Hillary Newman Photography

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Downtown Boston with a Toddler

Let’s discuss something. Planning a city vacation with a little one can be incredibly intimidating. It’s a challenge just figuring out where to begin as, undoubtedly, you have many questions. Where should you stay to be near the child-friendly action? What areas are safe? Do hotels offer cribs, rollaway beds and childproofing? How will you ever chase your wild toddler around busy streets and heavily trafficked parks? Will your toddler be overstimulated? These are just some of the considerations that crossed my mind while planning our recent trip to Downtown Boston with a toddler.

Gone are the days where my husband and I can casually pick a city, find the most stylish, highly-rated, boutique hotel, and show up with minimal questions asked. Travel planning has taken a considerable turn for us. But, truthfully… that’s ok! With a little more planning comes the immeasurable gift of seeing a new place through our child’s eyes, brimming with excitement and wonder.

I’m pleased to say we recently succeeded in pulling off a trip to Boston with our two year old and I’m happy to share my tips with you - the good, the bad, and the potentially tantrum-inducing.

Quick tips for visiting Downtown Boston with a toddler

Pick a hotel in the Downtown area for minimal walking

Make use of the trains into and out of the city

Visit the New England Aquarium

Spend lots of outdoor time exploring the Rose Fitzgerald Kennedy Greenway

Check out the Boston Children’s Museum

Grab a treat at Quincy Market

Stroll through the Boston Common

When to visit Boston

The best time to visit Boston is highly dependent upon your interests. While I value good weather and prefer the summer months of May through September in New England, others may prefer to visit during the winter months for particular reasons; including taking in a game at TD garden, etc. This post will focus on the best time for your toddler to enjoy the city fully.

Boston hotels are notoriously pricey, and tend to take advantage of the influx of sports fans that arrive in the city on game nights. For optimal savings on your Boston holiday, avoid days when local sports teams are in town. If you randomly find a night is double the price when trying to book a summer holiday, it’s likely you’ll find there’s a game at Fenway Park.

Getting to Downtown Boston

There are a number of ways to get to Downtown Boston, including the T (Boston’s subway which handily connects much of Boston to Logan airport), trains (entering North Station from the North and South Station from the South), and by car.

As Boston becomes more and more pedestrian friendly, it also becomes increasing difficult to travel by car through the city. The streets can be confusing to navigate and many are narrow and one-way. For this reason, we much prefer arriving by train and leaving our car elsewhere.

Train travel is simple, and incredibly laid-back. You can show up ten minutes prior to your departure if you like. We prepare for train travel by packing minimally. The fewer bags you have to carry on the train, and stow away in luggage racks, the better. For little ones, strollers are able to be transported. You will be asked to fold your stroller, and either carry it with you or place it with the oversized luggage.

Should you choose to drive into the city by car, be sure to consider parking when budgeting. Be aware that parking prices at hotels can be expensive. I recommend looking into this prior to your trip.

Where to stay in Boston

I highly recommend situating yourself right in the Downtown area for minimal walking to and from toddler-friendly attractions. While the Back Bay and Beacon Hill areas are cherished favourites for visiting tourists (and for good reason - they’re beautiful and generally a tad less expensive), they are not situated near the action (apart from the Boston Common). I will note that I may be biased here as I’m approaching my 7th month of pregnancy. Walking long distances has become a huge factor in our planning, but I’d splurge to stay Downtown for any of our future Boston trips.

We recently discovered the incredible, hidden gem, The Dagny. We were pleased with the location and price in comparison to other hotels in the vicinity. The building itself is clearly quite dated, but the interior has been updated to showcase an incredibly cool, industrial steampunk vibe.

Space is a massive issue with these Downtown hotels, so be sure to check if the room size can accommodate all that you require. For instance, a crib can be too large to set up in some of these tiny spaces. When it comes to acquiring a crib, do phone ahead to ensure your hotel offers one if you won’t be bringing your own. We found that despite the high number of visiting families in town at any given time, many hotels did not offer proper, safe sleep spaces.

Things to do in Downtown Boston

New England Aquarium

Located on the Boston waterfront, New England Aquarium is home to thousands of aquatic creatures, including California sea lions, African and Southern rockhopper penguins, and giant sea turtles. The design of the facility is impressive, featuring an enormous cylindrical tank centred in the middle of the main building, with ramps encircling it, creating a four-story viewing area.

There are scheduled training sessions for the sea lions, where you can watch them perform tricks. There is also a touch tank filled with stingrays (with trimmed barbs) for an interactive experience. The aquarium also hosts whale watching tours and a theatre playing 3D films on marine life.

It is possible for admission to the aquarium to sell out during the busy summer months, therefore I recommend booking a timed admission ticket in advance. One option for booking admission at a discounted rate is the Boston Citypass, which includes admission to several other attractions in the city.

Boston Children’s Museum

If you’re looking for a place where your toddler can play and learn at the same time, and expend a lot of energy, look no further than the Boston Children’s Museum. Here, children can get hands-on experience with science, art and cultural-based activities. Some of the exhibits include; blowing bubbles, racing golfballs, making shadows, and a giant water table.

One particularly toddler-friendly experience is PlaySpace, a reservation-only room for 0-3 year olds to explore their interests. There are crawling tunnels, a play kitchen, a train set, a toddler gym and a forest-themed crawling and climbing area. There is a space dedicated to crawlers and also to water play. Our little one had so much fun in this room. I highly recommend making an advance reservation when booking your tickets online prior to your visit.

Quincy Market

Quincy Market is an eatery built in a columnar, Greek style that dates back to 1826. It features grab and go meals from 50+ food stalls and carts, as well as some crafts (mostly located on the exterior of the building). It is an excellent place to go for a snack, whether it be Ben and Jerry’s ice cream, fresh-squeezed lemonade, or a lobster roll (Oof! Watch those prices!).

The main building is surrounded with well-known retail stores where you can do a bit of extra shopping if you please. In summer, you will likely find street performers practicing stunts and showing off various talents in the area as well.

Rose Fitzgerald Kennedy Greenway

The Greenway is a welcome addition to the Downtown Boston area. Built in 2008, this park runs the length of the downtown area, parallel to the waterfront. It includes several adorable additions that allow children and adults alike to get outside and play.

A clear-favourite feature of the Greenway is the Rings Fountain, which features water squirting in unpredictable patterns from 64 vertical nozzles and misters. Another popular attraction is the Greenway Carousel, a ride consisting of unusual animal seats all carved by hand. Your child can ride a sea turtle, a butterfly, a falcon or a sea serpent, and many more. Tickets to ride are $3 each and can be purchased online or in person.

Boston Common

The Boston Common is set back from the waterfront and requires a slightly longer walk to reach. Here, you and your toddler can ride swan boats, have a picnic, and spend time relaxing in the outdoors, away from the hustle and bustle of the city.

Where to eat in Downtown Boston

I will preface this section by saying that many Boston restaurants are currently running limited hours. We noticed that picking a restaurant based on reviews alone and not checking opening and closing times left us standing on the front step, locked out, on several occasions. In general, many coffee shops close early (by 3pm), and many sit-down establishments open late (at 4pm). We also noticed several restaurants opening only Thursday to Sunday. I’m unsure what is contributing to reduced hours at this time, but here are a few places we found particularly reliable.

Lily’s Bar Pizza Patio

Granary Tavern

Tradesman Coffee Shop and Lounge

I sincerely hope this guide helps you plan a flawless, tantrum-free vacation in Downtown Boston with your toddler. Any questions, feel free to leave in the comments section below.

Latah!

Hill XOXO


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