My family and I just returned from a trip out east to attend a wedding in Connecticut. I was able to wrangle the better part of 3 days in Boston into the itinerary. We actually flew Vanc. to Boston to start the 9 day trip there. The middle 3 days were in Connecticut and then the last 3 in NY. It may be the best trip we've had as a family. My kids are 17 and 19, so was a real treat to have them along, seeing sights and learning the history that we were able to take in. Being a life-long Bruins fan, I have been to Boston 2 other times to see games. This time though being summer, I was able to plan out an amazing 2 days of sightseeing in your beautiful city.
We were fortunate to take in a Red Sox game (they are my baseball team too!), and they beat the Blue Jays so I was happy; my son not so much.. It was my wife and daughter's first ball game so they found it long.. We stayed in the Back Bay area, so there was time for the girls to wander the shops; they loved that part!
I planned out the following day to take a walking tour of The Freedom Trail, following the red brick line, with stops and descriptions of the historic locations. At certain spots the kids realized the significance of the name I read, as they'd heard it before in school and now were able to soak in that they were there on the spot..
Part way through the Freedom Trail walk, the heat forced my wife to call "detour", and we headed for the waterfront to catch some cooler air. Ended up on the Long Wharf?, and after some pictures and a stop for cool drinks we were back on the Trail. We didn't quite finish it, missing Bunker Hill area and the USS Constitution.
We still had to fit in the North End; I couldn't pass up a stop at the TD Garden that included my first time seeing the Bobby Orr statue. My family chuckled when I pulled from my backpack my ORR jersey for the photos! Awesome pic for my office bulletin board..
We lunched at The Fours. Food was great, but definitely different (much quieter) than my last visit there, which was pre-game beers before a Blackhawks visit. Oh, and I had to have the Bobby Orr sandwich of course!
We toured the Garden, escorted top to bottom from the Pro Shop / Museum group. Great tour, although my son and I had hoped to get a glimpse of the Bruins dressing room - but Visitors room only; (same for Celtics)..But some great Bruins photos on display throughout the upper levels. A great day all round.
We used Uber 3 times, my first experience with it; was easy and the drivers were excellent. Everywhere we went people were so friendly and helpful. My wife's first visit to Boston, and she fell in love with it. Hopefully that transpires into further visits - which would mean more Bruins games for me!