Boston Bucket List for Young Families


Our little family spent a week in Boston at the end of August, and it was one of our favorite trips together so far. We went for the pure fun of the city and had the most relaxing, enjoyable time exploring, resting, and site seeing. I thought I’d share a list of links for any of you that may be planning or thinking of planning a trip to Boston. I used my iPhone for most of our pictures in the city so if you’re looking for those, just visit my INSTAGRAM and search for the hashtag #bostonbreak2014.

//Vacation Rental by Owner was a great resource for us in finding a place that was ideally located within the city and easily accessible from the T {Boston’s subway system}. The apartment I linked is where we stayed. It was stocked with everything you could possibly need for a week’s vacation. Trader Joe’s was within walking distance so it made our meal planning very simple. The only drawback is that there isn’t a washer/dryer within the building, but if you pack enough clothes, you’ll be perfectly fine. Compared to staying in a hotel, it’s on the pricier side, but we had a kitchen to prepare our meals in, never had to pay for parking since we used public transportation instead of brining a car, and had a separate room from where our daughter slept in the living room. Also there are apple TV’s. Enough said.

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//The T made it possible for us to get wherever we wanted to go in the city and was very easy to use. We recommend downloading the app, Embark Boston, to easily access route directions and train schedules. Catching the silver line from the airport is free, but you’ll need to buy a Charlie Card to exit the station if you switch trains. A 7-day pass is $19.99.


//The Public Garden was one of our favorite places to take Aletheia and to enjoy picnics. The swan boats from Make Way for the Ducklings was a special memory since we had brought the book to read on the airplane. Being able to connect real life with a story from a book was such a fun way to help her experience life in a new way.


//The Frog Pond is right next door to the public garden and is a huge wading pool for kids to splash around in and enjoy unhindered fun right in the center of the city. There is also a carrousel next the pond, options for lunch, ice cream treats, and an awesome playground. Pack their swimsuit when you plan to visit or bring a change of clothes. I also heard the pond is transformed into a skating rink during the winter months.

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//The Boston Hatch Shell and the Landmark Orchestra put on a majestic performance along the esplanade that was free to the public and such a fun evening. Check their event schedule to see if there is anything scheduled during your trip! It’s a great way to encourage kids to love the arts and enjoy new experiences.

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//Walking/Running the Esplanade was such a fun way to spend lazy afternoons or evenings. There are several great parks along the river and a great running/walking/biking path for exercising with a view.

//Kayak the Charles River for a new perspective on the city. Rentals are around $20.00 for an hour, life jackets included, and kids are welcome aboard the canoes.


//Fenway Baseball Park is a must for your trip if you’re visiting during baseball season. Even though the Boston Red Sox lost miserably, we had a fantastic time.

//Modern Pastry is another destination you don’t want to neglect. Unless you’re on a diet, then you should definitely avoid it. Because it’s amazing, and one dessert might not be enough. The line was out the door and down the street when we arrived. That’s how we knew it was going to be amazing. It’s cash only so be sure to pack a $20 just in case. You’ll be shocked at how much you can get for under $20 there. Out of this world cannonli’s and key lime pies, but at little cost. If Aletheia hadn’t been so tired, I would have gotten back in line for an extra large peanut butter cup. Besides they wrap your purchase in a cardboard box with baker’s twine. Who can resist baker’s twine?!


// The Cape Flyer was such a fun way to get outside the city and visit the coast. We took a whole day to take the 2 hour train ride, relax on the beach, eat fish and chips, and stroll through the little city of Hyannis. There’s a free trolly that picks you up from the train station and takes you all over the area so it was easy to get out to the beach. It was one of the loveliest days I can ever remember. But please, put sunscreen on, and don’t forget your feet because Daniel couldn’t walk for days after that trip he got burned so badly. Also the seagulls are very bold and will make off with your food if you turn your back on it or leave it outside of the cooler. So be vigilant or pack up your chips when you’re not munching on them. We observed many a theft that day. A round trip aboard the cape flyer is $40.00/person. Kids are free.

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//Walk/Run Along Commonwealth Ave sometime during your trip. Our apartment was one street over so we got to almost every day. It’s a gorgeous tree lined path down the middle of the street with benches and beautiful monuments and sculptures.

//Newbury Street Shopping/Dining is another area to make a beeline for during your vacation. Such a fun area with so many possibilities. All my favorite shops were there in the most beautiful old row buildings. This area was also within walking distance from our apartment and very close to where Trader Joe’s is located.

And that was our trip! Really one for the record books.



  1. What a great list! I have wanted to go to Boston for quite awhile now. We’ve used AirBnB for many trips and if a rental is available they are so much better than hotels. Having access to a kitchen is so nice.

  2. Teresa says:

    These pictures are beautiful! It looks like you guys had an awesome time. Thanks for the tips and places to visit! hopefully we can make it to Boston sometime soon :0)

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