Summer in Boston: A 4-Day Itinerary

Boston Skyline

In the summer of 2018, we decided as a family to head to Boston. Home of the Boston Marathon, Fenway Park, Harvard (actually in Cambridge), The Freedom Trail, and many many more historical events.  Again, being big movie buffs, we tied in seeing movie location spots of some of our favourite movies.

Boston is actually the capital of the world.  You didn’t know that? We breed smart-ass, quippy, funny people….. John Krasinski.

Our ‘Must-See’ TV/Movie Location spots and Tourist Area Locations:

  • Cheers Bar
  • Boston Common Park (bench in Good Will Hunting)
  • Harvard University (Good Will Hunting, With Honours, Legally Blonde)
  • Boston Marathon Finish Line (Patriots Day)
  • Quincy Market
  • Harbour Front Area
  • Freedom Trail
  • Cirque du Soliel – Luzia (pre-booked prior to arrival)
  • Salem – to learn about the Salem Witch Trials

Our 4-Day Itinerary included arriving on Saturday at Boston Logan International Airport.  We flew from Syracuse straight to Boston arriving first thing in the morning at 6:30am.  I had arranged to travel by subway/transit  – the MBTA – to the Beacon Hill area where our hotel was located.  It is a super easy system to use. We purchased a 7 day pass for each of us (we are a family of 4). This was a cheaper way to  go since it gave us unlimited access on and off during our 4 day stay.  The system is all colour coded, so you can easily disifer which subway to choose.    

We stayed at the Wyndham Boston Beacon Hill Hotel.  We chose this hotel due to its close proximity to the multiple subway stops, walking distance to the Harbour front and Boston Common Park, the commuter train for out of town excursions, as well as located within old Beacon Hill with cobble stone streets and adorable shops.  It also had a roof-top pool, which was a bonus.  We wanted each step of our 4-Day adventure to be seamless with travel options right at reach.  We certainly achieved that.  How did I find such a great hotel?  I found it on  It’s a fantastic site with countless hotel and accommodation options.  

Day By Day in Boston


We arrived bright and early due to our 6:00am flight from Syracuse, NY.  But!  No problem at all.  The team at the Wyndham took care of us. We did a pre-check in and they took my phone number in order to call us when our room was ready.  They stored our luggage and even suggested a quaint spot to eat breakfast in.  

We then began our exploring.  We walked the cobble stone streets and found Acorn Street; the oldest street in Boston and made our way to Boston Common Park.  We were excited to find the bench that was filmed in the movie “Good Will Hunting”.  We also found many brownstone type homes with colourful doors.  I love bright coloured doors and I try to find some in any location we travel to.  

We then headed to find the Boston Marathon finish line.  The streets throughout Boston are magnificent.  It’s a bustling city, but with a small town feel and once we found the marathon finish line, I must say, it was quite emotional.  Knowing that a terrifying act occurred here years prior and standing in the footprint of the site seemed surreal to us.  It is such a compact area filled with businesses, stores, streets and people.  The devastation those bombs caused not only to the victims, their families, the marathon and the spectators, but also to the business and storeowners.  It was a moment, we would never forget.

Side Note:  We actually have friends who were part of the marathon staying at the hotel adjacent to the finish line.  They had just finished their run and had to evacuate immediately and run as far as possibly away from the site – any movie based on the marathon and in real TV footage you will see a Canada Flag hanging in the window – that was their room.  

We were starting to get hungry, so off we went to locate the famous ‘Cheers’ bar.  My husband and I grew up watching the TV show Cheers and loved it.  We could not be in Boston without experiencing the actual pub it was based off of.  We waited in line – only a short while- and stepped inside.  It was packed.  We were unsure where we would be seated and how long we would have to wait to be seated.   The Bar Hostess called our name and we were then taken to the ‘Set Bar’ floor to be seated. This floor had the actual bar that was used in the TV show as the main bar in use.  We couldn’t have been more thrilled.  Again, an experience we won’t forget.

Our room was now ready, so we headed back to the hotel to check in, unpack and relax a bit.  Our room was a standard 2-bed room, but plenty big enough for a family of four.  Since it was very hot out, we decided to head up to the rooftop pool to cool down and relax a bit before heading down to the Harbourfront area/Quincy Market.  

We decided to walk to the Harbour front area.  It looked to be about a 10-15 minute walk.   We took in all the local sites along the way and we fell upon a Puerto Rican fair.  We loved it.  Food, rides, and music.  Such fun.

We made it to Quincy Market and the streets were filled with Buskers, more music, booths filled with crafts, clothing, and souvenirs.  A definite must see to be fully immersed in the Boston culture.  

Right next to Quincy Market is the Harbour front.  Stunning!  Yachts and sailboats and fabulous restaurants along the water, even an aquarium (however, we did not get a chance to see that).  We were fortunate enough to get a table facing the water to enjoy our first dinner in Boston at the fabulous Joe’s American Bar and Grill.  I highly recommend this restaurant.  Not only is their food fantastic, but if you can be seated with a view on their patio, the ambiance with the water is perfect.  

Summary of Day 1:

  • Arrived in Boston at Boston Logan International Airport
  • Check in to the Wyndham Boston Beacon Hill Hotel
  • Explored Beacon Hill, Boston Marathon Finish Line, Cheers Bar, Boston Common Park, Quincy Market, Puerto Rican Fair, Harbour Front


We decided to let the kids sleep in a bit while we went across the street to Starbucks.  My husband loves sailboats and while at the waterfront the previous night, we saw Tall Ship Boat Cruises by Liberty Fleet. We searched their website and booked a time for the day.  We were so excited. 

Our day began with exploring the Freedom Trail and the oldest cemetery in Boston.  Again, filled with cobblestone streets, cute churches, Paul Revere’s House, Clough House – where actor’s portray the colonial times and offer chocolate making demonstrations, Old North Church where the famous signal “One if by land and Two if my sea” is said to be have been sent, and gorgeous architecture.  To really immerse yourself in Boston’s history, this is a must see area. 

We then walked to the Harbour front to embark on our Tall Ship Harbour Cruise with Liberty Fleet around Boston Harbour.  Amazing.  Not only is the view out of this world, but you can actually help if you want to.  My husband and son got to help put up the sail and steer the ship. An experience neither of them will forget.  

After eating a fantastic Lobster Roll lunch at Tia’s, we headed to the transit system for our journey to Suffolk Downs – the location of Cirque Du Soleil – Luzia. The  transit system is so simple to use. The maps are colour coded depending on where you want to go and easily marked.  We got off at our stop and walked to the ‘Big Tent’.  

The show was fabulous.  It was my second Cirque show to see and it did not disappoint!  If you ever get the chance to see Luzia, go.  You will love it.

After the show, we headed back to the transit location and we were able to go all the way to the subway stop – Bowdoin – a couple blocks from our hotel.  So easy.  A great second day.

Summary of Day 2:

  • Freedom Trail
  • Tall Ship Boston Harbour Cruise with Liberty Fleet
  • Cirque Du Soleil – Luzia


We were so excited about today.  We were going to Harvard University.  We headed to the Charles transit stop just a couple blocks away from the Wyndham Hotel.  Harvard was only a few stops along this transit line.  We got off and were right in Harvard Square.  Seeing Harvard in person was breath taking.  Not only were we excited to explore the university due to some of our favourite movies – Good Will Hunting, With Honours and Legally Blonde – it was a place of history, prestige, and honour.  With it only being a short distance out of Boston – Harvard is a definite must see, not only for its history, but for the architecture and structure.  

Harvard University

Our last event of our trip was to embark to Salem Massachusetts to learn about the Salem Witch Trials in a ‘Haunted Walk’ adventure by Salem Ghost Tours.  From our hotel, we walked to North Station – right next to the TD Garden where the Boston Celtics play.  We took the commuter train out to Salem. Our transit passes did not cover this cost, but the train fair was very reasonable and we were able to purchase a family pass even though our children were older than what it was allowing.  

Stepping off the train into Salem was something out of a movie… a horror movie.  In all honesty – the place was eerie and silent.  There were other people around, but we felt like we were being watched.  It could have just been us, but we all felt it.  One thing to note is that there is only 1 public washroom around (at least during the time period we were there).  We had booked a nighttime haunted walk, so no shops or businesses were open.  Keep this in mind if you are going to visit the town.  The tour was very informative and interesting.  We learned a lot about the witch trials and the town itself.  We were unsure what the tour would be like, but our tour guide was very informative and it was an hour history lesson into the lives of some young women.  The town even has the house where the board game ‘Clue’ was based from.  We were told that if you stared up to the windows, you could see a ghost.  We are unsure if we saw one, but the experience was fun.  

Salem, Salem Witch Trials, Boston
Gravestone of one of the ‘Salem Witches’

Summary of Day 3:

  • Harvard
  • Salem – Salem Witch Trials

Day 4:

We left historic Boston on Day 4.  Our flight was another early one, so we were at the airport by 7am.  

Thoughts and Tid Bits…

Would I go back? YES!  Most definitely.

Would I stay in the same hotel?  Yes, the location was superb. It would be nice to have a new experience in a different hotel, but it would be hard to beat the Wyndham Boston Beacon Hill

What area’s would I explore more?  Beacon Hill, more of the Habourfront, see a Boston Celtics game, or Boston Bruins or a Patriots Game and go to the Aquarium. 

Boston is filled with fantastic food.  You don’t need to eat at expensive restaurants all the time.  Some of our best food was local diners – like a Mexican place across from the Wyndham.  We ate there twice – (Anna’s Taqueria)

Don’t be afraid to explore and be spontaneous.  I am a huge planner, but one of my favourite moments is falling upon the Puerto Rican fair.  The music, food and amusement rides were definitely a highlight.  


Buy a subway/transit pass to get around.  The system is super easy – colour coded as per area you want to go to.  It is inexpensive as well, especially for a family of four. To find out more, go to

For those of you travelling from the Ottawa area, drive to Syracuse for flights.  Cheaper airfare rates – we flew JetBlue and there is a hotel basically right at the airport that will keep your car (Staysure Plus Hotel by Best Western).  They do have a shuttle from the hotel to the airport, but we walked from the hotel to the airport in a short 8 minute walk. 

Stay in the Beacon Hill area if you prefer culture and history. Stay at the harbourfront area if you prefer being in the mix of activity.  You can conveniently book your hotel via or click the link to stay at the Wyndham Boston Beacon Hill like we did.

All in all, we LOVED Boston and would go back in a heartbeat.  You will laugh at the Arts and Culture at Quincy Market with its buskers.  You’ll cry at the history of the Freedom Trail and you will be in complete awe at the entire package Boston has to offer.  Pack all that up into your luggage and you will be destined to have a trip of a lifetime.  I promise you.  

Boston Harbour

For another iconic city review, visit my Summer in NYC blog.

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