In this post I’ll be sharing our recent getaway to Boston with our toddler. Throughout, you will find our itinerary and recommendations. You can scroll to the very end to find quick notes of our takeaways from the trip pertaining to traveling with a toddler.
Around the same time four years ago, Tony and I visited Boston, Massachusetts and thoroughly enjoyed ourselves. Boston has a lot to offer from its detailed architecture, festive foliage, many parks, and fresh seafood. We knew we’d one day want to visit Boston again, but, at the time we had no clue our next visit would be with our very own SON! It’s one of our dreams to share traveling experiences with Isaiah (and of course any of our future children)! We have learned and created the most memorable moments traveling together and to do so with our kids is a huge blessing.
Today’s circumstances with COVID had us timid about traveling, especially with our 19 month old. We knew we’d be taking a risk if we traveled so we carefully thought everything out. A couple of things we considered: Boston’s COVID rates are low and under control— huge plus. Our interaction with other people would be lower than our interaction with people in Houston — another huge plus. Boston has a ton of outdoor things to do and October is a great time to experience its foliage. Plus, plus, plus! So we took a chance, booked our trip, and ended up in Boston for 5 days!
:: Day One ::
We left on a Thursday morning at 8:45 am, had a less than 2 hours layover in Charlotte (a break for Isaiah to burn some energy), and landed in Boston around 3:30 pm. There was no traffic from the airport to our hotel. Per our Uber driver, “traffic has been nonexistent since COVID”, which made all the difference in making the most of our day. Once we arrived to our hotel downtown, Loews Boston Hotel, we checked-in and got situated in our room. Soon enough, we were ready for dinner!
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Tony discovered a black-owned restaurant for our awaited Thursday night dinner at Darryl’s Corner Bar & Kitchen. We were seated on a well lit outdoor patio, which for Boston, is normal as they have suitable weather to do so in October. It was roughly 70 degrees and became cooler as the night went on. Tony and I began with alcoholic beverages while Isaiah indulged in the mini cornbread and plantains (we’re in a stage between a picky-eater and textures). Both were a great choice and shareable. Tony had the “Bobs Glorified Catfish” and I had the “Chef Fish Club”— we recommend trying both or even visiting Darryl’s Corner Bar & Kitchen on a night when they have live jazz music!
Around 8:30 pm we were lounging in our hotel room, laughing, and playing with Isaiah until he fell asleep. This was one trip we didn’t have to be asleep early to wake up early. So, the entire trip all three of us fell asleep and woke up when our bodies told us to.
:: Day Two ::
After a reviving night of rest and sleeping in until 9am (huge win for us), we were ready for our second day in Boston! The weather forecast predicted 80-90% percent chance of rain starting at 3pm so we had very little planned this day but we truly made the most of it.
By 11:30 am we were brunching at North Street Grille . We waited less than 5 minutes due to making a reservation which I highly recommend due to COVID. Otherwise lines and wait times are long. We were seated outside where the weather was cool and sunny— perfect for us! While waiting on our food, I took a walk with Isaiah to a nearby park so that he could burn some energy.
Isaiah and I shared pancakes, turkey sausages, eggs, and potatoes (not pictured). Tony indulged in the chicken and waffles plate. We feasted and left North Street Grille very pleased!
After brunch, we found ourselves strolling Boston in route to our next destination. The foliage was vibrant even as the skies prepped for the oncoming rain. It was just what we needed. So much so, that one of us dozed off! Can you guess who!?
We arrived at the New England Aquarium just as the rain began. Our tickets were purchased online prior to arrival which might’ve assisted in our quick check-in. Yes, Isaiah was still asleep, but not for long! Tony got us situated with start and endpoints while Isaiah and I made a quick restroom stop. I found the restroom to be very clean and appreciated the reserved changing station. A huge plus when traveling with a toddler. North Street Grille does not have a changing table of any sort.
It was Isaiah’s first time being at an aquarium and he seemed to be thrilled with just about everything. Except for one thing…. the tank of schooling fish- ha! I wish we were able to capture his reaction but we were too busy in the moment. The penguins and the sea turtle was by far our favorite so we spent majority of our time observing them.
After 2-3 hours, we were headed to the Boston Market for lobster rolls and clam chowder! They have some of the most buttery and flavorful lobster rolls in Boston for a tad cheaper than the local restaurants. Other things to explore are desserts, shopping, lounging, entertainers such as musicians, and of course more food.
The rain stopped with just enough time for us to snap a few family pictures and allow Isaiah to run through the light sprinkles. We were back at our hotel by 4pm and spent the rest of day there enjoying the rain fall, movies, napping, lounging, and ya already know– TAKEOUT!
By 7:30 pm, we were all bathed and ready for dinner when Tony walked in with not just Asian food for dinner, but MARGARITAS too! He is quite the spontaneous man so it was by no surprise he ventured off and found a golden spot with margs. We feasted and all dozed off at different times until the next day!
:: Day Three ::
Our third day in Boston was our FAVORITE! The weather was PERFECT– sunny and cold enough for a light coat/jacket. We were feeling like locals and went with the flow.
Our day began with a 15 minute walk to brunch at The Beehive. The outside patio was immediately available upon arrival and we were happy we scored our seats on such a beautiful Saturday! Tony and I ordered mimosas and the coffee cake du jour with honey to share with Isaiah. It was quite delightful and Isaiah couldn’t resist saying “mmmm” after each bite! Our food was out quick but hot and fresh just like we love it. We each ordered the french toast, bacon, and eggs and we ate it all! This was our favorite brunch of the trip.
The rest of our day was spent at Boston Common Park. Its a huge park highlighting Boston’s colorful foliage and an abundance of space for kids to run and play. So we ran through the park and played with Isaiah for a couple of hours. He had so much fun sprinting across the grass and dancing to the music that he reached a point of exhaustion and was ready for a nap. While Isaiah napped, we toured The Black Heritage Trail .
Beacon Heritage Trail is a 1.6-mile walking tour that explores the history of Boston’s 19th century African American community who primarily lived in a small section of a neighborhood in Boston called Beacon Hill. Boston is known for The Freedom Trail which highlights the American Revolution using historical sites such as homes, churches, ships, burying grounds, and more. Tony and I walked the tour when we visited years ago. I would recommend it for the experience and to compare the two for yourself. We toured majority of The Black Heritage Trail but had to cut it short because Isaiah would soon awaken and we needed to grab food. So we ended at the museum portion of the trail which we found out was closed during our visit. We were a tad bummed.
Our stroll landed us in Boston’s ‘Little Italy’ which was a region of Italian restaurants and shops. It did remind me quite a bit of our trip to Italy. We circled it, enjoyed a few light refreshments, and ended up back at Boston Common Park for another 2 hours.
We ended our evening being indecisive of dinner plans until Tony had a brilliant idea to order food from the margarita spot next door that he discovered the previous night. We scored big time because not only were the margaritas a hit again but the food was definitely worth the time wasted pondering!
The name of the restaurant is Citrus & Salt. We ordered the baja fish tacos, blue crab empanadas, and the smoked chicken and potato taquitos. Everything was great, but my favorite were the empanadas! Their servings are somewhat like tapas so I would recommend a couple of orders of each dish if you plan to share.
:: Day Four ::
If you haven’t noticed, sleeping in and brunch was the morning thing of this trip. I mean, what more can two parents and a toddler ask for?
Our brunch of choice was Cafe Luna. We forgot to make reservations for this spot so we had to wait about 30-40 mins. Luckily, there was a near by park so we took Isaiah there to play while we waited. Our meals were once again, DELICIOUS! Isaiah and I shared the country biscuit breakfast slider with chicken sausage and a side of potatoes and Tony had the pumpkin french toast, bacon, and eggs. Well worth the wait! I would love to go back for lunch or dinner next time.
After brunch we took an uber to Boston’s Public Library where we briefly witnessed protesting of today’s matters including “Black Lives Matter” movement.
We then strolled our way to Boston’s enchanted Newbury Street. This area of Boston highlights Boston’s most iconic sites from the cobbled streets, top-rated restaurants, and garden paths of the historic Back Bay and Beacon Hill neighborhoods. We spent spent a couple of hours enjoying the live music, vibrant scenery, and cool weather. Isaiah ended up falling asleep and by time he woke up we were at our next destination!
Blackbird Donuts, a charming and chic donut shop, served us well on dessert before dinner! Isaiah may have enjoyed it far more than we did. Since we visited late afternoon, most of the choices we would have loved to try were already sold out. Either way, we appreciated being able to sit peacefully stuffing eating donuts in Boston!
Our night ended with dinner at Atlantic Fish Company. The food here is the BEST! We had so much fun with our waitress who helped us choose the best appetizers, meals, and drinks. We all shared the lobster ravioli which was absolutely delicious! I regretted not ordering this as my main course. Isaiah loved it and we were so impressed! There were a few items on the Captain’s Seafood Platter I was craving so I ordered it for my main course. Tony had salmon, broccoli, and lobster risotto. Isaiah had popcorn shrimp and lobster risotto. Everything including service was VERY EXCELLENT! It was a great ending to our night!
:: Day Five ::
Our last day we slept in one last time! While Isaiah and I got ready, Tony took a quick walk to pick up breakfast from The Friendly Toast. We all shared orders of pancakes, eggs, bacon, sausage, and potatoes. In a matter of time, we at the airport and ready to departure home to Houston!
Overall, Tony, Isaiah, and myself had an amazing time in Boston! We felt safe, happy, and comfortable. Since our return home, we have relived our trip countless of times and still grateful for the opportunity we had to make cherish-able memories with our little family!
:: Takeaways and Recommendations ::
- Decide whether or not to pack all snack, wipes, and diapers/pull-ups, on carry-on, check-in bag, or only enough to last plane ride and then purchase the rest when you reach your destination. Since we checked-in a suitcase, we packed everything and what we needed for our plane ride.
- You can never pack too many snacks! I thought i overpacked on snacks but then we ended up needing to by some at the airport on our way home.
- Plan when and where you will do diaper changes. Not all restaurants have changing tables. We took advantage of brunch spots mostly and it panned out well for us.
- Make reservations at least 24-48 hours in advance. Since COVID, spaces are limited and wait times are extremely long.
- Bring layers of clothing. The last thing you want to do is underestimate the cool weather in Boston. We were very fortunate to have the type of weather we had but I cannot imagine having not packed layers incase of a change in weather. Plus, we found layers better then having to carry around bulky coats and jackets.
- Stay somewhere central. Boston typically has nice weather and to be able to take your toddler on multiple brisk strolls to get to your destinations makes everything more enjoyable and smoother. Especially, nap time!
- Invest in a compact-able stroller. We love our Doona Carseat & Stroller which is a carseat that converts into a stroller! Its been one of our best investments for traveling with Isaiah! The only con we have noted is that there isn’t a storage basket, but that hasn’t been a big issue for us as we pack a fairly light diaper bag. Linked it here.
- Diaper bag essentials: wipes, 4-5 diapers, changing pads, one pair of clothes and socks, snacks, water bottle with water, mittens, light jacket, hand sanitizer, and anything I would put in my purse and Tony’s wallet. O and a phone charger and portable charger! Simple! Our “diaper bag” is a backpack I purchased for traveling. I love it because its spacious. I have it in green and blue. Linking it here.
- Have alternatives. As we all know toddlers may have different plans for our day and quite possibly the weather.
- Bring a tripod for your camera! Strangers often times take blurry pics. SMH.
- Have fun!
I hope you enjoyed this post andor found it helpful if you are thinking of traveling to Boston alone, with a significant other, or with a toddler!
Okay I’m ready for my next trip to Boston…. hahaha I mean FIRST 😅.
Atlantic Fish Company looks AMAZING!!!!!
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Lol! You will LOVE it!
Love this one! I am glad I can always come back to this before we plan a trip with Baby Jonah!
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For sure! Thank you, Anisha!