Boston – Part 1: More Than A Feeling

Boston City Skyline from Boston Harbor


Why Boston? Everyone kept asking. Do I need a reason to travel somewhere? I’d reply. However, there was a purpose to the trip. Myself and two other bros were on our way to Fenway Park. A classic stadium and piece of Americana that is so dear to locals and baseball fans that the park has been open for the last 102 years. As it turns out, there is an inexpensive flight from just over the US border in Ogdensburg, NY. Cape Air, now has flights from there to Boston with connections in Albany, NY. It’s only an hour flight per hop and if you sit close to the front you have full view of landing in Boston, like the video posted at the bottom of this article.

The subway system in Boston, simply called “The T” is well laid out and easy to understand. For $17 you get an unlimited 7-day pass. This was a no brainer for us. It offered full access to the city for the price of a taxi ride.


We stayed at the FriendStreet Hostel. Luckily picked the smallest room. Only six beds and it had air conditioning. It was so hot for the first three days that after walking all day. To come in to a chill room with A/C was like striking gold. The common room was way too small however and usually crowded. Ironically, there is a large cafe on the bottom level next door that was usually empty. The staff was nice and accommodating however the cleaners don’t bother with a courteous knock on any doors before walking in. Food options in the cafe are lacking and management should consider switching the cafe and common room.

Cape Air flight from Ogdensurg, NY to Boston, MA

Day 1:

We arrived early enough that most Bostonians were doing their morning commute. We crowded the streets with them but while most are looking forward we’re looking up and around (tourist trait 101). The architecture in Boston has an excellent blend of old & new. Is that too cliché? How about old brick pubs with wooden facades and cobblestone streets interlock with glass and steal giants to show a city that is mature yet still growing. I still like the first sentence. And so we walked, making mental maps to interesting places for later.

Quincy Market Downtown Boston

The tourist epicenter seems to be Quincy Market. Nope, that’s not Boston Market. This is a covered market the panders to the fanny pack and Disney shirt wearing crowd. While the variety is good, it lacks any real authenticity as a market. I would have tried many things but my wallet was giving me the silent treatment once it saw the prices, inflated to say the least. A much better option is Haymarket. Available Friday and Saturday, this is where your wallet turns its frown upside down. Get your meal on here. There’s a large quantity of fruit and vegetables for a dollar. I got a slice of pizza for a $1.50 ($4 a slice in Quincy Market) Prepare to be mocked “spoken to” by the vendors however this comes across as folksy Boston banter rather than a confusing concept of customer service. It’s easy to find, there’s a subway stop for Haymarket.

Right across from Quincy Market is Faneuil Hall. In the early years of the city, Boston lacked a place for government to meet. Mr. Faneuil had the hall built and it is now part of the National Park Service. It is also air conditioned. So we cooled off while getting a history lesson on how the hall came to be. It’s worth a stop just ignore the gift shop on the first floor. My nose and stomach agreed on a smell across the street so we had our first lunch at Salty Dog Seafood Grill & Bar. This is where I had my first oyster… and raw clam. I then had several more and I’m getting hungry again just writing this.

Trying Oysters in Boston

Looks good eh? Next stop was Cheers. Where no one cares about your name and you’ll have to wait for a seat. The lower bar, down the classic steps, is tight quarters and takes the longest to get a seat. They’ve expanded on to the floor above which is a bit easier to eventually get a seat. Turn over isn’t bad at the bar as people usually just have one drink, say I’ve done it, and continue on with their tour. That’s all we did as well. It was cool to see a beer in that cheers beer mug yet it’s really nothing that special unless you’re a fan of the show.

Cheers bar Boston, MAbeer at cheers, Boston MA

After the beer at cheers we decided to go for a drink. There is a roof top restaurant called Top of the Hub on Boylston St. Prices are on the high side and after looking at the bar, we were underdressed in shorts and t-shirts so we got flagrantly seated towards the back end of the restaurant were we noticed other similarly dressed people. Yet we made up for it by sipping away at their finest, cheapest, scotch. It has great views of the city, I snapped just a few pictures of the skyline then we bounced. After almost 18 hours since opening my eyes I was beat and there was still so much of Boston to see and do.

Boston from a roof top bar
Boston from a roof top bar

Day 2:

Started slow as we woke up late and went for breakfast. It was already a balmy temperature so with humidity setting in during the morning commute we made haste for the even more humid subway to follow the freedom trail and check out bunker hill monument and warships USS Constitution and USS Cassin Young.

Bunker Hill Monument, Boston

The freedom trail, which the website says is only 2.5 miles feels much longer, I mean, check out this map. Make sure you have walking shoes as it will take you to 16 historical sites around the city. We broke it up a bit and decided on the Bunker Hill Monument. On June 17, 1775, this was the first battle of the American revolution. The pleasant neighborhood around the hill makes the uphill walk more enjoyable. Red white and blue decorate many of the homes the closer you get to the monument. After walking uphill you’re rewarded with another 192 steps to reach the top and look out on to Boston. Since the Sun was blazing that day, they shutdown the entry because people can pass out from the heat. Sad to be missing the view but the Sun was already starting to seep in to my Irish skin. The freedom trail took us down the hill, zigzagging through parks to the Charlestown Navy yard.

USS Constitution Boston

USS Constitution Boston

Here sits the USS Constitution. An American revolutionary warship who’s nickname is “Old Ironsides” since British cannons were seen bouncing off the hull during battle. Worth a look around, there must have been 20 cannons per side. Serious firepower for the day! If you want to know more check out the museum. Also docked in the Naval yard is the USS Cassin Young. A World War 2 destroyer who saw action in the pacific most notably at the battle of Okinawa. This was a real treat for me. A well preserved piece of WW2 history from the pacific war with Japan. An often overlooked part of WW2 with most attention going towards Europe.

USS Cassin Young docked at the Boston Naval Yard

Guns of the USS Cassin Young Boston

Everyone was over heating at this point so it was obviously time for more oysters. So off to cool down in the room for a bit before going back to the market area in search of the delicious little buggers. Mission accomplished. Also on the menu was vodka shots with oysters and cocktail sauce. It was too good, just look!

Boston Oysters

Boston Oysters shots with Vodka

Stay tuned for day three and four and the highlight of the trip, Fenway Park. Oh yeah, almost forgot. Here’s landing in Boston:

6 Responses to Boston – Part 1: More Than A Feeling

  1. The city is certainly on my bucket list for its amazing architecture and history. Your menu choices are definitely far from what mine would have been, looking forward to day three and four.

    Taryn Chambers September 14, 2014 at 11:29 pm Reply
    • Thanks Kiddo! You would enjoy it, it’s right up there with New York for architecture. New Mission: Get you to eat Oysters.

      Shaun September 15, 2014 at 1:16 pm Reply
  2. I think your next American stop has to be Chicago. Just a beautiful city and cool sights, I will be heading there again next year maybe for their Blues Festival

    Ron September 17, 2014 at 6:25 pm Reply
    • I’d like to go there as well and see Wrigley field and have some deep dish pizza!

      Shaun September 18, 2014 at 1:15 pm Reply
  3. How lucky I stumble upon your blog today! I am actually headed up to Boston tomorrow morning for the weekend. It’s my first time there and I’ve got absolutely nothing on the agenda. I will have to take a look at your recommendations and keep them in mind! I happen to be a huge fan of oysters.

    Amanda | Chasing My Sunshine August 14, 2015 at 9:17 am Reply
    • Then you’ll love it! I recommend the vodka, tabasco sauce and oyster shot! Most places should have it. Hope you have a great time!!

      Shaun August 14, 2015 at 9:53 am Reply

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