthy snack bars, along with a water bottle for each person.

Finally, you know how some people like to order customized family T-shirts when they go on a trip to that major amusement park in Florida? How about ordering some Boston T-shirts ahead of time so everyone can wear them while they’re here (and you don’t have to worry about anyone asking for every single T-shirt souvenir)? Check out Bookmarked Boston for some trendy options!

Try this sample itinerary for a tour of Boston’s best tourist spots!

Angie was born and raised in Panama and attended college in Massachusetts, after which she took a couple of years to work in Boston and enjoy the nightlife before attending law school. Soon after becoming an attorney, Angie got married to the love of her life. They set down roots in Jamaica Plain, where they welcomed their firstborn, Henry, in 2012. Angie now lives in Nahant with her husband and two children (little Eloisa was born in 2015) as well as their rescue Boxer dog, Hobie. Angie is passionate about public interest law and serves as the pro bono director at Veterans Legal Services, a nonprofit legal services firm serving Massachusetts military veterans. Angie is also a certified life and leadership coach and loves supporting women and mothers on their journeys in their personal and professional lives. In addition to feeling honored to be a contributing writer for Boston Moms, Angie also enjoys writing in, and translating Boston Moms articles into, Spanish — she is a firm believer in ensuring every Boston mom feels like she/they belong here!