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Boston Disappoints: Why The Best Time to Travel Had Us Running Back Home

by victoriavadenking
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best time to travel to boston

Let me tell you, trying to figure out the best time to travel to Boston was the least of our worries.

We recently took a trip to America’s favorite city, and let’s just say, it was a bit of a nightmare.

Our airline canceled our flight as soon as we arrived to fly out (and then did the same on our departure).

It took us an hour, but thankfully another (and better) airline immediately (and willingly) accommodated us.

After hearing SO many amazing things about Boston, we had high hopes for visiting this historic city.

But, after finally arriving to explore all that Boston had to offer, I must say, I was left feeling rather underwhelmed.

This post is an honest look at the best time to travel to Boston.

best time to travel to boston

Ah, Boston in the spring – the perfect season to visit, except for one little thing: allergies.

After our harrowing experience getting to Boston, I was ready to abandon this city altogether.

But, I must say, visiting in the spring was definitely the best time to do it.

As a family of allergy sufferers, we were a bit nervous, but let me tell you, the air quality in Boston is no joke.

The city’s location on the water helps keep the air quality top-notch.

My kids didn’t need their inhalers once during our trip, and my husband even stopped snoring at night (a miracle, I tell you!).

And the cherry blossoms in the Boston Public Garden were in full bloom, providing the perfect backdrop for a family photo op (yes, I’m that mom).

Plus, the city wasn’t overrun with tourists, with school still in session for most colleges and universities.

So, go ahead and pack a few extra Kleenex, but you’ll be surprised that you can actually enjoy the beauty of Boston in the spring without sneezing.

best time to travel to boston
Outside the Boston Tea Party and the Boston Children’s Museums

Maybe we should start with the positives…

Why We Chose Boston

Let me start by saying that our trip to Boston was…underwhelming, to say the least.

We traveled as a family of five with small children and flew into the Boston Logan International Airport.

Our trip was for my husband’s graduate course, and we stayed at the Boston Marriott Cambridge (more on that later), which was a good middle ground between exploring downtown Boston and his travel to grad school.

Plus, we got a discount with my husband’s credit card, which was a no-brainer! (Or so we thought.)

Boston is the Definition of Cleanly

Boston, the city of clean streets and friendly folks.

It’s almost like they invented the word “tidy.”

Not a gum wrapper in sight or a stain on the sidewalk.

You could practically eat off the pavement, but I wouldn’t recommend it.

Plus, the locals are just as nice as their streets are clean.

No snobby attitudes or pretentiousness here, just good old-fashioned helpfulness.

Thank goodness for the T, Boston’s train system, because there were two stops just outside of the hotel which was extremely convenient.

I may have started out as a rookie, but I quickly became a pro at navigating the local tram like a real Bostonian.

best time to travel to boston
The Esplanade at the Charles River had breathtaking views

Safety Was My Biggest Concern

As a mom on the go with three young kids in tow, feeling safe is my top priority.

And I kid you not, Boston did not disappoint in that department.

It’s like the city had a personal bodyguard assigned to every corner.

Even with everything going on in the world, my husband and I felt more secure in Boston than anywhere else we’ve been.

We even let our kids play in the park without hovering over them like helicopters.

And despite our rollercoaster of mixed emotions, the safety and security in the city made us consider moving to Boston permanently.

best time to travel to boston
Boston North End Park

When is the cheapest month to visit Boston?

If you’re looking for a cheap trip to Boston, you might want to rethink your strategy.

This city is one of the most expensive places to visit in the United States.

But hey, who needs money when you have charm and character, am I right?

If you’re dead set on visiting Boston on a budget, you might want to consider coming during winter when the tourists are few and the snow is plentiful.

And while you might be shivering in your boots, at least you’ll be satisfied knowing you got a good deal on your hotel.

But, if you want to experience Boston in all its glory, I suggest you save up and visit during the spring (or warmer months) when you can actually enjoy the weather and the city all in one.

How many days in Boston is enough?

Well, that depends on your definition of “enough.”

You’ll need at least a month if you’re like us and want to see and do everything like a local.

But if you’re like normal people with limited vacation time, I’d say 5-7 days is a good amount of time to experience what Boston has to offer.

We stayed for eight days, a good amount of time for my husband’s grad course and some family fun.

We could see most major tourist attractions and even relax at the playground while the kids ran around like wild banshees.

best time to travel to boston
Boston Public Transportation was way easier to navigate than New York

Bostonians Lost In Translation About Their Own Transportation

The “T” is the local tram (or subway) system in Boston and is a mom’s best friend.

If you want to get around Boston like a pro, forget about the taxis and Ubers, and hop on the T instead.

With my husband away in classes, I was a solo mom of three very excited kids.

Without a car, it was super convenient to feel safe and secure with the new logic of maneuvering the city for reasonable public transportation.

In Cambridge, we frequented the Alewife/MIT (red) lines in and out of downtown, but all routes were just as clean and efficient.

But hold up; there’s more to the T than just the regular lines.

There’s also the Silver Line that runs from the airport into downtown Boston.

Sounds great, right?

Well, it would be if anyone at the airport knew how to catch it!

best time to travel to boston
The infamous (and mysterious) MBTA Silver Line

Our first impression of Boston Public Transportation

Everyone raves about how it’s easy-peasy to get around Boston with public transportation.

Still, we were stuck at the airport with no clue how to get to our hotel in Cambridge because our “only option was by taxi or rental vehicle.”

We waited 20 minutes for a taxi, only to be crammed in the back with our baby boy on my lap for a 40-minute ride that cost us a whopping $70!

Thankfully, my husband’s classmate, who we met for the first time that week, clued us in on the Silver line (which we took on our departure flight).

And let me tell you, and it was a godsend!

The Boston “T” tram system was very clean and always on-time

If you buy a day pass for just $11, you can ride multiple times throughout the city (and you won’t be crammed in the back of a taxi going over bridges during rush hour).

Plus, the Charlie Card made it easy to hop on and off the tram without fuss.

Oh, and did I mention that kids under 11 ride for free?

Don’t make the same mistake we did, and take advantage of the T’s Silver line for a safe and affordable ride into downtown Boston!

best time to travel to boston
Cambridge was pleasant but not what we were expecting.

Cambridge Is Nice, But Meh

Now, don’t get me wrong, Cambridge was lovely.

It’s a great city for young professionals and Harvard students, but I was not entirely impressed.

As a mom of three, it was slightly annoying having to haul the kids into the city all the time.

While having a peaceful night’s sleep was nice, everything around us closed early.

We found out the hard way when I realized I had forgotten my contact lens solution, and the milk for our baby boy spilled.

The closest drugstore was a few miles away, and I had to double for delivery since our Uber driver had to come from a few cities over.

Lesson learned, staying downtown with its convenience and 24-hour stores is key when traveling with kids.

best time to travel to boston
Boston Marriott Cambridge had construction going on during our visit

A Mediocre Hotel in the Wrong City

Okay, let’s talk about the Boston Marriott Cambridge again.

If you’re in Cambridge for business, this is definitely the spot to be.

It has easy and direct access to the T, which is always a plus.

But, let me be honest with you, it’s, at best, a 3-star hotel.

I found several bits of hair in the bathroom, our hand towels, and the tissue box, but the staff quickly cleaned it up and apologized.

best time to travel to boston
We had a nice view at the Boston Marriott Cambridge

However, the gentlemen who work the Bell Stand made our experience because you could tell how much they loved their city.

Their wealth of knowledge was much appreciated, especially since it was our first trip to Boston.

Regardless, if you’re visiting Boston for the first time (and let’s be real, the best time to travel to Boston is always the first time), I would suggest staying in the actual downtown city.

To be fair, I didn’t want my husband to commute far for his class just for our convenience, and with our added discount, it only made sense to book at the Marriott.

Sure, it’s a great spot for business travel and has easy access to the T, but we didn’t get to experience the city of Boston—well…because we were in Cambridge.

Boston Children’s Museum was amazing but short-lived.

Boston Children’s Museum was Short, Sweet (and Sour)

The Boston Children’s Museum is a must-visit if you’re traveling with kids.

It’s an interactive, hands-on experience that even adults will enjoy.

There’s something for everyone, from the climbing maze to the bubble room.

Unfortunately, our experience was a little tainted and extremely short-lived due to the pandemic (2022).

We didn’t know that the museum was closing for cleaning at midday and found out when we arrived.

So, we only had 30 minutes to explore, and my kids were very cranky when we had to leave suddenly.

But we would visit here again, especially during the spring, because I felt guilty about seeing their faces having such “rushed fun.”

best time to travel to boston
We were able to meet up with college friends at the Esplanade

The Ultimate Playground for Kids and Parents Alike in Boston

Springtime is the best time of year to visit Boston because you get to really enjoy the outdoors here.

The Charles River Esplanade is a green space that is the perfect place to do just about anything.

We picnicked, lounged, napped, studied, brought the kids…you name it, we did it.

And let me tell you, and it’s a huge area.

So, if you’re meeting people there and you’re not from the area, you’ll definitely need to pin-drop your location.

But, aside from that, we had an amazing time.

Honestly, the prettiest view of Boston

The people were friendly, there was an ice cream truck nearby, and we even stumbled upon a free concert.

We watched a salsa class dance on the dock while we soaked up the sun.

And the best part? It was CLEAN!

You don’t find that in many parks these days.

The kids had a blast, and we ended up staying for hours.

It’s impressive how safe the city feels, especially in a huge park like this.

best time to travel to boston
Food at the Commonwealth was…okay.

Tales of Tasting Mediocre Food in Boston’s Best

If you’re a foodie looking forward to Boston cuisine, hold on to your taste buds because I’ve got some tales to tell.

Boston is renowned for its delectable seafood, innovative dishes, and fantastic dining options.

However, we experienced a few mediocre meals that fell short (really short), despite being highly recommended by locals and visitors alike.

best time to travel to boston
Boston seafood is pricey, but worth it!

Overhyped and Underwhelming

As for the food scene, we were excited to try Legal Sea Foods, which locals, blogs, and YouTube videos highly recommended.

Unfortunately, we were slightly disappointed with our experience.

While the location was amazing, and we were seated near the water without having to wait, our food was nothing to brag about—except for the oysters, which were impeccable.

However, the cheeseburger I ordered from the kid’s menu was not properly cooked and was still raw.

And the mac and cheese our friends ordered (also for a child) tasted like aspirin.

best time to travel to boston
My kids were given undercooked burgers!

Seafood to Die For…But at a Cost

Let me tell you, the seafood in Boston is honestly exquisite.

And I’m saying this as someone who lived in Florida for four years.

But it comes at a cost.

The Union Oyster House blew me away!

We paid $3 per raw oyster.

That’s right, three whole dollars (so, of course, I ordered several)!

But, hey, when in Boston, right?

best time to travel to boston

It was our first dining experience in Boston and the reason we would return.

The customer service was top-notch, especially since we had our small children.

They seated us away from the crowds next to a window, which we greatly appreciated.

The servers were incredibly knowledgeable about the menu and very friendly.

And, oh my gosh, the oysters were out of this world!

They were definitely on the pricey side, but every single bite was worth it.

best time to travel to boston
Commonwealth Restaurant in Cambridge

The Food Will Make You Think Twice

In walking distance from our hotel in Cambridge, Commonwealth was a lovely restaurant, but if you’re looking for an exciting culinary experience, keep walking.

Having been vegan, vegetarian, and pescatarian, the menu was minimal.

The food reminded me of the stereotype you hear when “healthy food has little taste.”

Commonwealth seems like an excellent restaurant for someone on a diet to splurge once a week.

Our server was knowledgeable and accommodating.

The Shishitos were the highlight of our meal, so much so that I ran out to buy them when we got home.

It seems to be a popular spot for the young professional crowd, as the outdoor seating was already booked before dinner and quickly filled up as soon as we arrived.

best time to travel to boston
Shishitos are the best thing on the menu at Commonwealth!

A Sweet Escape from Disappointing Dining Experiences

Another food spot that we were eager to try was Mike’s Pastry.

The lines were long, and the place was crowded, but the food here actually lived up to every single one of our expectations.

It’s family-owned, and they’re used to dealing with the indecisiveness of tourists like us.

The staff was patient and polite the whole time, even when my kids couldn’t decide what to order.

Mike’s Pastry, you won us over in the end.

best time to travel to boston
The infamous Mike’s Pastry in Boston

This post was all about the best time to travel to Boston.

Well, there you have it!

Boston may not have been everything we expected, but it certainly gave us plenty of stories to tell.

From our adventures with Boston’s T to our hit-or-miss experiences with local eateries, it was a trip full of ups and downs.

Spring was truly magical, and despite the allergies, it was undoubtedly the best time to travel to Boston.

The weather was just right, and you could explore at your own pace without feeling rushed or overwhelmed.

While our trip was a bit of a rollercoaster ride, with some misadventures here and there, we still managed to have a good time.

So, before you pack your bags and head out, research and set your expectations accordingly.

Oh, and don’t forget to follow us on Instagram for some unfiltered, real-time Do You Even Mom moments because, let’s be real, traveling with kids is always an adventure.

best time to travel to boston

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victoria vaden

a diaper duties mom blog


victoria vaden king

Victoria Vaden

Original YouTuber when ‘viral’ was just a flu symptom. My English degree qualified me to tell stories (the good kind). So, I'm sharing the not-so-normal reality of motherhood and marriage.

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DYEM is for the not-so-perfect, spit-up-stained, smile-through-anything moms out there looking for sanity. Motherhood is messy and full of mistakes. You'll find plenty of that here.

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