Welcome to Boston……well……we have to get there first. The boss (Ms. Sheila) and I were discussing various options of get-aways recently and she reminded me we have not been anywhere together for a number of years! Who would have known?

With a limited amount of time available we ruled out a beach holiday. I guess we could have taken a short flight somewhere but ideally I wanted to drive and we were only thinking 4-5 days maximum. My restriction was that I wanted to be able to get there in no longer than 9-10 hours (so, basically one day of driving there and one day back). Another consideration was what we were going to do with Ms. Ellie - the 6.5 lbs. of fluff. We solved that by having Ms. Sarah take her back to London with her for her school week. I must admit, I had my missgivings about that.

In regards to places to go, I suggested NYC but Ms. Sheila wasn’t keen on going there and I had already been there twice this past year. So - I said “what about Boston”. I had been there maybe 40 years ago, so basically that means I have not been there and Ms. Sheila had never been there.

According to Google Maps the driving time was just under 10 hours so it checked the box of getting there is one day! I began the search for hotels and oh, my - what is going on with pricing?

I used to do a lot of traveling in my previous business life and for whatever reason the number $200 USD for hotels sticks in my head. I now know that’s not very realistic. We used to stay out by the airport in Chicago and we would always look for deals for under that price. I know I have not done a lot of traveling recently ……but come on?

I looked at various sites like Air Canada along with my Marriott membership. First choice was to stay downtown Boston, but that was going to be well over $700 a night. I knew the CFO (Ms. Sheila) was not going to go for that. For kicks, I also looked at NYC and the prices were very similar. If the NYC pricing had been lower then Boston, I may have been able to make a pitch for the Big Apple. I held off for a week or so, but eventually we had to pull the plug - I landed on the Courtyard South Boston. My research indicated it was close to the the transit (subway) and that was critical. I didn’t want to have to use the car in Boston and after walking around for two days, that was confirmed. A crazy place to drive.

We left quite early on a Tuesday morning and the drive to Buffalo didn’t take too long and crossing the border was very quick. Turned on the GPS and it indicated we would be there in around 9 plus hours.

We hadn’t eaten breakfast so after an hour or so on the New York Thruway, it was time to find something. Once you leave Buffalo a lot of the places that you would think you could turn off and go to are under construction, so a quick drop into a McDonalds isn’t an options. I saw a sign for a Denny’s and off we went. It turned out to not be the best choice as someone has a sensitive stomach (not me). It’s not the type of place for takeout so in we went, find some seats and got a much needed coffee. We both ended up ordering the Grand Slam Breakfast. I knew that this was not a low calories start to the day.

The rest of the journey went off without any crazy problems. A few stops for gas etc, and we got to Boston during the evening rush hour. Now it was time for gripping super tight on the steering wheel. The GPS did it’s best to keep up but it was definitely challenging with fast drivers on the highway and it didn’t help matters having no idea where I was going?

How did we ever do it before we had this portable GPS devices? The assistant navigator has a tendency to tell me to turn a bit late rather than suggesting to me that in 400 metres you will have to turn right. Our portable GPS isn’t very visible - meaning I had to look down and that’s not a very good idea when your driving - thus the assistant navigator needs to play an important role. Let’s just say there was a bit of tension in the car.

We arrived at the hotel, did the check-in and out the door we went. I knew that the subway stop was close but I wasn’t quite sure how to get there? Our hotel was overlooking at large plaza that hosted a few chain stores like Target, Best Buy and Panera Bread. With a bit of due diligence we managed to locate it. The hotel was in a bit of a sketchy part of town and so it was best to move along and not spend too much time looking around the area. We asked for directions from the front desk on how to get the MTA and we managed to figure it out on our own. It wasn’t very far - maybe a 10 minute walk.

I had a plan which I had not shared with the CFO (Sheila). I have recently become a “YouTube watcher ” of a crazy guy named Dave Portnoy who has become an Internet Celebrity through the creation of a website called Bar Stool Sports. He has quite a following (the kid - aka Ms. Sarah, even knew who he was) and he has an extremely popular series of YouTube video’s known as One Bite. He takes his passion for pizza and translates to the screen by visiting various pizza joints primarily in the North East of the USA. More about him coming in another blog - but he has ranked some places in Boston quite high and so I thought I would try to find one or two of them. Near the top of his list is one of the original pizza establishments in Boston called Regina Pizzeria.

The plan was to try to get there before it closed at 9 pm. It was going to be our first time on the transit system and it didn’t take us too long to figure it out. We purchased a 7 day unlimited pass and it worked out perfectly. The stop near us (Andrew) was only four stops to downtown and with a bit of help from Google Maps and a short walk we were able to find the restaurant. Its located in a section of Boston known as the North End and it has quite a history -

The North End, Boston’s Little Italy, is a maze of narrow streets with some of the city’s oldest buildings. On the self-guided Freedom Trail, tourists pass historic sites like the 1680 Paul Revere House and the Old North Church, which played a key role at the beginning of the Revolutionary War. Italian restaurants, coffeehouses, pastry shops and old-school delis pack the area, especially on lively Hanover Street

We made it with lot’s of time to spare and we were able to get a booth right away. Definitely, very old school with a few characters sitting at the bar, tables of what looked like college kids and us - the tourists. We ordered a large pizza and a glass of red (wine). The place was quite full especially for a Tuesday night. I looked over at the bar and I thought I saw Paulie Gualtieri from the Soprano's? Maybe my eyes were deceiving me :)

The One Bite app has given this restaurant one of its highest scores so I was eager to see how it compared to our Toronto places. Tried my best - take the first bite - you know the rules. The flop was impressive and the taste is very NY style. It was good but not as good as I expected. Portnoy (One Bite) had scored it a 9.1. My rating would be around 8.5 - of course in my humble opinion. Maybe the expectation was simply too high!

After dinner we headed back on the train to the hotel and called it a night. It had been a long day with all of the driving and having to get up early in the morning - time to hit the pillow.

We began the next day with a quick breakfast at Panera. The hotel didn’t offer a free breakfast and Panera was very close by and not that expensive. Time to venture into downtown Boston. First on the agenda was to do a tour of the The Freedom Trail. The actual trail is one that you can easily do on your own because the streets are clearly marked, however we had decided to take a guided tour beginning at Boston Common.

If I was doing it again, I wouldn’t take the guided tour. We bought a map/guide book and there are 16 stops listed on the Freedom Trail, however the guided tour takes you past only about 10 of them. I would have liked to have done a bit more walking but for some people the tour might make more sense. At each stop the guide provided us with a wealth of information about the Revolutionary War and the role Boston played between the British and the Americans. We ended up the tour near Faneuil Hall. By this time we were a little bit hungry so we re-traced our steps and went to a very non-Boston establishment called Shake Shack.

With the afternoon open we grabbed a train and headed towards Harvard. There was a tour starting at 2 pm and we signed up when we got there. We waited….and we waited but unfortunately we were told that the tour guide (who is a student) was not going to make it due to mid-term exams. But, the good news is another guide would be there for a 3 pm tour and we were welcome to take that one. I would say that the Harvard Tour for me was the highlight of the trip. The college is located in a very fashionable area called Cambridge and it has a number of interesting old buildings nestled amongst a number of shops, bookstores and cafe’s. You are surrounded by students and I’m sure my IQ went up 10 points that afternoon. The guide told us that the cost of attending Harvard College is $80,000 USD per year and that includes tution and room & board. If your parents make less than $100K a year will likely be getting full financial support - wow. The first year students live within the Harvard Yard and this is where the tour began.

The tour lasted about 90 minutes and although you can’t go into the buildings the guide gave us a very informative and fun tour of what it’s like to be a student at Harvard College. I gave it a 5/5. Following the tour we spent a bit of time exploring the shops around Harvard Square. There is a very interesting looking cafe/bakery called Tante. They have multiple locations in Boston and it was very busy.

We did a lot of walking today - 16.28 km and 22,483 steps to be exact. It was time to go back to the hotel and take a load off our feet. We were a bit indecisive on where to go for dinner. There isn’t a lot of options in South Boston near the hotel and so going back into the city is the best choice. I’m afraid to say we picked a place that isn’t your typical East Coast establishment - PF Changs. Alright….I get it. We’re not seafood people so lobster this and clam chowder that isn’t going to cut it for us. And, we do like PF Changs and they don’t have one in Toronto. We used to visit them when we had our condo in the Tampa area. It took us a bit of time to actually find the restaurant as I am pretty sure we around and around in circles more than a few times.

We began our second full day the same as we did the first with breakfast at Panera. Nothing super fancy - just a bagel and a coffee. The plan (if there really was one) was to try to find a street called Acorn Street in the Beacon Hill neighbourhood. I had read that it was one of the most photographed locations in all of Boston. We headed out on the train to the Charles/Massachusetts General Hospital train station and from there it was a short walk.

According to Google it’s ….One of Boston’s most picturesque areas, tony Beacon Hill has steep streets lined with Federal-style and Victorian brick row houses lit by antique lanterns. The gold-domed Massachusetts State House overlooks Boston Common, with its winter skating pond. Across Charles Street, home to chic boutiques and antiques shops, is the formal Public Garden. The Charles River Esplanade’s Hatch Shell hosts summer concerts.

I typed in Acorn Street into my maps and again, I just went around and around in circles. For whatever reason, I couldn’t figure out N/S/E/West…..I would turn one way whenI should have turned the other way. I knew it was close! Eventually we found it and wouldn’t you know it - there was a truck on the street.

One of the most photographed streets in the city, Acorn Street offers visitors a reminiscent ride back to colonial Boston. It was on this lovely street that 19th century artisans and trades people lived and today the row houses are considered to be a prestigious address in Beacon Hill. It is definitely an interesting area with lots of vintage homes and expensive shops on the main shopping area. After this we walked along Boylson Street and we managed to walk by a famous bar called “Cheers.” The boss didn’t have any interest in popping in but I had to see what is was all about…..

It was still fairly early in the day so I didn’t think it would be very busy - wrong I was. I walked down the steps and it was packed inside. The boss was wandering down the street so I had to hurry to catch her. Next stop on the journey was Newbury Street.

East of Massachusetts Avenue, Newbury Street is a mile-long street lined with historic 19th-century brownstones that contain hundreds of shops and restaurants, making it a popular destination for tourists and locals. Most of the "high-end boutiques" are located near the Boston Public Garden end of Newbury Street.

The street features all types of shops from the very, very high end (think Prada) to less expensive clothing establishments (Uniqlo) - scattered with lots of coffee shops and sit down eateries. A mix of Bloor Street (Toronto), Michigan Avenue (Chicago) and 5th Avenue/Soho in NYC. It’s quite long and by the time we got to the end it was time to circle back and think about going back to the hotel. Another 22,000 plus step day! This was going to be our last night in Boston so I had made plans to go back to the North End Boston and check out the different types of Italian restaurants available.

It felt like we were going back in time as we wandering down the various streets. The building were very old and I’m sure they looked the same as they did 100 years ago - short of the new retail places that were there. It was raining slightly and already dark. I had made a reservation at place called La Famiglia Georgio’s Restorante and as usual we had to use our GPS on the phone to find it.

We were given our table immediately and we headed upstairs to a large room. After we demolished the bread we ordered our mains - lasagna for Sheila and pasta for me. Oh..oh….unfortunately, the lasagna wasn’t going to work for someone. The filling was all cheese (no meat) and that was simply too much dairy for the boss. Only one thing to do - we had to switch plates. It was okay but I sure wanted the pasta! Had to take one for the team I guess. After this huge meal next on the plan was to go look for the most famous cannoli’s in Boston. We didn’t have to go to far and we bumped into more great looking restaurants and the world famous Mike’s Pastry. According to cannoli experts there are two places to try - Mikes and Modern. From what I’ve learned the tourists usually go to Mikes. I asked the boss if she wanted anything and she was emphatic in saying no….that would come back to haunt me later.

Very busy….I picked out 3 cannoli with chocolate chips. I would love to tell you how they tasted however after carrying them in the rain and home to Toronto, I never got the chance? And why would that be you might ask? After being home for a day or two, I thought I would go to the fridge and have one of these famous pastries…..checked each shelf and couldn’t find them? Looked further and found the box below on the counter?? WTF? Did Miss Ellie eat them or was it a much larger mouse? Anyways, I heard they were very good. Clearly we have a cannoli thief in our house and it’s not me or the dog.

So….that was enough food for a week. We were up very early the next morning to make the long drive home. Getting out of Boston was bit hairy but once we were on the highway it was smooth sailing from there. The dog (Miss Ellie) was staying with Sarah for the week and so we decided to head directly to London and pick her up rather than going home and then have to make another drive to London a few days later. We had enough driving…..

Our last shopping stop was Trader Joe’s in Niagara Falls. I’ve succumbed to them……stocked up on few favorites and then we headed across the border. Smooth sailing across and off to London we went.

Well that wraps it up for now. We had good time and it was very worthwhile. Still a few places we didn’t get to that are on list but that gives us a reason for another trip. See yah…

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