In late October, my mom and I took a New England road trip. We hit up Kennebunkport, Newport, and 2 days in Boston. My mom and I like to travel together a few times a year and we do the coolest things. We mainly stayed in the Back Bay area of the city but we did a lot of walking, exploring and eating! Read all about what we did with our 2 days in Boston below.
2 Days in Boston: the Best Things to Do for Your Mother-Daughter Trip and our Two Day Boston Itinerary
A yummy Mexican restaurant that has a few locations in the Boston area. We feasted on hot queso dip, pork carnitas nachos, fresco guacamole, tacos, and frolita’s (their frozen margarita). When they bring you the check, they bring cotton candy to cleanse the palette. Cotton Candy is always a win in my book! I highly recommend making a reservation since they’re a popular spot and booked in advance. You’re lucky to get a seat if you drop in and you need to try it for yourself. They’re open daily from 4 p.m. to 2 a.m. The kitchen stops serving at midnight.
A small bakery chain in Boston, Tatte (like a latte) is a great spot if you need a place to hole up and work for a little while or want a low-key breakfast. The food is fantastic and we tried the breakfast sandwich, avocado tartine, and traditional shakshuka. They have several locations so you can’t give me a reason to at least not go for breakfast and coffee. It was so easy to stop in and grab something and go, we ate breakfast here every morning. Open 7 days a week, Monday–Friday: 7 a.m. – 8 p.m., Saturday: 8 a.m. – 8 p.m., Sunday: 8 a.m. – 7 p.m.
You can’t go to Boston and not visit an Irish Pub and get some Samuel Adams Brewery drinks. Again, highly recommend making a reservation. It was so packed when we visited but we sat by the window and people watched as we enjoyed our food and beer. I had the Shepherd’s Pie and my mom had the Taste of Ireland. It was all delicious and we make an effort to come back every time we’re in Boston. They’re open every day from 11 a.m. to 2 a.m.
There was one morning when we wanted to explore and hit the ground running so we hit up Flour Bakery for coffee and a pastry. They have several locations in Boston that are open at various times.
So the great cannoli debate of Boston: Mike’s Pastry or Modern Pastry> We only went to Mike’s because my mom had been there before. They only take cash and we got a nice assortment of cannolis and eclairs. We also bought a small cooler at a local pharmacy and put them in there. When we got to the airport we got ice at a spot at the airport and enjoyed them when we came home! Open Sunday to Thursday from 8 a.m. to 10 p.m. and Friday to Saturday from 8 a.m. to 11 p.m.
A great little Greek restaurant that was great for wine and appetizers. I wish we were hungry enough for dinner but it was a great laid-back spot and I loved the ambiance! They’re open Monday- Wednesday from 11:30 a.m. – 12 a.m. and Thursday – Saturday from 11:30 a.m. – 2 a.m. and Sunday from 11 a.m. – 11 p.m.
Shopping on Newbury Street
You know how much I love shopping! It’s a lovely walk and you shop at Reformation, All Birds, Patagonia, Anthropologie, and higher-end designers like Chanel, Tiffany, Burberry, and Cartier. There’s an AMAZING Restoration Hardware that you have to check out too. If you want to just see the cobblestone streets and window shop it’s a lovely street to walk down.
Take a Stroll Around Boston Public Garden
After you’ve walked Newbury Street, you might find yourself at the Boston Public Garden. It is so pretty here in the fall with the gorgeous colors against the pond and the big beautiful trees! We also had fun watching all the dogs try to chase the squirrels. Plan ahead and pack a picnic and a book to enjoy the park in its full splendor and glory.
Walk the Freedom Trail
You can book a trail walking tour, but we decided to walk it on our own at our own pace and look up the history from our phones. The Freedom Trail Walking Tour includes places like Boston Common, Old North Church, Old South Meeting, Boston Massacre Site, Park Street Church, South Meeting House, Massachusetts State House, Paul Revere House, and the Bunker Hill Monument. On a nice day, it’s a lovely walk! You can stop and eat and do whatever you like along the way. If you like tours, this is a fun one.
Explore the Boston Public Library
Not going to lie, I wanted to go here to see where they filmed some of Legally Blonde! It’s a beautiful building that you’re free to roam around and explore. Make sure you’re quiet! Students are all-around studying. They’re closed on all holidays and closed on Mondays. They’re open Tuesday – Thursday from 9 a.m. to 9 p.m., Friday and Saturday from 9 a.m. to 5 p.m., and Sunday from 1 p.m. to 5 p.m. (Also drop in for high tea or a drink at their Map Room Tea Lounge.)
Isabella Stewart Gardner was a Boston socialite who turned her home into an art museum. She loved to travel and collected different pieces from Europe, Asia, and North America. She has paintings, sculptures, tapestries, and other fun decorations. One interesting thing about the museum was it was robbed in 1990 and 13 pieces were stolen and never recovered. Plus the grounds are stunning.
Get Artsy at the Institute of Contemporary Art
We ventured out of Back Bar into the Seaport District for the ICA museum! We saw lots of great exhibits and enjoyed the Sea view here. If you get hungry after looking at the art Committee (mentioned above) is right next to the Institute of Contemporary Art.
Stop and Enjoy the View at Boston Harbor
Walk around, cross the bridge and see the Charles River and party ships. It’s a piece of history to see where the Boston Tea Party happened and the tea party ships.
Absolutely! Two to three days is the perfect amount of time in Boston.
It’s in the Kenmore Square area.
June to October is the best time to visit! I loved October since it was a little brisk but still nice enough to be outside.
And there you have it! Our 2 day itinerary in Boston! We did so much walking, eating and sightseeing. There was still so much on our list! I want to go back again in the fall and hit up Harvard and some other restaurants. I also want to go back to visit the New England Aquarium, Old State House, Faneuil Hall Marketplace, and Omni Parker House. Can’t wait to visit again soon!