Big cities can seem daunting to tackle with preschoolers—big buildings, public transportation and attractions that seriously threaten the health of your vacation budget. Boston is one of those cities that may seem impossible to enjoy with a young child without spending tons of cash on entry fees and pricey souvenirs, but it’s actually a place where the outdoor space is nicely complimented by cheap (or free) activities that your young one will love.

Come on, ride the train!
Public transportation is often times our least favorite aspect of traveling, but for a preschooler, riding the rails is a lifelong dream they’ve held on to ever since watching their first episode of Thomas. Grant them that one simple wish and head to the underground. Have your preschooler help you identify which line to take by identifying the right color (there is only red, blue, orange, and green so it shouldn’t take too long) and work together to read the signs or identify trains by their letter. Remind your child that there are a great deal of people and they need to stay close to you at all times. Once the train you need to take has arrived in the station, the real fun begins. If they don’t want to sit comfortably and watch the lights in the tunnels blur past, that’s ok—let them stand. A little surfing lesson on the T is a great way to work on a young child’s balance.

Go green
There is a good chance that you could spend your entire day on and off the green line, which will make navigation in general much, much easier. Make your first destination Government Center. Once you exit the station, hang  a right and head towards the water. The aquarium is a ten minute walk, and once you get there, your child will be delighted by the seals in the tank outside. If marine mammals are the focus of your day, head inside—neither one of you will be disappointed. You can also grab tickets to a whale watch outside of the aquarium or walk along the promenade and watch boats glide back and forth on the bay.

Good eats
Once you’ve waved goodbye to the friendly creatures in front of the aquarium, head back towards the Government Center T stop. You can take a short break at Faneuil Hall for some shopping (there are some pretty neat toy stores nearby) or grab a bite to eat while you sit under the big dome and cautiously nibble as pigeons fly in and out of Quincy Market. This is a great place to find t-shirts, baseball caps, stuffed lobsters and green monsters—basically any child friendly Boston-themed souvenir—for $20 or less.

Don’t skip the Pru
With full tummies, brave another wobbly T ride taking the green train (E line specifically) outbound to Prudential Station. Affectionately known as “the Pru” by the local population, this building stands tall in the center of Boston offering unparalleled views of the city below. Skip the entrance fee to walk around the viewing deck at the top and head to the Top of the Hub restaurant, which sits just below it. Preschoolers will definitely enjoy the view of Beantown, but most likely won’t appreciate it as much as kids who are a bit older, so sitting down to a plate of cookies and a signature cocktail—just for mom and dad, obviously—is the best way to enjoy this attraction together.

Can’t leave without seeing Fenway
Just in case the view accompanied by all the sugar wasn’t enough, the elevator ride down should make your preschooler’s day. From here you can hop back on the Green line or exert some energy by taking a 20 minute walk down Boylston to Fenway Park. Little sluggers will delight in seeing where the Red Sox play, so grab a ball from one of the gift shops on Yawkee Way and walk across the street to the Fens—a public park that will give you all the space you need to perfect your child’s knuckle ball.

For more information visit:
Boston Transit Map
New England Aquarium
Faneuil Hall
Top of the Hub
Fenway Park

Shauna Armitage is a parenting blogger, a freelance travel writer and the co-founder of Pure Wander Magazine. Follow her on Twitter @CarpeCalamus