I have visited Boston twice, once with my Mom and Grandmother, where Boston was our first stop before New York City. And then again with my husband, Kevin, where Boston was our first and last stop on our New England road-trip. During both trips to Boston, we stayed 2 days and hit all of the tourist spots. In this blog post I will combine the best aspects of both of these trips to give you the ultimate 2 day Boston experience.

Where We Stayed

On the first trip, we stayed at the Langham, a former federal reserve bank now a historic hotel, on the edge of Boston’s financial district.

On the second trip, we stayed at Boston Park Place, closer to Boston Common and Newbury Street.

Getting Around

On Trip 1 we didn’t bother renting a car because the city is very walkable and uber friendly. On Trip 2, we did rent a car for the remainder of our New England road-trip; however, we didn’t use the car to get around Boston. Take this information as you will, but I wouldn’t recommend a rental car unless you plan on going to some of the places that are located further out on Day 2.

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Day 1

Logistically, I will be sharing this itinerary based on staying at Boston Park Plaza. Leaving Park Plaza, walk along Arlington St towards Newbury Street but pass by and continue on to Beacon Hill, you will hit Newbury Street on Day 2.

Commonwealth Avenue Park is a stretch of park that enters Boston Common in one direction and in the opposite direction, a fun roam of memorial statues. You can find statues of Alexander Hamilton, General John Glover, and Boston Vendome Hotel Fire memorial, just to name a few.

Beacon Hill is one of Boston’s most picturesque neighborhoods with its red brick sidewalks, cobblestoned street, elegant townhouses and gas street lamps. 

Here you will find the iconic Cheers, the bar that inspired the TV Show. Formally known as the Bull & Finch Pub, Cheers opens at 11am daily and you can stop in for a drink, as it is a real bar.

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Acorn Street is my favorite street in Boston. It is very picturesque and is definitely worth a quick visit. On holiday weekends it is packed, so a visit on an off day/ weekend for the best photo opportunities.

After taking in all the cuteness of Acorn Street, head back to Beacon Street and continue towards the Massachusetts State House, you can’t miss its large gold domed top. The State House was built on land owned by John Hancock and is located opposite Boston Common.

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Boston Common, the oldest city park in the United States, dating back to 1634. You can spend hours in the park roaming, picnicking, or exercising. It is also a great option if you have kids as there is a lot of room to run around.

The park also offers swan boats and is home to Make Way for Ducklings Statues, famous bronze ducks created by Nancy Schön located near the corner of Beacon Street and Charles Street. Visiting Mrs. Mallard and her 8 ducklings is one of the top Boston kids activities, but visitors of all ages love the statues.

From Boston Common, you can pick up the Freedom Trail, a two brick path, and follow it through the city. The Freedom Trail is a 2.5 mile trail that leads to 16 historical sites. “Preserved and dedicated by the citizens of Boston in 1951, the Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.”

Follow the Freedom Trail to the Granary Burial Ground,  resting place of John Hancock, Paul Revere, Benjamin Franklin’s parents, James Otis, Samuel Adams, victims of the Boston Massacre, and even Mother Goose! There is generally someone handing out free maps to the burial ground upon entry and asks for a tip upon exit. If you feel inclined to tip no problem, but you really don’t need a map to go through this graveyard as all of the main graves are marked. It’s definitely worth a quick roam though as some of these headstones date back to the 1600’s. 

If you have a sweet tooth like me, you may choose to stop in for a Boston Cream Pie from the Omni Parker House, the original creator of the desert. While I wouldn’t say it was the best I have ever had, it’s worth being able to say you had a Boston Cream Pie in Boston 🙂

By this time we were ready for a beer and a bite to eat, so we headed to Trillium Brewing. It was a beautiful day so we sat on the rooftop and enjoyed a few beers, some fresh oysters, and a charcuterie board. After our small snacks, our stomachs were grumbling, we head over to Row 34 where we had the best warm buttered lobster roll! The restaurant has a cool industrial decor and the food …delicious! We got Old Bay onion straws, more oysters, and shrimp tacos to accompany the lobster roll. I just learned that they have another location in Portsmouth; it is highly likely that Kevin and I will be stopping there when we go to New Hampshire.

While on this side of Boston, you have to check out Harpoon Brewery & Beer Hall. Kevin and I have done quite a few Brewery tours, so we really just spent a few hours trying some of their beers and playing board games.

On our stroll to the Boston Tea Party Ships we stumbled upon Cisco Brewers Seaport. A really chill pop-up brewery at the seaport where they serve their own craft beer, wine, tacos and pizza out of shipping containers. Surrounded by high rises, by the water, it’s a really cool place to spend an afternoon grabbing a drink and a seat at a picnic table. If Kevin and I lived in Boston, we would probably hang out at a place like this after work. 

It wouldn’t be a trip to Boston without visiting the Boston Tea Party Ships. A great learning experience if traveling with your kids. 

An hour tour and a few souvenirs later, head to a must see of Boston,  Faneuil Hall Marketplace,  proclaimed “The Cradle of Liberty” by our nation’s fathers in 1742. Faneuil Hall has various shops, restaurants, and street performances through its cobblestone promenade. Be sure to grab a cannoli from Quincy Market to eat while you explore. 

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When you are ready for dinner, be sure to go to the North End for delicious italian cuisine. Boston’s oldest Italian neighborhood is known for its wonderful restaurants and historic sights. The neighborhood is lined with cobblestone streets, unique architecture and lovely aromas of delicious food.  The Freedom Trail can lead you here as the Paul Revere house and the Old North Church can be found in this neighborhood. Funny enough on both visits we ate at the same italian restaurant. There were too many choices, we were hungry and didn’t want to wait so we picked the first restaurant we saw. The food wasn’t bad but we would have liked to have tried any of the following: Giacomo’s, Carmelina’s,Taranta, or Neptune Oyster.  

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Regardless of where you decided to have dinner be sure to save some cash and leave some room for dessert because Mike’s Pastry is just around the corner! Mike’s Pastry is a cash only establishment that has various flavors of cannoli’s and other delicious italian desserts. I know you may have grabbed a cannoli earlier from Quincy market, but in my opinion, you can never have enough cannolis.

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Day 2

Start your day with a stroll down Newbury Street, a 2 mile stretch of elegant shopping, funky salons, and trendy galleries. Even if you don’t find something to buy it’s cool to see the architecture of the street and go into brick and mortars of primarily online establishments, like allbirds. Being from Maryland, Georgetown Cupcakes is a staple… well guess where you can get Georgetown Cupcakes?! 

Follow Newbury Street to its end and make a stop at the Mary Baker Eddy Library Mapparium where you can walk through a three story stained glass globe that has been in the making since the 1930’s. It’s definitely a cool stop. The tours run every 20 minutes and only last about 15-20 minutes starting at 10:20am until 4:40pm. Admission is low cost ($6).

After walking through the world, continue on to Fenway Park. Fenway offers tours every hour on the hour between 9 am and 5pm, except for on game days when they are offered from 9 am until 3 hours before game time. If there is a game that day, perhaps you want to line your tour up with the games start. 

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If you aren’t going to stick around for a game, grab an uber and head to Cambridge where Harvard University is located! 

I have always loved touring different campus’ and I used to collect t shirt from every single one. As you can imagine, my t shirt collection got quite large so I have had to tone it back since. Harvard, however, holds a close place in my heart. Ever since Elle Wood’s, played by Reese Witherspoon, went to Harvard to become a lawyer in Legally Blonde, I told my parents I was going to Harvard Law School too. A lot had changed before I graduated high school and instead I had decide business and travel were my passion. Therefore, I went to the University of North Carolina Wilmington and got a degree in International Business. While I am sure my parents were happy that I saved them a buck or two, that childhood dream is still alive in both my mom and me. To this day you may catch me in my Harvard t shirt or tank top or drinking tea out of my Harvard mug, like I am right now. 

Harvard’s campus and the architecture is beautiful. Cambridge is a small town that surrounds the campus and has anything you could want. The town actually reminded me a bit of Europe, at schools like Cambridge or Oxford. Definitely a cool place to spend an hour or two. I have never been but have heard great things about Cuchi Cuchi. It was described to me as a very girly restaurant where the servers wear costumes from the 1920s and 30s, serve vintage cocktails and tapas from around the world. If you go, you will have to tell me if fits its description. If you are looking for something a little more casual, and perhaps a laugh or two, check out another staple of Cambridge, Massachusetts,  Mr.Bartley’s Gourmet Burgers.

After lunch, if you are in the mood for some Boston born and bread brews, Sam Adams Brewery might need to be your next stop. Take a brewery tour if you want and be sure to visit the tap room. 

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New England Patriots Fan? Gillette Stadium  is 20 miles south of the brewery. The stadium does not offer tours, but you can browse the shops and restaurants, go bowling, or play top golf at Patriot Place. Every Patriots fan should visit the Pro Shop and the Patriots Hall of Fame. 

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Whether you are just going to Boston or doing a road trip through New England, I hope this blog helps you make your plans! Give me some feedback, what did you like? Did you try any of the restaurants I recommended? How were they? All in all, I hope you enjoy your trip!