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Planning a Trip to Boston? Here Is What I Did for 5 Days


Get an extensive list of things to do in Boston. You'll find a mix of well known and not so well known attractions to visit and loads of pictures.

Quick Jump: Getting From New York to Boston | Where Will You Sleep, AirBnB or a Hotel? | Now the Fun Part, Figuring Out What to Do for 5 Days | Copley Square and the Boston Public Library | Soaking in the Town on the First Day | Boston Museum of Science | DCR Hatch Memorial Shell | Boston Public Gardens | Boston Commons | Faneuil Hall / Freedom Trail | North End | Christopher Columbus Waterfront Park | Long Wharf Ferry Port | Charleston Navy Yard Museum | Bunker Hill | Harvard Campus | Harvard Museum of Natural History | Harvard Peabody Museum of Archeology and Ethnology | MIT Campus | Back Bay Love Locks | Mapparium | Google Map Coordinates

I’m dabbling with the idea of doing long term travel in the future, so I decided to visit Boston Massachusetts for 5 days as a test run. I went in the middle of June 2016.

If you’re interested in only pictures, here’s a gallery with over 400 pictures.

Getting From New York to Boston

99.9% of this article will be about Boston but it’s worth noting that if you live on Long Island like me and you want to take the train then you will very likely want to take the ferry over to Connecticut first.

Once in CT you can take an Amtrak train up to Boston. The Amtrak line runs from Penn. Station in NYC too, but from CT it’s 1.5 hours less time. If you’re in the middle or east end of Long Island then you save yourself a trip on the LIRR too.

In my specific case it took 1 hour and 15 minutes to go from Port Jeff to CT by ferry, then 3 hours by Amtrak from CT to Boston. The ferry drops you off in Bridgeport, CT and the Amtrak station is a 3 minute walk.

If you’re on the east end of Long Island you can take the Orient Point ferry to New London instead. In this case, it will be way faster than taking the LIRR to NYC.

If you book your tickets 2 weeks in advance it will only run you about $49 each way. The ferry from Port Jeff is $34 for both ways. The LIRR is $26.50 for off peak rates, so really you’re paying $8 more to take a ferry ride and save yourself roughly 2 hours of travel time. Totally worth it.

Where Will You Sleep, AirBnB or a Hotel?

I have never used AirBnB but I decided to try it. Downtown Boston was pretty expensive. If you go the hotel route, expect to pay about $200/night.

AirBnBs in downtown Boston were around $150/night too.

I decided to shop around for places near Boston and went for a 1 private bedroom house in Everett. The public transportation near Boston is pretty reasonable.

It was a 30 minute bus ride to downtown Boston and the buses all have air condition which is a plus, especially when it gets packed in.

I stayed at this place for $37/night at the time of booking it.

It was a nice little room and the hosts were very cool. They stayed in the house with me but I had a private bathroom. I actually left a review of it on the page linked above if you want to hear my opinion on the place.

Now the Fun Part, Figuring Out What to Do for 5 Days

This is the fun part, at least it was for me. I had no idea what to expect from Boston but since I’m a software developer, I’m used to doing research.

About a week before the trip I spent a solid day just looking for things to do in Boston and eventually came up with a list.

I like the idea of preparing for a trip, but I don’t like the idea of set schedules. If you try to go on a trip and plan things out to the exact minute or hour then it’s going to end up feeling like work and you won’t have fun.

My approach was to come up with 15 things to do, and then do them as I went. I didn’t know the order I was going to do them in until I was there in Boston.

Definitely Pay Attention to Hours of Operation

When researching things, it’s important to take note of when the attractions you plan to visit are open. This isn’t obvious, even though it seems like it would be.

Take Advantage of Public Transportation Passes

There’s this thing called the “7 day Charlie Pass” and for $19 you get unlimited bus, subway and inner harbor ferry rides.

If you plan to stay for a number of days it’s totally worth it. Even if you only took the bus from your room to downtown Boston twice a day for 5 days you’d come out ahead by purchasing the weekly pass.

By the end of my trip I calculated that I used $38 worth of public transportation but I only ended up spending $19 on the pass.

Pre-Load Everything Into Your Phone

I don’t even have a smartphone (I’m serious), but I caved in and bought a $40 Samsung Stardust through TracFone just for the trip.

Then I topped it off with 180MB of data and 180 minutes of calling for $20. I didn’t care about calling, but it came included with the data plan.

Having access to Google Maps is very useful if you’re in a new town. I feel like I could have survived without it, but I would have had to print multiple maps and also manually figure out the bus schedules.

If I had to do it again, I would totally bring the smartphone again. I was also really surprised how efficient Google Maps was. It only used 23MB of data after 5 days of heavy location based GPS tracking.

Anyways, you should definitely star / label all of the places you plan to check out because then it’s super simple to get to / from directions.

Copley Square and the Boston Public Library

My train dropped me off in the Back Bay station which is in a great location in downtown Boston. It was only a 3 minute walk to Copley Square and the main Boston Public Library.

The bus station to get to my AirBnB was a 30 minute walk from here but that was perfect after sitting on a train for 3 hours.

I was blown away at how clean Boston was. Seriously, I would have felt comfortable walking around most of the entire downtown area barefoot.

The sidewalks and streets were in excellent shape with no garbage to be seen.

Soaking in the Town on the First Day

I spent most of the first day just walking around town aimlessly because I arrived in Boston around 2pm.

That was a bit too late to hit up any main attractions, but still early enough to have a great day so I walked around town for a few hours with my only piece of luggage which was a 15 pound backpack.

By around 5pm I decided to head up to the AirBnB. I unpacked and then walked around Everett for a while. There’s a few pictures of that in the photo gallery I set up for the trip.

By around 8pm I was pretty shot. I was up the entire night beforehand because who can sleep the night before a trip? Also I had left my place at 7am.

I got a chance to meet my AirBnB hosts that night and we talked for a bit. Unfortunately I couldn’t sleep much that night because I’m weird when it comes to sleeping in new locations.

I eventually fell asleep around 4am, but at about 5am I woke up with one of their cats sniffing my eyeball. Yep, that freaked me out. That’s when I learned that cats can open doors.

Boston Museum of Science

Despite not sleeping much I wasn’t tired, so I left the AirBnB pretty early.

After hitching a ride to downtown Boston on the bus I walked over to the Boston Museum of Science which wasn’t too far at all.

The place was massive. I haven’t really visited any museums so I wasn’t sure what to expect. I was blown away at how many exhibits it had and how efficient the building was laid out.

The museum covered a lot of different topics. You’ll see insects, dinosaur bones, human anatomy, rocks, nature, machines and so much more.

I was able to spend 6 hours there without trying and I didn’t even goto most of the paid events. That was time spent only in the open exhibit halls.

I highly recommend spending the extra $6 to visit the planetarium. I ended up seeing the universe show and it was well worth it. It’s also worth checking out the lightning show in the exhibit hall which is a free event that runs every few hours.

Before leaving the museum area, make sure to cross the Charles river. There was a nice little park to walk around and it only took a few minutes to get there.

DCR Hatch Memorial Shell

I decided to walk down the Boston side of the Charles river from the Museum of Science and came across this place. I didn’t plan to visit it, but it was pretty nice.

Supposedly the town puts on a lot of events here, but nothing was happening at the time of my visit.

By the time I made my way here I was ready to get dinner. If you were to turn around in the above picture, you would see the Charles River Bistro.

This was a casual place to get lunch or dinner. It reminded me of a beach shack.

I ended up getting an angus burger and a fruit cup for about $7. Not too shabby. The service was good and it was enjoyable to eat dinner outside near the water.

Boston Public Gardens

Next up I headed over to the Boston Public Gardens. It is well known for being in immaculate condition and for hosting various events.

I’m not really someone who is into flowers or gardening but I can appreciate the workmanship that was put into this place.

It ended up being a really enjoyable park to walk through and had monuments to look at such as George Washington (check out the full photo gallery).

Boston Commons

Right next to the garden are the Boston Commons. I don’t know the exact cut off line but I think it’s Charles St. which splits the 2 landmarks in half.

It’s another well kept park that’s quite a bit bigger. You’ll find people playing frisbee, bean bag tossing and other games in this vast open space.

Unlike the garden, you’re allowed to go on the grass here.

If you want to get a map of the city or look for tourist attractions this is the spot to visit because it’s where the Boston Common Visitors Center is.

Faneuil Hall / Freedom Trail

This hall is interesting because it’s where you can sign up for the freedom trail that runs through out the city.

These are 1 hour walks around the city where you can get a guided or unguided tour of famous historic landmarks.

There’s a few different trails. I took the one that ended with the Boston tea party.

The guided tour is normally a paid event but if you go inside Faneuil Hall you can sign up for a free guided tour with a park ranger.

I decided to do that and it was worth it because the ranger giving the tour has been trained for public speaking. She made it very entertaining and even got the crowd involved for some of the tour.

I learned a lot, but honestly it was super interesting to me mainly because as a content creator myself, I got a lesson on how to improve my delivery by watching her work the crowd (we went out with about 30 people).

North End

The North End section of downtown Boston is famous for having some of the best Italian food in the country. It’s also where Paul Revere’s house is.

It’s an upscale neighborhood with very narrow streets and red brick buildings.

My fingers got jealous, so I made sure to include them in this picture.

I didn’t end up eating anywhere here but I did explore the whole area. It was an interesting zone because it felt like I was transported to a different time.

The outskirts of North End had a few really nice views on the water too.

Christopher Columbus Waterfront Park

I didn’t spend too much time here but it was worth checking out mainly because it’s on the way to the Long Wharf ferry and the water views were fantastic.

If you’re into history then you’ll certainly want to check it out.

Long Wharf Ferry Port

This is the entry point to take a ferry over to the Charleston Navy Yard. It’s a free trip if you have the 7 day Charlie Pass and it only takes about 10 or 15 minutes.

I really enjoy port towns. There were so many people just hanging out:

The ferry ride was smooth and offered awesome views from the top of the boat:

If you’re lucky, you might even see a pirate ship:

Charleston Navy Yard Museum

This place was pretty interesting. Not only did it have an indoor museum but it also has 2 large ships outside that you can board.

The museum wasn’t massive but it’s worth checking out. You’ll get a real idea of what it was like to be a sailor a few hundred years ago.

I wouldn’t consider myself someone who is really into Navy history but I had a really fun time at this museum and learned quite a lot.

USS Constitution

This is a ship that you’re allowed to board, but be warned that you will need to empty your pockets and put all bags through a scanner before being allowed on.

This precaution is mainly because it’s still in commission.

Once aboard you can explore above and below deck. There’s even a Navy crewman who will give you a brief history recap of the ship.

USS Cassin Young

This is a destroyer ship that I’m pretty sure you’re allowed to board normally. Sadly it was closed at the time I went, but I did see welcoming bridges to go on. Perhaps it was just too late in the day when I went.

I would have liked to walk on it – maybe next time!

USS Boston

The last main attraction to see are the guns at the end of the pier. Not only is there history behind them but it offers a nice skyline view of the city.

Bunker Hill

If you’re up near the Charleston Navy Yard Museum then you should definitely check out Bunker Hill as it’s only a short walk over to it.

You can even climb it. It’s a steep 254 steps up but be warned that you can only climb it during certain hours.

At the time I went the last climb was 4:30pm which I didn’t know beforehand. I ended up missing it by 20 minutes. Maybe next time!

It’s still a very cool piece of history to check out regardless of the climb. The monument is so tall once you get to it.

I never knew William Prescott looked like such a bad-ass.

Harvard Campus

Next on the list was Harvard which is located in Cambridge. It’s a short subway ride on the T line from downtown Boston.

I recommend carving out a full day if you plan to go here because there’s an excellent museum to visit and MIT is also very close which is worth checking out.

The Harvard area itself has a lot of interesting architecture.

You’re allowed to walk around the campus. I found it to be hilarious because I saw roughly 50 million tourists walking around taking pictures.

I even overheard others saying things like “I can’t believe how overrun this place is with tourists. I would never pay to goto school in this atmosphere”.

I have nothing against tourists but it was funny to me because I envisioned the campus as a really exclusive and upscale place.

I thought girls would be sitting outside drinking tea with their pinkies up while guys played badminton in their sweater vests.

Harvard Museum of Natural History

I almost didn’t goto this museum because I thought it was free due to an event that was going on, but it wasn’t.

I’m really happy I talked myself into dropping the $12 to go in it because it was epic. It was much different than the Boston Museum of Science.

There were all sorts of pre-historic animals and stuffed life sized versions of them. Getting to see a siberian tiger up close blew my mind. It was about 12 feet long and its paws were large enough to rip your face off in 1 swipe.

If you’re into rocks and gems you’re going to love this place too. There were so many interesting things to look at.

There were also exhibits on human history. I came across a weapon rack here that reminded me of an old game I used to play called Diablo 2.

I took over 100 pictures of this place, so make sure to check out the photo gallery. I spent around 2 hours there without breaking a sweat.

If you go there, make sure to check out the glass flower exhibit. I didn’t take any pictures because no flash cameras were allowed.

It was an incredible place to visit. The flowers were all made of glass but they looked natural. There’s no way you would have been able to tell without knowing beforehand.

Harvard Peabody Museum of Archeology and Ethnology

This museum is across the street from the Museum of Natural History and it’s free admission. It’s very small but worth checking out while you’re there.

You’ll gain insight on ancient Egyptians and other civilizations.

MIT Campus

MIT is very close to Harvard so definitely plan to check both of them out in 1 outing if you’re interested.

You can go by subway or take the 2 mile walk. I ended up taking the subway because I was pretty pressed for time. At this point it was around 4pm and I had an Android meet-up in downtime Boston at 7pm.

The MIT campus had a lot of interesting architecture. For example, here’s the buildings that house its data center.

There were dozens of buildings and things to explore. I recommend going to the visitor’s center and either taking a guided tour by one of the students or taking the self guided map tour.

Since I got there so late I did a brief self guided tour but only got a chance to explore a tiny fraction of the campus.

Make sure to check out the infinite hallway. It was a massive indoor hallway with a lot of interesting things to look at as you passed various rooms.

There were much less tourists here and it really felt like a legit campus.

Back Bay Love Locks

While heading to my final destination of the Mapparium in downtown Boston I came across a pretty cool bridge. I had no idea this existed until I walked past it.

I wouldn’t say I’m a padlock enthusiast but it was really interesting to look at up close. There’s so many different lock types and I’ve never seen anything like it.


One of the last things on my list was to check out the Mapparium. It’s this really neat planetarium-like structure to look at.

It’s a 3 story stained-glass globe that shows the world as of 1935. You get to walk inside of the room on top of a transparent bridge and a guide explains the history behind it, and how the world changed over the years.

Unfortunately they were very strict about taking photographs but you can find some on their official website.

The acoustics in the room were incredibly creepy. You could stand across the bridge and hear someone whisper from the other side.

Also if you stood in the middle of the room you could hear sounds bounce around from everywhere because the curved glass walls reflect sound back rather than absorb it. You really have to experience it first hand.

The below picture is a neat fountain in the lobby area where a projector displays words onto moving water.

Google Map Coordinates

Here’s Google Map coordinates for everything I talked about above and more:

Boston was a great trip and I highly recommend that everyone checks it out at least once in their life time if they enjoy cities or any place near water.

I am curious to hear what places you saw in Boston because I am very confident that I’ll be going back at some point in the future.

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