New England Fall Foliage Trip Day Two: Exploring Boston

Blue skies and brilliant sunshine greeted us for our first full day in Boston. After a hearty breakfast in our hotel room, we made the short jaunt around the corner to the bus station and two quick routes later we disembarked in front of the Aquarium.

Even though it’s a touristy thing to do, we love starting our time in new cities with a hop-on-hop-off bus tour to get the lay of the land and make note of places we want to revisit later in the trip.

The Hop on Hop Off Old Town Trolley Tour seemed like the best deal, even at the steep $45/person tickets. We waited until we got on-site to purchase the tickets and were able to get a better deal than the discounted internet price just by mentioning the online savings. We ended up saving almost $30!

The tour lasted around 90 minutes and included 15 official stops (several were closed for various reasons) and many additional points of interest along the way. Our driver was animated and full of interesting tidbits of history.

Once the tour was over we were ready to stretch our legs and continue our explorations on foot. We traversed the famed Faneuil Hall Market area and picked up The Freedom Trail (a narrow red brick inset in the ground that covers 2.5 miles) to Hanover Street.

Dozens of restaurants line the street of what is essentially considered Boston’s Little Italy, hence pasta and pizza places galore vied for our business. But I already had one flagged on my trip ideas list, so we navigated to Galleria Umberto.

A friendly man stood at the counter with a sheet pan of pizza, serving out a piece or two at a time to a line of customers that moved quickly through the door. At $2 a slice, we didn’t hesitate to order one for each of us, along with a $6 spinach, cheese, and sausage calzone to share. Everything was clearly gluten-laden, so we ordered our food to go, forked over the $12 cash (they are cash-only, which, we discovered to our surprise, is not uncommon in this part of Boston at some of the more famous eateries), and went in search of a spot to eat that offered gluten free fare.

We didn’t have to walk far before a sandwich board announced gluten free pasta and pizza options. The hostess at BenCotto cheerily agreed to seat us at a table even though only one in our group would be ordering from their menu while the rest of us indulged in our previously acquired items.

With renewed energy, we continued our walk along The Freedom Trail, past the unassuming Paul Revere house, St. James Church, and Copp’s Hill Burying Ground.

Eventually we arrived at the Charlestown Navy Yard where we toured the USS Constitution. The oldest commissioned ship in the United States Navy is part of the National Park Service, and self-guided tours are free of charge.

We climbed up and down the decks and enjoyed imagining what life must have been like on these massive vessels for weeks on end at sea. Probably not something I want to find out via personal experience!

On the other side of the pier the USS Cassin Young was also open to visitors. The World War II destroyer was assigned to the Central Pacific and served a crucial role in the war against Japan. She suffered a damaging and fatal kamikaze hit just 16 days before Japan surrendered, killing 22 of her crew members. It’s fascinating to learn bits of history, and we are grateful for those who have devoted time and energy to preserving it for us to experience.

Boston is home to numerous cute little cafés and bakeries. We were ready for an afternoon coffee and pastry break, so it was just a matter of figuring out which spot to try today. We settled on a Tatte Bakery & Café that is housed in the historic Charles Street Meeting House.

We had a hard time choosing from the delectable array of pastries and desserts, but eventually made our decisions and savored the goodness while sitting on the steps on the side of the building. A flock of daring birds joined us and got a few nibbles of their own from the hands of certain ones in our group who enjoy feathered creatures…

After our afternoon snack, we meandered through the Beacon Hill neighborhood, stopping for a few pictures at the iconic Acorn Street (one of the most photographed streets in the country!).

We were especially enamored with the many artistically and seasonally arranged window boxes that adorned the homes along the way. This was one of our favorites!

Our walk took us through Boston Common, the oldest public park in America.

A quick T ride took us to the Seaport District where we walked along the pier as the sun set over the city. What a gorgeous fall evening!

Aceituna Grill was our dinner spot. We enjoyed the fresh Mediterranean selections while our phones charged and our feet got a reprieve from several hours of walking.

One final walk of the evening took us back to a bustling Hanover Street for some creamy gelato. Because when you’re on vacation 2-a-day desserts are perfectly acceptable. 🙂 Caffé Paradiso served up their housemade flavors, leaving us duly satisfied (although the consensus was that it wasn’t quite as good as our local Cocoa Dolce gelato) and ready to call it a night.

We walked back to the rail line under the bright lights of the Boston skyline and a few stars that were bright enough to outshine them. Couldn’t have asked for a better day to explore the charming historic city of Boston!