My Trip to Boston

If you haven’t read my post on Part 1 of my trip, be sure to check that out first.

Day 5: Wednesday, June 6

In the morning I headed to the bus terminal in New York City with my luggage. When planning my trip, I looked at flying from New York City to Boston versus taking the train or bus. I decided to take the bus since it was by far the cheapest option and wouldn’t take much longer than flying. If I flew it would take me about 3.5 hours (this includes time to get to and from the airports in both cities and through security), while the bus would take me 4 hours. I ended up buying a bus ticket with Megabus for only $10. (I wish I could get a bus ticket between Toronto and Ottawa that cheap, but I digress.)

There’s not much to say about my first day in Boston. I arrived in the evening, explored the downtown and got something to eat. I was mesmerized by how much history I was surrounded by. I went for a walk in Boston Common. Found in 1634, it’s the oldest public park in America. This is only of taste of the history I’d be in store for on my trip to Beantown.

Similar to New York, I bought a 7-Day Transit Pass for $21.25. Boston has an excellent subway system. It’s modern, affordable and clean. Many people think New York has the oldest subway system in America. Wrong. It’s actually Boston. Although Boston doesn’t have as many subway stations as New York, I felt safer riding the subway in Boston.

The Airbnb where I was staying was in a super convenient location, a 20 minute subway ride from downtown Boston. I’m happy to say it was located in a nicer neighbourhood than my place in New York. I had a long day of travel, so I decided to check in early and get a good night’s rest for a full day the next day.

Day 6: Thursday, June 7

On my first full day in Boston, I took the subway to downtown Boston. One of the main reasons I went to Boston was the “Big Dig.” In case you’re unaware, the Big Dig is a major project where Boston transformed and revitalized its downtown by burying its once elevated freeway. Although the project went way over budget and years over schedule, it was considered a success by many. I was curious to see how Toronto could look one day if the politicians here decide to bury the Gardiner Expressway.

The Big Dig lived up to its name. Downtown Boston was free of freeways. In place of where the freeway used to stand was the Rose Fitzgerald Kennedy Greenway. This is a lovely place to relax, walk or sit outside and enjoy on a nice day.

Boston isn’t as big as New York City, so I bought tickets for a 1-day hop on hop off bus tour with Boston Old Town Trolley Tours. Included with the bus pass with a visit to the Boston Tea Party Ships & Museum. I didn’t know Boston very well, so I took the full bus tour around the first time without getting off at any of the stops.

Once I felt like I knew Boston a little better, I got off my first stop at the U.S.S. Constitution Museum, a museum that aims to spark excitement about maritime heritage, naval service, and the American experience. The museum was interesting, but even more fascinating was the U.S.S. Constitution herself. Launched in Boston in 1797, she’s the oldest commissioned warship afloat. She earned the nickname "Old Ironsides" during the War of 1812 when she fought the British frigate.

After I headed to the Bunker Hill Monument. This monument was built to commemorate the Battle of Bunker Hill, which was among the first major battles between British and Patriot forces in the American Revolutionary War. It’s pretty easy to get there from the U.S.S. Constitution. Just follow the red brick road. When you’re at the Bunker Hill Monument, head across the street to pick up FREE tickets to climb the inside of the monument. It’s 294 steps to the top. (This was a piece of cake since I’ve climbed the stairs to the top of the CN Tower.) It’s well worth the journey to the top. You’re given a marvelous view of Boston.

Once I got back to the bus stop, I headed to the Cheers bar. No trip to Boston would be complete without a stopover there. Fun fact: there are actually 2 Cheers bars in Boston. If you’re looking for the one that inspired the TV show, head to the one at 84 Beacon Street. Visiting the Cheers bar was a lot of fun. I took a photo outside before heading inside. There’s a gift shop and a set bar where you can drink a pint or go for dinner.

I finished the evening off by heading to Fenway Park to see the Boston Red Sox play. The Red Sox ended up losing 7-2 to the Detroit Tigers, but I still had a good time. Being at Fenway Park was a treat on its own (more on that later). I bought cheap seats, but still had a great view of the action. (Although one obnoxious Boston Red Sox fan kept insisting I was in the wrong seat and found me a “better” seat. The seat was closer to the action, but right in front of the aisles, so my view kept getting obstructed, so I left at the bottom of the 8th inning.)

Day 7: Friday, June 8

I started the day by heading to the Boston Tea Party Ships & Museum. This is a great way to learn about the history of Boston and the Boston Tea Party itself, where the Patriots fought against the British for imposing “taxation without representation.” The staff were wonderful at the museum and were in character the entire time. You even get the chance to throw tea off a ship!

In the afternoon I headed to the New England Aquarium. I’ve a big fan of aquariums. I’ve been to the ones in Vancouver and San Francisco. The penguins at the New England Aquarium are so cute!

Next, I headed to Boston’s Dreamland Wax Museum. The wax figures there were quite lifelike, especially the Snoop Dogg one. The best part of the museum is the U.S. presidents wax figures. The museum has wax figures of all43 presidents. (I’m surprised no one has defaced the one of Donald Trump.)

Boston is a city known for its world renowned colleges and universities, so I headed to Harvard and MIT. Although I didn’t go inside the buildings, it was neat just to be walking around the campuses that so many bright minds come from.

Day 8: Saturday, June 9

My last full day in Boston started in a strange way. I was walking to the subway station to go on a tour of Fenway Park. I was almost there when I saw the subway coming, so I started to jog to make it. I noticed that the sidewalks looked new, but there weren’t any barriers up, so I figured it was dry… NOPE! I walked right into the wet cement with my running shoes, getting covered in cement. Luckily a neighbour was nice enough to come out of her house and give me water and paper towels to clean myself up. She said that it was her mother's funeral that day. Her mom was always helping strangers out, so it was fitting that she was helping me out today of all days. I thanked her for her kindness and encouraged her to be happy since her mom would want her to be in good spirits. The funeral was a celebration of her mom's life. At least she had a funny story to tell at the funeral. Hopefully I made her feel a little better on a difficult day. I appreciate her kindness though.

Once I got cleaned up, I headed to Fenway Park for a tour of the baseball stadium. Fenway Park is Major League Baseball’s oldest baseball park. The Boston Red Sox have been playing there since way back in 1912. It puts the Rogers Centre where the Blue Jays play in Toronto to shame. The tour was a lot of fun. The tour guide was great and had a lot of interesting stories to share. For example, Fenway Park’s blue grandstand seats are the only remaining wooden seats in baseball. I went on top of the Green Monster (or as Bostonians know it, the “Green Monstah.”) Fun fact: It was built because too many players were hitting homeruns out of the baseball stadium, damaging cars and buildings. There’s even a rooftop farm on Fenway Park that provides fresh produce to Red Sox Nation.

In the afternoon I went to the Old State House. Similar to the U.S.S. Constitution Museum, it’s a great way to learn about the history of Boston. I finished off my time in Boston by walking along Boston’s poshest street, Newbury Street. It reminded me a lot of Yorkville in Toronto. I kept my wallet close to me and went “window shopping” instead.

Final Thoughts

I thoroughly enjoyed my time in New York City and Boston. If you’re heading to New York, I’d highly recommend that you visit Boston, too. Whether you’re into the outdoors, history or the arts, there’s something for everyone. Although I got to see most of what Boston has to offer, there’s so much of New York I didn’t get to see. I’m sure I’ll be back to the Big Apple sooner rather than later.

Sean Cooper is the bestselling author of the book, Burn Your Mortgage: The Simple, Powerful Path to Financial Freedom for Canadians, available now on Amazon and at Chapters, Indigo and major bookstores, and as an Audiobook on Amazon, Audible and iTunes.