it's all about me; boston

Boston: how I love thee

it's all about me; things to do in boston


Boston: commonly referred to as Bean Town, America’s Walking City and The City on a Hill. Now known as Sarah’s-favourite-freakin’-city-in-the-U-S-of-A.

Hubs and I travelled to Boston for the first time recently. Holy crapola! Every single thing about it was fantastic. I’m revelling just thinking about our trip again.

Boston is one of those cities I picture myself living in. Mind you I would be 38.4 pounds heavier from all of the deliciousness. It is a city rich with history; sprinkled with modernism. People are classy and everyone has great shoes. Seriously, that’s enough of a reason to move right there, no?

We were in Boston 4 nights, 5 days and I feel like we only scratched the surface of what the city has to offer. It was a quick flight from Billy Bishop to Logan. We considered driving but Porter Airlines had such a great seat sale it saved us money in the end … and our marriage. Plus flying back onto the island at night was pretty cool.

it's all about me; flying porter toronto

In case you haven’t already figured it out, I am officially in love with Boston. It’s true. Not sure if it’s possible to be in love with a city but I’m pretty sure it stole part of my heart. My head is all spinnie trying to figure out where to even start to declare my love for it. I’d write one big run on sentence so not to give something preference over another but quite frankly, I’d run out of breath and the grammar geeks would be all over me. Seriously, it was all that fantastic.

So, no better place to start than something truly magical. <deep breath>

Whale watching

When we started to plan our trip, whale watching was on our bucket list. Small, not-so-small, problem: I get severe motion sickness. As in barf after every flight motion sickness. Take Gravol to ski motion sickness. Look straight ahead while driving motion sickness.

One of my cousins is an ER nurse and she recommended Scopolamine, aka Gravol on steroids. It’s these little patches that go behind your ear and are available from your pharmacist. Well, winner winner, chicken dinner! Smooth sailing. Literally.

We cruised 25 miles out on the Atlantic to Stellwagen Bank Marine Sanctuary. It was a beautiful, calm morning and I was counting my blessings. When we arrived we were greeted almost immediately.

it's all about me; whale watching; boston harbor cruises; things to do in boston

While we were there 6 different humpback whales surfaced. These ginormous creatures would rise, blow and crest back down into the depths of the ocean. It was a magnificent sight.

Boston Harbor Cruises was so respectful of their presence. We did not chase the whales but rather let them come to us. It felt like a staged performance the way they would swim along side of the boat.

Hubs and I were both so in awe we considered booking another tour the next morning. That would have required us to make a decision and even on the best of days neither one of us are good at that. What we did decide – intentionally or not – was that we would save it for another trip.

Tip: while cruising we asked one of the naturalists the best time to go whale watching and they recommended an afternoon cruise. Apparently whales are more playful after lunch.


I have no idea how every single person in Boston isn’t overweight. The food was dee-li-shish. It was hard coming home to white bread and butter, the extent of my cooking abilities. Heh, I’m trying to learn, ok?

Our first meal was at Pastoral, an artisan pizza place. We split a fennel sausage and ricotta pizza and Caesar salad, which had pizza crust for croutons. Brilliant! The food and service were both fantastic and set my expectations high.

The thing is the rest of our meals were equally amazing. From food trucks to seafood places, nothing disappointed our taste buds. A few other must eats in Boston:

  • The Barking Crab is a casual shack full of life. It’s a funky harbour side restaurant with sinful hot crab dip and spiked bevies.
  • For sweets head to Flour Bakery & Cafe. They have brownies the size of your head.
  • Whatever you’re in the mood for, whether it’s casual or fine-dining, hit up Legal Seafood. According to hubs they have the “best fish and chips”.
  • The food trucks weren’t just your fries & pogo type stop. They were a gourmet feast. The Dining Car was well worth the wait.  I had a pulled pork sammie that melted in your mouth.

It's all about me; where to eat in boston; things to do in boston

Tip: eating at food trucks for lunch is a great way to keep meal costs down.

Boston Sites

We had zero itineraries and I wouldn’t change a thing. After getting caffeinated in the morning, we would walk out the front door of the hotel and walk. And walk and walk. By day two I gave up on the cutesy, outfit-coordinated sandals and opted for runners.

Walking aimlessly around Boston was a highlight in itself. The buildings are charming and streets a drivers worst nightmare. History surrounds every inch of the city. Truthfully I felt like a schmuck. I wish I would have gone in with a bit more knowledge of the background.

Unplanned we ended up seeing Boston by region: East, West, North, South as far as our feet or the Line took us. Finding the Freedom Trail is inevitable if you’re on foot. We ended up in the Commons one day, looked down and there it was. So we followed it.

The red line walks you to the main historical sites in Boston. Each landmark is well marked with descriptions of the significance of that spot.

It's all about me; what to do in boston; things to do in boston

Whether it’s your first, fifth or fiftieth time to Boston, you’ll want to make your way to:

  • Faneuil Hall Marketplace. It’s a playground for the bigs and littles. From shopping and eats to buskers and street theatre, it will keep the whole family entertained.
  • The USS Constitution. We walked from the South to the North end shipyard one day. Whether you’re a boat or navy person or not, it was fascinating being on a vessel built in 1797. They don’t build ‘em like they used to. And ladies, if you’re not interested in a boat, you will be interested in the uniformed men stationed about. Trust me.

I may have been a wee bit cranky after walking in the heat for 5 hours. And by wee bit I mean chewing hubs’ face off because he wasn’t willing to piggy-back me to the hotel. Just on the other side of the shipyard is a water taxi station. Thank gawd as at this point I was done walking. It was an inexpensive and fast way to get us closer to the hotel. Also a neat way to see the city from the other side.

  • Boston Public Gardens to slow down and re-energize. We had time to kill on our last day before heading back home. We made our way to the Gardens where we lay on the grass and people watched. All of the green spaces in Boston are beautifully manicured. The Garden is lined with different species of trees, all with small descriptors. I appreciated knowing what it was I was looking at.
  • Take part in the singing of Sweet Caroline at Fenway. Living with an obsessed sports fanatic, there was no way we were skipping Fenway. I planned our trip around the ball scheduled and picked a week the Blue Jays were in town. I know, wife of the year.

There is so much to this park. Hubs was like a little kid zigzagging from here to there taking it in. My tiara goes off to the Red Sox as they do an incredible job at engaging their fans. If you ever need a Director, Fan & Community Development, I know one. Call me.

it's all about me; fenway park; boston red sox; things to do in boston

Tips: ditch the style and go for comfort. Your feet will thank you. Take the Line. It’s an incredibly accessible city and public transportation will keep site seeing costs at a minimum.

Where to stay

I can’t deny it, I can be a bit of a frugal princess. I want the champagne and caviar on a beer and wings budget. The Westin Boston Waterfront met those criteria and more.

We’ve all said that we don’t want to feel like just a number; that we want a personalized experience. This is what the Westin Boston Waterfront provided us. Before we had even stepped foot in Boston, we knew we had made the right choice when Anna, their marketing manager, contacted us.

Check-in was seamless. The lobby was busy but the front desk was well staffed with friendly people. Because we arrived in Boston in the morning, our room wasn’t ready yet. Not a big deal as they stored our bags so we could start our adventure.

When we arrived back later that day and made it to our room it was clear they had been stalking us. Two washrooms. His and hers. Thank you sweet baby geezus.

The beds are the type you can never replicate as hard as you try. Oversized. Uber comfy. I swear I haven’t slept that well since.

The details are what I noticed the most. As soon as you walk into the hotel, there is a vertical garden. The green leaves of the garden are subtly placed throughout the entire hotel. The bars of soap in the washroom are a green leaf. Their attractions/features book has a green leaf theme through it. It’s the small things that I appreciate most.

Oh, and remember the Red Sox versus Blue Jays game? Their staff arranged those ah-maze-ing seats for us. Seriously. They can do anything.

it's all about me; westin boston waterfront

Tip: save your precious time and book at the Westin Boston Waterfront.

As I sip my caffeine out of my Boston Starbucks mug, I am dreaming about our return to Boston. What are some of your favourite things to do in Boston? Leave It’s All About Me your suggestions in the comments below.


*Header image source: Captain Leisure Tees. All others are ©MrsARob


2 Responses

  1. Sarah, thanks for sharing your trip to Boston with us! It is one of the cities I have always wanted to isit in the US. You have moved it up on my list that I have to see. I also loved your picss, and will keep in mind all of your suggestions for when I finally make the trip there!

Leave your babble below