The purpose for my trip to Boston was to meet my friend Matt and go see Pearl Jam in concert at historic Fenway Park. We originally got tickets to the Tuesday show and planned to fly in Monday afternoon and back home Wednesday afternoon. We then realized that it made more sense to fly in on Sunday and try and get tickets to the Sunday show as well. It didn’t cost us anything to change our flights and the additional night in the hotel wasn’t too expensive.

We arrived in Boston Sunday around the same time from different cities. We shared an Uber to our hotel, the Hyatt Regency Boston (review to follow). That afternoon, we met up with my old friend and his wife near Faneuil Hall for an early dinner and then we took the T over to Fenway for the show. We had a great time at the concert and our seats were very good (although a bit far from the stage).

After the show, we took the T back to the Hyatt and crashed. It had been a long day with travel and standing for the whole show. We’re not as young as we used to be!

On Monday, we took a bike tour around Boston. In my many previous visits, I had done a walking tour, a beer tour (with Matt on a previous guy’s trip with another friend of ours), a segway tour and a trolley tour. The bike tour nicely complimented all of these as we saw a lot more of the city, including Beacon Hill, Boston University, and different areas along the Charles River. We also went back by Fenway Park again.

The tour was booked through Urban Adventours and I highly recommend it, especially if you have great weather like we did. They offer e-bikes if you don’t feel like pedaling uphill. We did the 10am tour and went back to the hotel afterwards to rest up a bit.

That evening, we went to the Encore Boston to gamble a bit and watch Monday Night Football. The resort was a bit outside of town and we took an Uber there. It’s very much like a Vegas casino (obviously managed by the Wynn/Encore group) with a huge casino floor, several different (overpriced) restaurants and a huge hotel.

We didn’t really gamble much as we both joined the rewards program and used our $50 in free bets for a few hands of blackjack (for me) and a few rounds of roulette (for Matt). After that, we had dinner at the Asian restaurant and then watched the first half of the football game in the sportsbook. I had joined BetMGM when I landed in Massachusetts (as there’s no sports gambling in Georgia yet). We made a few interesting bets on the app which we followed through the game.

We went back to the Hyatt to watch the second half as we knew we’d have a long day on Tuesday. In the end, we won about $20 betting on the game so who says everyone loses at the casino?

On Tuesday, we went over to Fenway around 11am so we could try and buy some Pearl Jam merchandise. We both got the set-list T-shirt from Sunday night. Afterwards, we had a great lunch at Thornton’s near Fenway.

After lunch, we walked about 45 minutes over the bridge to Cambridge to the Phoenix Landing where we watched the Liverpool v. AC Milan Champions League match with the Boston Reds. It was a lot of fun watching with the group and Liverpool won 3-1.

While we were sitting at the bar, I ended up buying field-level seats for the show as the prices had come way down. We weren’t able to sell our original seats, but even factoring in that amount, we paid a reasonable price for much better seats. We had checked out the location of our original seats when we were there Sunday, and they had a huge pole blocking most of the stage view.

We had planned to rideshare back to Fenway after the match, but there was some serious surge pricing going on. As the weather had cooled off, we decided to just walk back to the ballpark.

The show on Tuesday was just as good or perhaps even better than Sunday’s. The field seats certainly provided an even better view. As is customary with Pearl Jam, the show was almost a completely different set list from Sunday, hence the value in seeing both shows.

After the show, we took the T back to the Hyatt. The next day, we had some free time in the morning before we had to head to the airport. We decided to walk over the bridge toward Bunker Hill and visit the USS Constitution, a 200-year-old ship. We also visited the small museum there and the WWII gunboat that is also part of the same National Park area. The ships and museum are free to visit with a suggested donation of $10-15.

From there, we walked the short distance to Bunker Hill and walked up the monument. It was 294 steps to the top which had some nice views of the city.

At that point, I was exhausted from walking over 15,000 steps (including the up and down ones) two days in a row. We grabbed a Lyft back to the Hyatt and packed up for our flights home. We had a great trip to Boston, combining two amazing Pearl Jam shows, some history and some outdoor exercise in the great weather.

Up next: A review of the Hyatt Regency Boston.

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