East Coast

How to Spend 2 Days in Boston

In 2017 we set out to the East Coast to find ourselves the most beautiful leaf peeping and season changing we could find. We embarked on a 9 day road trip through the New England area, which include the states of Massachusetts, New Hampshire, Maine, Vermont, Connecticut, and Rhode Island. We spent time in every one except for Connecticut and since it’s the fall time again, it’s only fitting to start our posts on this area. It was one of our favorite trips we’ve ever taken, given the immense American history, the brew tour, and the sense of community that New England exudes.

In this post, we’re going to be focusing on Boston, the first stop on our trip. We spent two full days in Boston and one half day on the back end of the trip before flying back out to Reno.

Pro Tip:

When flying into Boston from the East Coast, try to find yourself a red eye flight. That way, you get into Boston in the early morning with a full day ahead and get a little sleep on the plane! Double bonus when your hotel or airbnb lets you drop your bags for the optimal adventuring!

Don’t forget to watch Good Will Hunting before your visit, that way you can get your best Boston accent on while in the city.

getting around

The public transportation in Boston rivals that of our favorite European travel – reminding us of the high tech travel of Vienna. It is easily the best way to get around in the city – there is no need for a car, in our opinion. Their subway system, nicknamed the T, is 100 times better than the New York subway. We never had any problems figuring out the different colored lines (there are 5) or any delays, although we can’t promise they don’t happen!

Pro Tip:

If you’re going to be in the Boston area for more than two days or know you are going to rely on the public transportation, we recommend you buy the Charlie Card. It is basically a rechargeable ticket that allows you unlimited access to the subway, bus, commuter rail 1A, and the Charlestown Ferry for either 1 or 7 day increments. Since we knew we’d be relying on the subway we went with the most cost effective way to get around, the 7 day Charlie Card. Considering that one ride on the subway is $2.25, the $21.25 Charlie Card gave us peace of mind that we wouldn’t have to worry about going over 9 rides on the public transpo. Grab yourself an MTBA route map and enjoy being a local on the subway!

where to stay

We decided on an Airbnb in Davis Square area, in the borough of Somerville. We wanted to stay in more of a neighborhood rather than the inner downtown area of Boston so we could get a more authentic Bostonian experience. You can check out our specific Airbnb here, a two bedroom upstairs private apartment with a shared bathroom. We really loved our neighborhood and felt like it was still very central to everything in Boston that we wanted to do. We were a block away from a station on the T and had great options for food and drink.

when to visit

We chose the first week of October to visit the New England area so we could see the changing of the season. For most of the days we spent in Boston, we got dry weather with a hint of rain on the very last day of our visit. We hear the winters can be pretty brutal and last into the spring season. On the flip side, the summers can be fairly humid and full of all different kinds of weather.

things to do

One of the biggest draws of Boston is its rich history and preserved monuments, but there is also a certain modern cultural draw to the city. In our opinion, Boston is a more local, cozy New York City. We love both cities but Boston has an air about it that makes you feel like you’ve just stepped into the normal routine of the locals. You can feel less touristy in this city, which is something special we think. Here are some of our top activities to experience in Boston!

Freedom Trail

The Freedom Trail is a must for first time visitors in our opinion. It is a 2.5 mile red brick trail that winds all around the city, taking you to the most historic monuments of Boston. There are many options to do a guided tour or a self guided tour to take things at your own pace. We chose the self guided option and chose an online video guide at Free Tours by Foot. They offer a one minute video on each stop, giving you the quick basics so you can continue on to the next stop in a timely manner. You will definitely want to plan an entire day for the Freedom Trail, especially if you’re like us and you want to stop along the way to get food or drinks. Either tour you decide on starts at Boston Commons (the oldest park in the US!) and continues all the way across the river to the neighborhood of Charlestown. Here are some of our favorite spots along the way.

Boston Common

This is the oldest public park in the US and the center of the happenings of the city! It’s important to note here that Boston Common is a singular term – it’s Common not Commons!

(New)State House

The New State House was put into service in 1798 and happens to be the oldest continually running state capital building in America! Plus – check out that 23k gold dome! You can take a free guided tour of the State House during the weekdays but you’ll have to call in advance if you want to get a spot.

Granary Burial Ground

This little cemetery packs a big punch, it’s where a lot of famous Bostonians are buried – including 3 signers of the Declaration of Independence, Paul Revere and the parents of Benjamin Franklin!

Old State House

The Old State House is a very important monument in Boston. This is where the Declaration of Independence was first proclaimed and the patio in front of the State House is where the Boston Massacre occurred. Every 4th of July, the Declaration is declared on the balcony of the Old State House for locals and tourists alike!

Faneuil Hall

Nicknamed the “Cradle of Liberty”, Faneuil Hall is a very important part of Boston’s history. This is where copious amounts of meetings, speeches, and protests happened to kick off the American Revolution. Just as it was back then, there is a market hall on the bottom floor and the top floor holds the grand meeting hall.

Paul Revere House + Statue

As you make your way to the North End, you will come into our favorite neighborhood of Boston – Little Italy! We had the best food and drinks in little Italy and it has the all around Boston feel we were looking for. Also in Little Italy is the oldest building in Boston, the Paul Revere house. He lived here from 1770 to 1800 and for $3.50 you can go inside and get a glimpse of his life. Just a little further on the Freedom Trail you will find the actual statue of Paul Revere, in front of the Old North Church that he famously lit up to warn that the British were invading.

Copp’s Burial Ground

This is the second oldest burial ground in Boston, but doesn’t hold as many affluent Bostonians as the other cemetery’s do. There is still some notable people to see but we liked it because of the quiet hill in the North End that the cemetery sits upon.

USS Constitution + Cassin Young

When you cross the bridge into Charlestown, you’ll come to your second to last stop on the Trail – the Navy Yard. Unfortunately we didn’t get to actually go onto the USS Constitution, the oldest ship in the US Navy. It was dry docked and unable to be toured due to reconstruction when we visited. However, we did get to head aboard the USS Cassin Young, a navy ship that fought in WWII and the Korean War. You can also visit the interactive USS Constitution Museum on the same grounds as both ships to learn more about the ship’s history.

Bunker Hill Monument

The final destination of the Freedom Trail is the Bunker Hill Monument, where the Battle of Bunker Hill took place. You can ascend the 294 steps of the tower to get a 360 degree view of Boston and Charlestown. At the base of the hill, you can find a museum to learn more about Bunker Hill and the 1775 battle.

Fenway Park

No trip to Boston is complete without a trip to Fenway, hands down. It is the oldest Major League Baseball stadium and rife with history. If you visit during the latter end of fall, you’d better hope that the Red Socks have made it to the playoffs. Their regular season happened to still have one more game during the week that we were in Boston so we got to experience a game! Any area of the stadium will give you a great view of the field, but we chose some seats behind second base that just happened to be in the sunshine during our game. It was GLORIOUS, we even had to buy sunscreen from one of the shops! And, you can’t go to Fenway without eating a Fenway Frank – the ballpark’s hot dog.

Even if you’re not in Boston during baseball season, you can still take a tour of Fenway any other time of the year. We think it’s worth a visit regardless!

Walk the grounds of Harvard

Grab yourself a cup of coffee and head up to the Cambridge neighborhood to walk the grounds of Harvard. There is actually a free student led tour that takes you through the history of the university and daily life at Harvard now. We didn’t do a tour, but did a self guided walk through the beautiful campus grounds. Whether sun or rain, a stroll around the historic brick buildings is a great way to start your morning in Boston.

Tea Party History

Besides the Boston Massacre and the Founding Fathers, the second thing that probably comes to mind historically when you think of Boston has to be the Boston Tea Party, right? Maybe that’s just us. I was dying to learn more about the Boston Tea Party and if the harbor that had tea thrown into it so many years ago was the same one we can see today. I am here to tell you – it absolutely is!! Same water, slightly different harbor. We found the Boston Tea Party Museum in the Boston Harbor that offered up a perfect glimpse into this history. Boston was built back up a little differently than when the patriots made their statements in the harbor, but it is still the same water that flows under the museum. The Tea Party Museum is an interactive and fun way to learn about the tea party history and you even get to throw a box of tea overboard a replica ship! In our opinion, you should make it a point to visit and learn the history of the early Patriots in Boston and why they held this issue so close to their hearts. 

Sam Adams Brew Tour

Unfortunately, we didn’t get to actually do the tour of the brewery when we made it to Sam Adams. We weren’t able to make it on our first two days in Boston so we had to try to fit it in to the half day we had before we left. The times of the brewery tours sell out FAST and since we were a little late on the draw, we had to be back to the airport before the next tour started. However, we were able to grab a drink in their outdoor patio and pick up a couple souvenirs in the gift shop before leaving. If you absolutely want to see the production of Sam Adams (and enjoy a free flight of beers!), we recommend getting there early and giving yourself extra time in case your first option for a tour time is booked. The tours run on a first come, first served basis every 30 minutes, but it is likely you may not get the tour time you want if you are late.

Acorn Street

This is quite possibly the cutest street in all of Boston. We saw this online and just happened upon it on our way to the Freedom Trail start while we were exploring the Beacon Hill neighborhood. There are loads of reasons why this little street is so special, but the biggest one is because it’s one of the only places that still has actual cobblestone streets. You get a cool glimpse of what  colonial Boston was like and even though Acorn Street is just a small street, the whole Beacon Hill area should be explored!

Day Trip to Salem

We decided to just spend the day in Salem after we picked our rental car up to head north into Maine. Since we didn’t have much to see in Salem, we had breakfast and explored by walking around the “downtown” area. We think it’s worth it to see the cemetery, hit up a witch’s museum, and get some grub at Red’s Sandwich Shop.

where to eat + drink

Diesel Cafe – If you find yourself in the Davis Square area, this was our go to coffee spot and should be yours too. They have craft specialty coffee, fresh baked pastries, and a small but delicious breakfast menu. Plus, they are open until 9:30 pm in case you need a caffeine fix to get you through a long day. The staff wasn’t the most friendly but what etiquette they lacked, they made up in flavor.

The Burren – Also located in the Davis Square area, this traditional Irish pub was where we found ourselves both nights we spent in Boston. It reminded us a lot of some of the Irish pubs we visited in Dublin, complete with a live band both nights we visited. The food was delicious and it was our first experience with Irish coffees so we’d say The Burren is a success.

Warren Tavern – We think this should be a must visit if you find yourself at the end of the Freedom Trail and want a place to eat or drink in Charlestown. Built in 1780, Warren Tavern was the first tavern in Massachusetts and frequented by George Washington and Paul Revere. It was also our first experience with a CINNAMON SUGAR RIMMED glass of Shipyard Pumpkin Ale and it was AMAZING. It’s a very historic restaurant and their food is amazing so make sure you stop in – if for nothing else than a glance back at where our founding fathers ate and drank.

La Famiglia Giorgio’s – Located in the North End or Italian District, this amazing family run restaurant CANNOT be missed. We asked a few people in the neighborhood where their favorite place in the Italian district was for authentic Italian cuisine and we found ourselves at La Famiglia based on those recommendations. We recommend coming with a full appetite because the portions here are insanely huge and filling. Try not to eat all the bread before your meal but definitely try any of the recommended wines from their cellar.

Mike’s Pastry – There was  C R A Z Y hype about Mike’s Pastry from everyone who had visited Boston before us. We finally made it to grab a pastry here on our last few hours in Boston and I’ll be honest when I say I wasn’t going to put too much pressure on Mike’s just in case it didn’t live up to the hype. BUT, it did. And the Boston Cream Pie we stood in line for and took boxed up to go, it delivered. Don’t be intimidated by the out the door line, it goes by quickly and the employees of Mike’s have got down a good system. However, don’t be scared to push your way to the counter and put in your order! Although they make so many amazing looking desserts, we recommend the tried and true Boston Cream Pie or the famous cannoli in the famous bow wrapped white box before your departure.

The Tip Tap Room – Before you start your tour of the Freedom Trail, make sure to fuel up on brunch at the Tip Tap Room. We love ourselves a good Bloody Mary in the morning, so we sat at a window seat and enjoyed the house made Tip Tap Bloody Mary to kick start our day. Although we didn’t eat here, the smells and sight of their Eggs Benedict was enough to make the fullest of bellies hungry again!

Granary Tavern – If you need a quick drink before you head to the airport, the Granary Tavern is your place to hit up. Located in a building from 1816, they have all the local beers on tap and an extensive and unique food menu, although sadly we didn’t get to eat anything. The ambience and location alone are worth the visit.


We could have spent an extra few weeks in Boston to explore more of its charming neighborhoods and one day we will definitely go back to find more hidden gems. Anything else we missed that we have to add to our list the next time around? Let us know in the comments below.

We’ll see you next time for the second stop of New England 2017!

xoxo,

The Traveling Tavener’s

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