See the Best of Boston in 1 Day

Since my roommate grew up around Boston, it was inevitable that we’d be making a trip to the city at some point so that she could show me around. However, she works Sundays so we had to try all the food and see all the sights of Boston in 1 day. With such a historic city it’s tough to squeeze everything in, but if you only have 1 day in Boston, here’s a great way to spend it.

Brunch at The Friendly Toast

We started our day off with brunch at a little place called The Friendly Toast. This place was absolutely packed and I recommend downloading the NoWait app as suggested on their website in order to reserve your place in line and cut down on the wait time. This is especially important since there really was nowhere to wait inside, so you’ll be stuck standing out on the sidewalk if the weather is poor. The only catch is if you are coming from farther away, the app only let’s you get in line when you are within 20 miles of the location.

Once we got there we only had to wait about 10 minutes until we were seated and the service was quick without feeling rushed. We started with a mimosa flight which had four different flavors to share. Their fare is pretty standard brunch food, but their specialty is Eggs Benedict with multiple different option of the dish available. It was the perfect way to start our day upon arriving in the city.

Boston Public Library

It’s no secret that I’m a bookworm at heart and absolutely adore getting lost in libraries, so when my roommate suggested that we visit the Boston Public Library I of course said yes. Boston has the second largest library in the United States by volume, next to the Library of Congress in Washington, D.C. of course. The courtyard of the old building is the ideal spot to grab a coffee and a good book to peruse on the terrace. We spent some time just wandering the rooms and checking out the beautiful architecture of the building before continuing on our way to walk off all the food we ate.

Boston Common & Public Gardens

From the library, we started our stroll down Newbury Street to the Boston Public Garden. This little park features a pond with some beautiful swans, and several statues depicting famous people and scenes from the American Revolution.

One famous statue in Boston Public Garden is “Make Way For Ducklings” based on a children’s book of the same name by Robert McCloskey. The story was written in 1945 about two ducks that live in Boston Public Garden. The book has now become the state children’s book of the Commonwealth of Massachusetts.

Boston Common sits just across the street to the Boston Public Garden. The site is a historic landmark of the city and dates back to 1634, making it the oldest park in what is now the United States. Today, events and concerts are offered in the summer, and Frog Pond turns into an ice skating rink in the winter months. You can also find the Boston Visitor’s Center on the Common grounds as well. Across the street from the Common you’ll also find the Massachusetts State House, home of the state’s legislative branch.

Freedom Trail

Boston Commons is also the start of the Freedom Trail. The Freedom Trail is an unassuming brick pathway in the middle of the sidewalk, stretching about 2.5 miles through the city. As you follow the path it takes you through 16 historic Boston sites. You can take a more formalized walking tour with a guide, or just do what we did and walk along portions of the trail as we traveled to our next destination, Quincy Market. The trail runs through the middle of Boston and heads north towards the Old North Church, where Paul Revere and his compatriots lit the lanterns to signal the British were coming before his famous ride. The trail then crosses the river where you’ll find Bunker Hill and the U.S.S. Constitution. Read about my experience on a self-guided walking tour of the Boston Freedom Trail for more information.

Quincy Market

We made another stop at Quincy Market to wander the shops and pick up a souvenir or two. We weren’t quite hungry enough for a lunch, but we couldn’t resist stopping at Magnolia Bakery for some sweet treats. The market has both sit down restaurants and food court style vendors with seating. Instead of following the Freedom Trail beyond Quincy toward the Old North Church, we chose to head east along the harbor.

Boston Harbor

Boston may have one of the most famous harbors in the world. Boston Harbor was immortalized with the Boston Tea Party when angry patriots protesting taxation dumped the English tea into the harbor. There is actually a floating museum on replica vessels that commemorate the event if you are interested in learning more about the rebellion. Today, features of the harbor include boat tours and the New England Aquarium.

Cisco Brewery Pop-up

I love finding little pop-ups in cities, and one of the great things about walking the city is that you find impromptu things to do as you walk from one destination to another. On our way to Harpoon Brewery we happened to find a pop-up bar for Cisco Brewery from Nantucket. We grabbed a Whale’s Tale Pale Ale and took a quick break from our quest to go drink even more beverages. The pop-up was not much more than a roped off area with a set of picnic tables and trailers hauling brewery merchandise and taps, but it’s a great way for smaller breweries like this one to get their name out there and maybe find a few new fans.

Harpoon Brewery

After warming up with a beer from Cisco Brewery, we finally made our way through the rest of the Seaport District to Harpoon. One of our favorite parts of the trip was sampling some of their beers and munching on some soft pretzels in the beer hall. We decided to just sit at the bar instead of going through the tour, and I got a flight of UFO beers including a seasonal pumpkin ale, pineapple ale, raspberry ale, and a wheat ale. The place was absolutely packed but we were able to snag a few seats at the right time. If you want to buy a six pack or some merch on your way out, that’s also an option.

Lawn on D

Since Harpoon happens to be pretty close to this little park called Lawn on D (D being the street name), we decided to make a quick stop there to hang out for a bit before dinner. Lawn on D is popular for its circular swings and people actually take turns for a few minutes to lounge around and take pictures on them. I was able to get a couple cute shots with my roommate too!

Mike’s Pastry

Instead of walking, we elected to take an Uber back up to Quincy Market and make our way north up through Little Italy. Boston’s Little Italy is everything you could wish for in an Italian food paradise. On our trip to Montreal, this is the type of Little Italy I was hoping for when walking through that section of the city. In Montreal’s Little Italy it felt like there was a shortage of restaurants; in Boston it felt like food was the entire way of life.

Sprinkled among the many Italian places lie two rivalry pastry shops, Mike’s Pastry and Modern Pastry. My roommate is firmly in the Mike’s Pastry camp, so we elected to stop at Mike’s where the line is continuously out the door to get just one thing- cannoli. Mike’s has a ton of different flavors of cannoli so we got a selection of chocolate chip, limoncello, and peanut butter cannoli. On my next trip I suppose I’ll have to try Modern Pastry in order to best compare which delicious pastry I consider the best.
I’d love to know if anyone has eaten at Mike’s or Modern Pastry and which you liked better!

Dinner at Giacomo’s

Finally, it was time for dinner and we were looking forward to this place all day. Giacomo’s is consistently voted one of the best Italian places in Boston. Their most popular location is just down the street from Mike’s Pastry, but fewer people know that there is actually a second location in Back Bay where we started our journey, so we chose to make our way back towards the car and wrap up our day at this unbelievable restaurant. The restaurant is quite small, but we were lucky enough not to have to face a line like we would have if we stayed at the northern location. If you enjoy spicy food, I highly recommend ordering some pasta fra diavolo as it was absolutely delicious and more than enough food in two plates to satisfy the three of us before heading home.

Boston in 1 Day

This trip was definitely a great way to capture all the major sights and eats of Boston in 1 day. When I get a chance to go back, I’d love to explore more of the surrounding areas and perhaps learn a bit more about the history of the city and marvel at the old architecture.

What else would you add to the list to see in a 1 day Boston itinerary? Check out where we went on the map below.

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