Travel Diary: Boston

boston college2

This is Part II of my New York/Boston trip that my husband D and I took a few weeks ago.  If you’d like to read my travel diary on New York, please click here.  This one will focus on the few days we spent in Boston.

We flew from Boston from New York via Jet Blue.  I was so impressed by this airline – they’re what WestJet used to be before they got too big and full of themselves.  The customer service was great, they had free tv on the plane and you weren’t squished like a sardine sitting in economy.  Unfortunately they don’t fly out of Canada but I’d definitely fly with them again if I have a chance.

Where we stayed:

Sheraton Boston

Unfortunately I completely forgot to take pictures of our hotel room, aside from the view we had:


The view from our room at the Sheraton Boston

No complaints there!  We were lucky enough to be upgraded to a suite.  Our room was really nice, it appeared to be recently renovated.  We had a separate living space and then a bedroom and full bathroom.

The hotel itself was really nice as well; it was connected to The Prudential Center Mall via a covered walkway, which I’m sure would be beneficial during the colder months.  We were within walking distance to all the big attractions including Fenway Park, Boston Common, Newbury Street, etc..

What we did:

Red Sox Game @ Fenway Park


View of the field at Fenway Park

Okay I am really not a fan of baseball (at all) but D really wanted to go to a game so we went.  And I’m still not a fan of baseball.  But the history of the park is pretty cool – it was built in 1912 and is the oldest ballpark in major league baseball.  It’s obviously been renovated and restored many times since then but it’s still cool to walk through it knowing just how old it is and how much history exists amongst it.


Fenway Frank and Cracker Jacks!

The highlight for me at any sports event is generally the food and this one didn’t disappoint.  You have to have a ‘Fenway Frank” when you’re there and I did and it was the best hot dog I’ve ever had.  Had to throw a bag of Cracker Jacks in just because – although I remember them tasting way better when I was a kid.  There were many other things I would have liked to try but we were going for dinner after the game so we didn’t want to spoil our supper.  (Hindsight, the hot dog was much better than what we had for dinner that night, should have just eaten at the game)

Boston Duck Tour


Boston Duck Tours

This was something else that D wanted to do – I was skeptical about the whole thing.  I had seen these in other cities and they just seemed so touristy and cheesy.  Honestly it was both but also entertaining and informative and I’m really glad we did this.  Basically you tour the city in a World War II amphibious vehicle – meaning it can travel on land and water.  Our tour operator was hilarious and made the tour for us.  In between his dry jokes he gave us a wealth of info about Boston, it’s neighbourhoods and its history.  You also get a good feel of the city in terms of where things are and what attractions/sights you’d like to visit so I’d recommend doing this early on in your trip.  Tickets are about $35/person so for the 80 minute tour, we found it to be good value.  Plus this gives you a free pass to quack at passerbys on the street without them thinking you’re odd (they encourage this).

Freedom Trail


Sam Adam’s gravesite

This is a red trail that winds its way through various neighbourhoods in Boston and showcases various historical sites.  I’m not big on history but there were definitely some cool things to see here – Sam Adam’s gravesite, Boston Common, Massachuchets State House, etc.  This is a long trek (2.5 miles long) and we did it on a hot day so comfortable shoes and water were important.


Boston Public Garden

We didn’t do a guided tour, instead we picked up a brochure and map and did the tour ourselves.  The map cost $2.50 but it looks like you can download the brochure online for free or they have a smartphone app for double the price.

Quincy Market/Faneuil Marketplace


Outside of Quincy Market

Quincy Market/Faneuil Marketplace is a combination of shops, restaurants, and a 40 vendor food court.  We were so irritated with ourselves because we searched and searched forever trying to find a place for lunch and we ended up at Bostonia Public House, which was disappointing.  After lunch we realized Quincy Market was just down the street and the food court there is insane.  There are so many options including fresh clam chowder, lobster rolls, pizza, sandwiches, bagels, indian, pasta…the list goes on and on and everything looked and smelled amazing.  Lots of cool little shops around here too.

Where we ate:

Five Napkin Burger

We snuck in here for lunch shortly after we arrived as it was close to our hotel.  It was okay, nothing special.  I found my burger dry and kind of bland.  I had this on my list to try in New York and maybe it would have been better there but I don’t think I’d go back.

Regina Pizzeria (Fenway)

I had read that this was some of, if not the best, pizza in Boston.  It’s been around since 1926 so I figured based on that fact alone, how could we go wrong.  Well, we got ready for dinner and I misread their website and thought this was a full-service restaurant, when in fact it was actually a take-out restaurants with a few tables inside to sit at (fast-food style).  So that was a bit of a let down but we figured we were already there, we might as well just try it out.  We go inside and the only slices they have left are cheese, which is not usually our preference.  New pizzas wouldn’t be ready for 15 minutes or so and we were hungry and impatient and didn’t feel like waiting.  So we order 2 cheese slices from the very surly and cranky guy behind the counter (who I’m assuming was the Manager – he was barking orders at everyone around him) and  left.  Seriously, this guy was such a jerk to us, other customers, and his staff;  it was some of the worst service I’ve had in a restaurant in my life.  Fortunately (or unfortunately?) the pizza was delicious.  Very thin crust that wasn’t soggy (rare but very important!) with a ton of flavour which was surprising given it was only cheese.  I guess that’s how he stays in business!  There’s quite a few other Regina’s locations around Boston so I’d definitely go back but not to the Fenway location.

Bostonia Public House 


Clam Chowder @ Bostonia Public House

We stopped here for lunch after wandering around and getting lost in what I think was the Financial District for what felt like hours, looking for a place to eat.  We shared a bowl of Clam Chowder and I had a Lobster Mac n Cheese and D had a lobster roll.  The Clam Chowder was really good but the mac n cheese and lobster roll were just okay.


Lobster Roll @ Bostonia Public House

The disappointing thing here was the service – we waited a good 10 minutes to be seated because the hostess was no where to be found.  We were the only ones waiting for a table so it’s not like there was a long line of people.  We literally had 4 different servers walk past us (some more than once) and tell us that “Someone would be with us in a minute”.  Finally someone who I assume was the Manager came by and seated us (literally right next to where we were waiting), which was good for them because we were just about to turn around and walk out.  I understand that a hostess has their role but if the hostess is no where to be found and you see customers waiting to get a table, is it that hard to direct them to an empty table and hand over some menus?  Anyway, the icing on the cake was that our meal was just okay so definitely wouldn’t return.

Stephanie’s on Newbury


Breakfast skillet @ Stephanies

We went here for Sunday Brunch and it was sooo good!  They had a Bloody Mary Bar that I took advantage of and it was awesome – you could pick your vodka, mix, and garnish – to which I added a dill pickle, and a pepperoni and cheese spear.  I’m much more of a sweet drink type of person so this was actually the first time I’ve ever tried a Bloody Mary (I know) and it set the bar pretty high.  I’m not sure I’d drink these all the time but they were a nice change from the sugary drinks I usually have.


Eggs benny @ Stephanies

Anyway, the breakfast here was also really good.  I had eggs benedict and D had a breakfast skillet which was HUGE and included bacon, sausage, home fries, eggs and cheese baked in this large cast iron skillet.  Both were really yummy and large portion sizes.  Our service was great too so I’d definitely recommend this place and we’d go back.  I’d love to give it a try for dinner.


We decided to save a dinner in Boston’s North End for our last night.  The North End is famous for its large number of Italian restaurants (100!) and is similar to New York’s Little Italy, although much smaller!  I feel like I spent hours scouring Open Table looking for the best restaurant to make reservations at, although everyones opinion was that every restaurant here was good.  I ended up choosing Beneventos and we took a cab there, given that our hotel was a good 45 minute walk to the North End.  We checked in and proceeded to wait a half hour past our reservation time to get our table.  We weren’t concerned as we had no where to go but its something to keep in mind as I suspect that this is the case with most of the restaurants in this area.  While we were waiting, people were coming up and asking the host how long the wait was and most times the answer was at least an hour and a half.  Yikes!  Really glad we made reservations at this point.

We finally get our table which was tiny – but that was the theme with the whole restaurant, it was packed to the brim and you’re practically rubbing elbows with the people next to you. After reviewing the extensive menu, my eyes became bigger than my stomach and I ordered a vodka pizza (vodka sauce, mozzarella, proscuitto, and basil) to start and baked gnocchi in a tomato cream sauce.  D ordered an appetizer of lobster ravioli and chicken marsala as his main.  I discovered very quickly that this was way too much for for us and we couldn’t even come close to eating them all.  Such is life!  All 4 dishes were really good though!  Was it the best Italian I’ve ever had?  Probably not but it was a good meal.  And our server (whose name escapes me) was fantastic – she had so many tables I don’t know how she could keep anything straight but she was on top of everything and so friendly.  So would we go back here?  Probably not, but not because it wasn’t good.  Because there are so many other options in the North End that I’d like to try.

Mike’s Pastry


So you’d think that after that monstrous meal we had at Benevento’s that would have been enough for both of us but I had heard that Mike’s Pastry shop had the most amazing pastries and cannolis and I knew I had to try something from there before we left Boston.  So we made our way to the shop and discovered that the line to get in was halfway down the street and wrapped around the corner.  Much to D’s dismay, I took a place in line.  We waited for 45 minutes and by the time I got to the front I was so overwhelmed by the choices they had.  We ended up with two types of cannolis (Strawberry & Oreo) and a slice of Boston Cream Pie (when in Boston…).  They wrap up your choices in a box and tie it with string and send you on your way.


From left to right: Boston Cream Pie; Oreo Cannoli; Strawberry Cannoli

We took a cab back to the hotel but I wish we would have walked because then maybe I could have found some space in my stomach to eat these.  The crappy picture above does not do these justice – the cannoli’s were HUGE, like probably 3 times the size of a normal cannoli and just stuffed to the brim with pastry cream.  I managed to take a couple small bites of each of them (both were seriously amazing) and a bite of the Boston Cream Pie (wasn’t impressed – super sweet and gritty?) before I fell into a sugar and carb induced food coma.  We stuck the remnants in the fridge, hoping to devour them the next morning but our flight was really early and we were both still so full when we woke up so they ended up going to waste.  Which I’m still seriously sad about.  But I’d go back here and stand in line for 45 minutes again for those cannoli’s in a second. Yum!

And that was Boston!  We enjoyed the city and were amazed at how clean it was (especially after being in New York, although that’s not really a fair comparison). We were there for 3 full days and felt that was more than sufficient for us to do the things we wanted to do.  If I were to ever visit again I think I’d like to stay in a hotel closer to the waterfront/Quincy Market as there seemed to be more options for restaurants and plenty of shopping/attractions nearby as well.

If you have any questions about our trip please let me know.  As always, thanks for reading!



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