Where to Hang Out in Boston for the Weekend 

Recently, I took a trip with my good friend Gracie in order to explore Maine for a week on a sailboat. And yes, it was amazing. Now, being seasoned experts in travel, at eating copious amounts of food and in general good-time having, our focus was on maximizing these skills on this trip. I’ve been on a few adventures with Gracie in the past, but hadn’t really realized how well we travel together until it was just the two of us. We have similar interests, the same “old lady style” schedule and we both have that easy going, yet organized nature while on the go. 

When we were planning our travel from Toronto, she came up with the awesome idea of stopping in Boston on the way to Rockland, Maine. Our original search for flights came up with an option to fly from Toronto to New York with a stopover, then on to Portland, and then on to a bus ride for 2 hours to Rockland from there. But, with some resourceful digging and great planning skills, we discovered that we could actually fly direct to Boston on Porter Airlines from Toronto, then on to a short flight right into Rockland, Maine on Cape Air right from Boston. So, we decided – why the heck wouldn’t we want to spend some extra time travelling in Boston on the way there and back AND also lessen our travel time? Come on now. 

We each reached out to our friends and family, who had either visited or even lived in Boston before, to get a sense for what to do – but mostly for the best places to eat (because, priorities). We got a lot of feedback recommending that we hang out in the Back Bay area, so that’s where we spent most of our time. But, what we discovered during our adventures in this wonderful city, was that there are just so many cool spots to check out for the weekend!

So, let me break it down for ya. 

Where to Stay

Marriott Boston Copley

Now, if you’ve been following us for a while, you’ll know that we have a love affair with any Marriott property. It’s one of those brands that has never let us down – and they’re just freakin’ everywhere, so how can you go wrong? Set in the heart of downtown, the Boston Marriott Copley Place was the perfect location for us to explore the city in comfort and in style. Within walking distance of some great shopping, like the Prudential Centre, to Copley Square, Boston Common, Fenway Park and even to restaurants on Newbury street. 

The hotel has so much to offer for those who are trying keeping fit while on the go (or who eat their way through cities like Gracie and I do), with their high-end fitness facility and indoor pool. Equipped for the modern traveller, their bedding is super deluxe and their bathrooms are all upgraded – which is just such a luxury! Although we didn’t end up spending too much time in our room, it was an ideal and comfortable home base for us, in order to easily venture around the city. But, one of the first things that we noticed when we got to our room, was the view. The epic skyline of the iconic city of Boston was something that I had only seen in movies or TV shows. It amped up my excitement level even more than it already was – which to be honest, when travelling, is already at quite a peak.  

Where to Eat

Regina’s Pizzeria

Okay so how do you travel to Boston and NOT eat pizza? Is that even possible? Well, Regina’s came quite highly recommended. And most of the time, the lineups are out the door – but well worth the wait. They’ve been operating as “Boston’s Original Pizzeria” since 1926, in the North End of Boston. These delicious brick oven pizzas are inspired with pride by the love of good food. In true traveller-style, Gracie and I decided to order whatever the server recommended that we try. And thankfully, she suggested one with a lot of veggies on it – as we were likely in need, considering how much we were planning on eating during this trip. Let me tell you, it did not disappoint. It may actually have been one of the best pizzas I’ve ever had. And the atmosphere felt so authentic. Two giant pizza-filled thumbs up for this one, folks.

Luke’s Lobster

No visit to Boston – or anywhere in New England really – is complete without eating all of the lobster. So, our first visit for lobster roll #1 (yes, we had another one right after this one), was to Luke’s Lobster. Just around the corner from the Boston Public Library and the Boston Marathon finish line, we may sure to pay a visit to their Back Bay location. With a focus on serving traceable, sustainable lobster, crab an shrimp rolls, they’re known to deliver a great meal for a great price. And let me tell you, we were pretty darn satisfied.

Yankee Lobster Company

Now, onto lobster roll #2. Pre-gaming food with more food, my friends. Gracie is a a true champ and convinced me (with not much convincing needed), to test out another roll after our first one. Now, you can guarantee that there is usually a line-up out the door for this place – and for good reason. Located right on the water in the Boston Seaport district, it’s far from fancy – so don’t expect the finest cutlery or Michelin Star service. But, for what they deliver, they deliver it so freakin well. This is hands-down the best lobster roll I have ever had. The highlight was that you could get your lobster cooked in butter and then put on the roll. Heck yes. And it came with fries (because, more carbs please) and a bunch of different sauces or spices to add to it – should you desire. But not only do they serve up some delicious food, they also sell fresh seafood for you to take home and cook for yourself. Yankee for the win!

Flour Bakery

This place came highly recommended, so it was one of our first stops. And then it turned into our most frequented spot during our time in Boston. I think Gracie and I can both agree that we’re a bit obsessed with this bakery. Known for their delicious baked goods (and more specifically, their banana bread), they also serve made-to-order sandwiches and salads. Their breakfast sandwich is something that we went back for twice – it was just that good. And not only is their branding super cute and their coffee ultra-yummy, but their staff was wonderful and their cookbook is a must-add to your collection. 

Myers + Chang

Another restaurant that came highly recommended, this Asian-fusion venue offers incredible food in a funky indie-diner setting. The vibe was amazing, but the food was actually next level. Every course we ordered (because we ordered a whole bunch of them) was fresh, fragrant and beautifully crafted. Chef/Owner Joanne Chang and Executive Chef Karen Akunowicz offer a very personal interpretation of Chinese, Thai, Taiwanese and Vietnamese specialties. I think I speak for both of us when I say that the Cold Taiwanese Dan Dan Noodles were our favourite dish of the night (but they were pretty darn spicy, so watch out). Gracie ended up buying their cookbook and then had us over for dinner one night when we got home, so that she could re-create these noodles and a few other meals from book… and they were still so incredible. I highly recommend that you check this place out. 

Juice Press

So, if you decide to go on an eating tour of Boston like we did, you may want to also find a bit of balance. And that’s why we made a quick pit-stop (in between all of the food) in order to hydrate and get in some quick greens and superfoods. Being a Nutritionist, you would think that I’m super into places like this. But, I’m not usually, to be honest. I feel like eating the whole food itself is usually the best option. Although, sometimes you find a place that is doing a really great job at creating a one-stop-shop for wellness and nutrition. Juice Press has a great selection, with a variety of different products for every need. They also serve homemade foods, smoothies, açai bowls and supplements. 

Where to Shop


Now, you would think that when I say “shop” that I mean clothing. But nope, we’re back to food again. My obsession with Italy and all things Italian is nicely bundled together, all in this one place. The sights, the smells, the tastes… everything is magical here. From food, to wine, home and beauty, you can fill your home (or your belly) with everything Italian. Located in the Prudential Centre, you can either start or end your trip here, while shopping around the rest of the amazing mall. 

Vintage stores

In between eating non-stop (have I mentioned that yet?), we did actually spend some time wandering around to some of the cute little shops down each side street. What we found, was that there are lots of hidden gems around every corner. Maybe it was the excitement of being in a new city or even in a different country, but it’s pretty wonderful to discover all of things you can find. From designer to vintage, there are spots all over the city! 

Where to Check Out

Walk Around Some History

If you’re not so much into food (and I need to know why, because… food), but are a true history- or architecture-buff instead, you will love this city. Known as a walkable-city, you can easily get around to check out the National Historic Landmarks, which includes 57 designated properties and districts. Here’s a great list for you to check out, in order to get started on your historical journey of exploration! 

Walk Around the Waterfront

Now, it’s no secret that Boston is located right on the water. And they’ve done such a wonderful job on the development of the area – with places to eat, shop and play. To check out the whole waterfront, you can stroll along Boston’s Harborwalk, which has 40 miles of pedestrian and bike-friendly public access right at the water’s edge. 

Take in Art Installations or Parks

In between our meals, we spent some time exploring a few of the parks in the area. We even stumbled upon some that had art installations, markets, food stalls and more! For such a big city, it’s nice to see that they’ve made a commitment to keeping a fair amount of green space. The Boston Parks and Recreation Department ensures that they create and maintain clean, green, safe, and accessible open space in more than 2,300 acres of park land throughout the Boston area.

Whether you’re a foodie (like us), a history-buff or you just want to check out a new and exciting city, you’ll be spoiled for options if you add Boston to your must-travel list. Now that you know where to stay, where to eat and what to do – you’re all set.

Bon Voyage! 

Also, be sure to follow along with my Instagram account! For more information and helpful tips, make sure to stay up to date with all things Health & Nutrition on my website, Catherine’s Cabinet.

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In health,
Catherine Sugrue, CNP
Holistic Nutritionist


Photos by Catherine Sugrue

Photo of Myers + Chang taken from their respective Facebook Page 

*Please note that this is a sponsored post – our disclosure can be found at all times by clicking here.

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