Boston is one of the oldest and most history-rich cities in the United States. As history buffs, my friend Bridgette and I have wanted to travel there for a while. While discussing this destination, we had the crazy idea to take a 24-hour trip. That’s right…24 hours, no hotel room, and as much adventuring as possible. It was fun, exciting, and (at times) a little challenging. But, we would do it all over again! Below is the travel diary, hour by hour, of our unconventional trip to this bustling city.

4:00 AM- Commute to Airport/Board Flight

We started the day bright and early…4 AM to be exact. We took an Uber to the airport, made it through security, and grabbed a quick breakfast at the gate. By the time we were onboard and pushing back, it was around 6:30 AM.

7:00 AM- Flight to Boston from ATL

The flight was about 2 ½ hours, so we landed in Boston around 9 AM. We got an Uber into town, and he dropped us off at the Boston Common. It was much colder than back home (around a 30-degree difference), and quite rainy, but we were going to embrace it and make the best of our short time there. By this point, we needed an energy boost, so we stopped by Ziggy’s Coffee Bar for some much-needed caffeine and a quick snack.

11:00 AM- Freedom Trail Tour

If you have ever been to Boston, you have most-likely heard about the Freedom Trail. It’s a red-bricked line that runs throughout the city, guiding you to all the historic sites. You can follow the trail on your own, but since we wanted to learn as much as we could, we decided to take a guided tour to really get the full experience. So, we booked a morning tour with the Boston Freedom Trail Walk in History tour, and we were not disappointed! The guide was friendly, funny, knowledgeable, and (most importantly) dressed in a colonial outfit. She gave us so much information and was able to answer any question that was thrown at her. We visited many sites, including the Massachusetts State House, Granary Burying Ground (where many important people like Samuel Adams and John Hancock are buried), the Old State House, the Boston Massacre Monument, and the Paul Revere House. This tour is a must if you have the time. I recommend booking in advance to make sure you secure a spot at your desired time.

1:00 PM- Cheers

If you’re a fan of the TV show, then you’ll want to go where everybody knows your name. That’s right, you can visit the bar that the show is based on! We couldn’t pass it up, so we grabbed lunch and a good old-fashion Boston lager to warm up and rest our feet after the long, cold tour.

2:00 PM- Boston Harbor Walk/Tea Party Ships & Museum

Do you want a great view of the city and a place to easily walk by the harbor? Then the Harbor Walk is the perfect place to be. Although it had been cold and rainy most of the morning, the rain let up a bit so that we could really enjoy the experience. This is also where the Boston Tea Party Museum and Ships are located. We looked at the replicas they had floating out on the harbor, but since we were strapped for time, we didn’t make it to the museum. However, I have heard nothing but good things about it and we will definitely stop by on our next trip!

2:30 PM- Flour Bakery

Next, we headed over to Flour Bakery for some coffee (which by this point you have realized is a must for a 24-hour trip) and a famous Boston delicacy: Boston Cream Pie. This pastry was delicious and gave us just the sugar rush we needed. To me, the texture was somewhat reminiscent of tiramisu (minus the coffee). If you are looking for an authentic and reasonably-priced cream pie, this is the place to go!

3:00 PM- Commuter Train to Salem

At this point, we had seen most of the main attractions in Boston. So, we decided to head to Salem, which was about a 30-minute ride on the commuter train. Keep in mind this is a different train system than the normal metro, so you will have to buy a separate ticket. However, a roundtrip ticket was reasonable (only $15), so it was worth it to us! We arrived in Salem fairly quickly, and it was only a short walk from the station to downtown. On the way, we walked past rows of new England townhomes and beautifully-eerie graveyards. The cold, rainy weather really added to the ambiance, as well.

4:00 PM- Salem Witch Museum

Our first stop was the Salem Witch Museum, which was located right on the main square. The ticket was $13, and once we had paid we headed over to the gift shop to wait for the next presentation to start. The gift shop had everything you need to commemorate a trip to Salem, including shirts, memorabilia, books, and more. I decided on a magnet (I have a collection of magnets from all the cities I have visited) and a small print with a black cat to hang in my home. By the time we had made our purchases, we were brought into the main presentation room. Here, we sat on stools, and listened to a riveting narrative of what happened during the Salem Witch Trials of 1692 set to 13 life-sized stage sets. Although I had a general understanding of what happened during the trials, this really brought me a new understanding of the progression of events and their cultural impact on our history. After the presentation, a tour guide led us through the rest of the exhibits that highlighted the history of witchcraft, from its pagan origins to modern day. I highly recommend stopping by this museum if the Salem Witch trials intrigue you and you want to learn more about them.

7:00 PM- Bewitched After Dark Tour

After some aimless wandering around in the square, we made our way to the Bewitched in Salem store. Here they had a lot of witchy supplies, including crystals and tarot cards. We browsed their merchandise while we waited for the rest of our tour group, and once everyone was there, our guide Jeff led us around to all of Salem’s must-see spots. Although we went to countless places, I will only be sharing some of my favorites. First, we went to the Putnam House, owned by the family who was responsible for most of the convictions and sentences in the trials. Directly next to the house is the memorial for the victims of these horrible events. There are benches with each of the victims’ names, dates of death, and method of death. What I really liked about Jeff and his tour is that he focused on each victim’s humanity. Instead of going for the shocking or macabre, he spoke about each of them with such care and focused on who they were instead of just their tragic demise. Also adjacent to the house and memorial was a graveyard with some of the oldest graves in Salem. This included many of the accused and accusers, as well as their families. Here, there was a tree that was hundreds of years old and was around during the trials. It’s considered the “last living witness” to what transpired. It’s gigantic, mystical presence in the graveyard was hauntingly beautiful and serves as a reminder of all the horror that has taken place there. We then moved away from that area to see more historic sites, but also some quirky, lighthearted things, including a statue of Sabrina from the hit television show Bewitched. This added a little bit of fun to the “witch theme” of the city and broke up the heaviness of the information we were receiving. I highly recommend getting on one of Jeff’s tours if you visit Salem. He has lived in Salem his whole life, and he is a wealth of knowledge. It was one of the best and most informational tours I have been on in all my travels!

9:30 PM- Dinner

After all of that, we headed to Sylvan Street Grill to get some sustenance. I wanted to have some New-England cuisine, so I ordered a clam chowder for an appetizer. After standing in the rain and cold all day, the soup was the perfect way to warm up. I then ordered a lobster roll, and the lobster was so fresh and juicy. It was the perfect way to end a long and eventful day of exploring!

11:30 PM- Train Back to Downtown Boston

With full bellies, we walked to the train station and headed back to Boston. The trip back was quicker, because now that it was late, it was a “direct line” and there were no stops taken between Salem and the city.

12:00 AM- Go Out (The Point- food, drinks, live music, vibes)

By this time, we had a few hours to kill before we headed back to the airport. We decided to get a few drinks and watch some live music at a local restaurant called The Point. The drinks were strong, the service was great, and the music was better. It was a relaxed spot where we could spend some time and relax after a busy day.

3:00 AM- Uber to Airport

By this point, we were exhausted and just wanted to start the process of getting back home. One thing we didn’t realize was that the security wasn’t open until 4:00 AM. Therefore, we had to sit on the floor and wait it out, which was less than ideal. However, once security opened, we breezed through, grabbed some much-needed breakfast and coffee, and waited until we could board our flight, which departed at 7:00 AM. In hindsight, we should have planned it better to get to the airport closer to the time TSA opened. Learn from our mistakes!

Overall, I would say we had a successful first 24-hour trip. Boston was history-rich and exciting, and Salem was beautiful and mystical (and one of the top places on my travel bucket list). We knew there would be challenges, and we knew we would be tired after doing so much on no sleep. We have definitely learned a thing or two, which we will utilize on our next 24-hour trip. I hope this travel diary gave you some good ideas on where to go and what to do in Boston, and maybe even inspired you to take a 24-hour trip somewhere yourself.

Thanks for reading!