
There’s a feature with flying standby where you can pick your date and your departure airport and it will tell you the “best bets” to fly to that date. They’re the destination locations with the most seats available. When my husband and I wanted to take a quick 20th anniversary trip, we used that feature and came up with Boston. I had never been there and he had only been there for a day while in college.
We left on a Sunday afternoon and got business class seats on a direct flight. We got a Lyft to our hotel and settled in for the night.
On Monday, we decided to walk the Freedom Trail. It’s a trail of bricks in the sidewalks that take you to several historic locations in the city. You can take tours, but we did a self-guided one with a $3 map from the Visitor’s Center in Boston Commons.

We did not know, but the day we went was the anniversary of the Boston Tea Party! Several of the sites on the trail are part of that story. We stopped by churches, cemeteries, meeting houses, the Boston Massacre site, Paul Revere’s house, Bunker Hill, the USS Constitution and our final stop was the Boston Tea Party Ship and Museum. Since it was the anniversary, they had actual tea that we could throw into the water!
We check out Boston’s holiday market and found their public library. It’s the location of the Boston Marathon finish line. We had dinner at a nice Italian restaurant and then saw the Boston Pops perform their holiday show that night.

On Tuesday, we had some time before catching an afternoon flight, so we visited a chapel at the Prudential Center that had relics of St. Maria Faustina, Pope John Paul II and Maximilian Kolbe. We then visited the Cheers bar and got photos of the replica set for the show. We took the train to Harvard Square and walked around the campus for a little bit and visited a bookstore. We had lunch at Gordon Ramsay Burger (delicious!) and got some cannolis from an older, local bakery to take back home.
We got right on our standby flight and got business class seats again. I would highly recommend a trip to Boston to anyone who enjoys history. It has a laid-back city feel and you can walk to most places.















