In September 2023, we attended my friend’s wedding in Maine, leaving the kids at home. We had one day to explore Boston, so I’ll be sharing what we did.

Boston is a city I have always wanted to visit. Leading up to the trip, I wanted to have a detailed itinerary ready, but I just didn’t get to it. We explored the city with another couple, dear friends of ours from Idaho who also have young children.

We all love our children, but it sure was nice to just have an adult day, walking around, eating, drinking, and being merry, and really just going where the wind blew us.

Hopefully, this post can help serve as a starting point for some plans you might be thinking about to explore Boston. And if you have suggestions of things we should have done, feel free to leave a comment!

Lodging

To our surprise, our friends were able to arrange free lodging for us through friends of theirs. But, we originally had reservations at The Revolution Hotel which we ended up cancelling. I chose The Revolution Hotel because it seemed like it was a nice location (walkable and close to public transportation), reasonably priced, and unique. My friend also suggested we stay at The Charlesmark Hotel, but there was no availability.

Overview

This point contains affiliate links which means I may receive a small commission at no additional cost to you if you make a purchase.

For our day in Boston, we were out for about 14 hours and walked a little over 8 miles. I am by no means a fashion expert, but I thought I’d share what I wore. I wanted to try to look decent I guess (not sure if I achieved that or not), but comfort was definitely my priority. Here’s how I dressed:

  • Footwear – I have arthritis in my feet so comfortable shoes are imperative for me. That day I wore New Balance Cross Trainers and my feet felt great. I had no issues at all and those shoes were very comfortable and cute. I wore sneakers because it was a little chilly, but if it were a warmer day, my backup shoe option was Teva Midform Leather Sandals which have become a new favorite comfortable fashion sandal for me.
  • Socks – I find it tricky to find a low-cut sock with a more fashionable sneaker. But, I’m glad I had my Hide and Seek No Show Smartwool Socks. They worked great.
  • Pants – I’m pretty comfortable in jeans so that’s what I wore. Another choice I would have considered is my beloved prAna Halle pants that I wear for a variety of activities.
  • Shirt – I wore a prAna foundation v-neck top. I love the fit and basic look of these tops which is why I have multiple in different colors and wear them all the time.
  • Purse – With beautiful weather and no kids, I just wore my outfit and took a simple crossbody bag. It felt so great to travel light.

With that said, let’s get into how we explored Boston.

Based on where we stayed, we started walking toward a breakfast spot and immediately noticed that Boston was a beautiful city. With the weather on our side, we really enjoyed just walking around.

We headed straight for breakfast and were very happy with our choice at Pressed Cafe.

This image has an empty alt attribute; its file name is download-1-8.jpeg

During breakfast, we discussed some plans for the day and we decided we wanted to visit the Cheers Bar. With a tentative map in my head, I thought we should go there first as some of my other planned stops were headed in an opposite direction.

So after breakfast, we headed directly for The Cheers Bar passing through the gorgeous Public Garden.

We enjoyed just walking through and taking pictures, but you can consider a swan boat ride here.

I’ll admit, I’m only vaguely familiar with the show Cheers. But, I still enjoyed having a drink at the bar that inspired the show. We noticed a bar in the basement, but we decided to have a drink in the brighter more spacious bar upstairs near the gift shop.

It worked out well that we visited right when it opened. It started to fill up a bit around lunchtime when we decided to head out. From there, we headed toward The Freedom Trail.

The Freedom Trail is a 2.5-mile walking tour through 16 historic sites. If you aren’t sure what to do in Boston, The Freedom Trail is a great place to start. You just follow the brick path taking all the navigational stress out of it. The trail leads you to several historic sites plus it passes a ton of pubs, eateries, cafes, and more.

We began The Freedom Trail at The Boston Common Visitor Center where we used the restroom, and picked up a brochure for $3 for a self-guided tour. You can look into scheduling a private tour, joining a group with a tour guide, and even exploring the trail with the app.

You can get lost exploring so many historic sites in the heart of the city. We read about some history on the brochure I purchased and signage provided with mostly brief stops. However, you can go more in-depth. Some of the stops are set up like museums with entrance fees for more extensive tours.

Personally, I loved seeing the narrow streets, cobblestone alleys, and the old architecture mixed with the new, all while learning so much about American history and The Revolution.

After exploring some sites on the beginning portion of The Freedom Trail, we developed an appetite for lunch so it was ideal that the trail lead us right to Quincy Market.

This was definitely a popular spot on the trail that offered several delicious-looking food options inside. But when in Boston, we had to try lobster and clam chowder. Although it was a little pricey, sharing a few items from Boston Chowda Company was worth it. My personal favorite was the hot lobster roll.

After Quincy Market, we wanted to walk off lunch and so we continued following The Freedom Trail.

We passed by several pubs, cafes, etc that caught our eye through Little Italy (I believe this area is also called the North End) and elsewhere. I haven’t spent much time in Europe, but it felt very European to me.

We followed the trail to The Paul Revere House where we decided to spend a few bucks and take the tour.

The Freedom Trail continued to several more stops, but this is actually where we stopped following the trail. We started backtracking into Little Italy and stopped at the famous Mike’s Pastry. I think another famous stop in this area is The Modern Pastry Shop.

Our friends from Idaho never had a cannoli or Boston cream pie. So we picked up a few sweets and enjoyed them over cappuccinos in a nearby cafe. Those cannolis were amazing.

At that point, we definitely had some full bellies and backtracked to a green space for a few minutes to take in the sites of the city on some neat swings while we digested.

Then we wanted to go explore a few historical pubs that caught our eye along The Freedom Trail. We first stopped at The Green Dragon – “Headquarters of the Revolution.”

Then, we hopped across the street to Bell in Hand Tavern – America’s Oldest Tavern (1735).

Although my belly was full, it was getting late and my friends had an appetite for dinner. We saw so many amazing places in Little Italy so we decided to head to that area for dinner.

One place in particular, Aqua Pazza, was making pasta in the window and it caught our eye. To our luck, they were able to seat us for an unforgettable meal. I would not have imagined anyone would order a burger in an Italian restaurant, but they guys split a Wagyu burger that was so delicious they’ll never forget it.

But it looks like you can’t go wrong in this area. There were so many amazing-looking options.

As we were heading into the evening, we could have easily gone home to bed at that point, but we knew the time with our friends (without kids) was rare, so we pushed through for one more outing. We wanted to walk some more and we were in the mood for some sort of adult gaming activity to keep us awake frankly. So after dinner, we started walking toward the Seaport District.

We initially considered going to Puttshack for an upscale mini-golf experience. Instead, we decided to check out Flight Club Darts. Unfortunately, it was closed for a private event. But, to our luck, Kings Bowling was available in the same building.

We enjoyed a few rounds of bowling, and after a long day, we finally took a taxi home and called it a night.

My friend lives in Maine and here are a few specific recommendations she had for us that we didn’t get to:

And that was our long fun-filled day in Boston! I hope you found this itinerary helpful. If you did, and you end up adventuring in Boston, please tag me on Instagram (@adventureswkelly). I’d love to see your adventures. If you know more about Boston than I do, please feel free to share some suggestions.

Other Travel Itineraries

After our day in Boston, we headed to Portland Maine. Be sure to check out how we explored Portland Maine for a few hours before my friend’s wedding festivities began.

Additionally, check out some other travel itineraries I have:

Happy Travels!