Published September 3, 2022

Since we already explored Boston’s North End, we decided to start our day with breakfast in Back Bay before taking the train up toward the Waterfront and Financial District.

Thinking Cup

I researched Thinking Cup before we arrived in Boston and added it to our list of coffee shops to visit. We stopped by the Newbury Street location, though there were two other locations in Boston.

According to their website, Thinking Cup says they were, “The first coffee shop in Downtown Boston to serve "Stumptown Coffee" which originated in Portland, Oregon and was named "Best Coffee in the World" by NPR, The New York Times, Food & Wine Magazine, and USA Today.”

I figured with that much hype, we had to stop in for coffee at some point during our stay.

Thinking Cup Newbury | Interior Design

Thinking Cup on Newbury was designed similar to the other businesses on Newbury Street, where you went downstairs to enter the business. What was interesting about the Thinking Cup was that you passed the pastry case and seating before going down more stairs, where booth seating and the coffee counter were.

We went downstairs to the coffee counter. I felt that it was an odd layout to not have the menus displayed behind the coffee counter when ordering. We turned our backs to the counter to try and read the pastry options. In the end, we stuck with a simple blueberry muffin, which we saw on our way in and moved down the length of the counter to collect our coffees.

I wanted a caramel iced coffee, but Thinking Cup only offered flavored lattes so I ordered an iced latte. My boyfriend got a chai latte. I believe our drinks were $3.95 and $4.95.

A few patrons sat in the booth seating along the right hand wall. Most people sat outside. Thinking Cup had a clean, slightly elevated vintage style, which I enjoyed.

After collecting our coffees, we went to the booth and table seating at the top of the room, near the exit. I forgot to take a picture of our coffees, but here was our blueberry muffin, which was tasty. It had a generous amount of blueberries and a crispy coating of sugar across the top.

I feel Thinking Cup Newbury was a nice coffee shop to stop into, but there was nothing about their coffee (for me) that made me feel like it was the best coffee I’ve ever had in my life.

Next time we visit Boston, I hope to try their food items, so I can write a full restaurant review of their offerings.

Visiting the Boston Waterfront

Since we already walked the Boston Common and North End, the next section of Boston to visit was the Financial District and Waterfront. We took a short subway ride to the South Street Station and started our walk from there.

This section of Boston had the tall beautiful buildings I expected to see in the city.

We started at the beginning of the Rose Kennedy Greenway near Dewey Square and followed the path parallel to Atlantic Ave.

Early in our walk we passed by volunteers tending the garden in front of this open grassy area. A mural decorated the space, where a circle of red Adirondack chairs waited to be used. I loved the decorative artwork and the clean open spaces for socializing.

The Rose Kennedy Greenway alternated between a gravel path and concrete. Framed by trees and greenery, signs tucked between the plants talked about the organic treatment that supported pollinators. Occasional art installations decorated the greenery.

Atlantic Ave was busy with people but the greenway, since it was mostly in the sun, was bare of people except for a lone couple behind us and the occasional runner.

Color Commons

Eventually we made it up to the Color Commons.

A sign on the sculptures instructed that if it was dusk, we could text a color to the given number and have an interactive art display and see the sculptures change color. I thought that was fun, but given it was the middle of the bright summer morning, we couldn’t participate in this interactive sculpture.

We continued along our path, passing water fountains where children of all ages dodged between the spurts of water, which was welcome given the direct sun at this time of day.

I even noted the public hand sanitizer stations and manicured walkways in this area. I loved the architecture of the buildings and that this section of the city wasn’t crowded with groups of tourists.

On the other side of the street, crowds of families walked in the direction of the Boston Aquarium and whale tours. Luckily, my boyfriend and I were on the same page that it wasn’t worth the time in our short trip to spend half the day on a boat for whale watching.

We continued along the path and passed The Greenway Carousel before crossing the street into the share of the Christopher Columbus Waterfront Park.

We walked through the Rose Kennedy rose garden, which had colorful flowers blooming within the protection of a fence. A trellis caught our eye farther ahead so we followed the wide path down to its shade.

Two or three people lounged on blankets in the hot summer sun. A cool breeze greeted us now that we were near the water. We rested under the trellis for a bit, noting the nearby buildings and architecture before walking closer to the waterfront (Long Wharf North). I could see the bottom of the water and a few fish.

As unplanned as it was to find the Make Way for Ducklings sculpture in the Boston Common, we also found the Waterboat Duck House.

Four ducks sunned themselves on their dock. Fresh water poured into a bowl and a little house offered them shade from the heat. I thought this was a fantastic idea from whoever built this dock for them.

We followed the planks of the Harborwalk, stopping at the open area of the Long Wharf to look out on the sailboats. It was the perfect summer weather and this area of the Harborwalk was not as busy as it was near the aquarium.

We rested on a bench in between the Simons theater and Freedom Boat Club Building. Our bench faced the water and we could watch the boats farther out and listen to the live Jazz music coming from the sidewalk in front of the aquarium.

Our goal for the day was to explore the rest of the South Boston Waterfront and find a restaurant for a seafood lunch.

Boston’s Chinatown

Have you visited the Boston Waterfront? Do you have a favorite place in the area that you’d recommend I visit? Leave a comment below with your recommendations.

Are you ready to read our adventures in South Boston’s Waterfront and lunch in Chinatown? Click here to read my next post from our travels in Boston.