Solo Boston Trip Itenerary

Hi friends! I’m currently sitting at a coffee shop in Boston, Massachusetts writing this blog post. This morning I was in Austin, Texas and now I’m in Boston and that just blows my mind. I’m so thankful for the invention of planes. As we all know, I love traveling and I was at the airport last weekend for a quick flight home and I suddenly missed traveling so much! I was also looking at old photos from my solo Europe trip reminiscing and it made me really want to do another solo trip. I’m about to graduate college and my classes just ended yesterday and I have about 1 week before my final class called Capstone begins and so naturally I had to travel. I figured I would just go wherever I could find a good flight deal. When I searched for flights, it came down to Boston, New York, or Cancun. Boston was obviously the winner and I’m so glad it was! My flight was around $200 roundtrip with my flight from Austin to Boston being nonstop (such a steal!!). So I booked the flight, hopped on the plane, and here I am. And I couldn’t be more happy that I did. Today was such a good day. I’m going to break down what I did in my 4 days in Boston below so keep reading to here and see all the photos!

Lodging: HI Boston Hostel

Day 1: Flight from Austin arriving in Boston at 12:30pm local time, Gourmet Dumpling House, Freedom Trail, Regina Pizza, JAHO Artisan Coffee

When my flight got in, I hopped on the public transportation that took me from the airport to my hostel downtown. It was only about a 15-20 minute ride on the bus. It was interesting because the bus had its own tunnel underground that it went through to avoid traffic. Very different than the city buses in Austin. And the bus ended up being free so that was amazing! From the station where the bus dropped me off, I walked 10 minutes to my hostel and checked in. I found my hostel on which is my favorite app/website for finding the best hostels in every city you go to! It’s a super cute hostel, very clean and modern. I’m in an 8 bed bunk bed style dorm room and as of today I just have 1 roommate. Being in a hostel again made me so happy and made me remember all my amazing memories from staying in hostels while traveling around Europe almost 3 years ago (how has it been that long!?).

At this point I was starving so I went to Gourmet Dumpling House, which was recommended by the receptionist at the hostel and it did not disappoint! I had yummy vegetable dumplings before setting off on my adventure for the day. I’m a very play it be ear type of person on trips and so I didn’t make any real plans, but I had some ideas of sites I wanted to see. I decided to start off today walking the Freedom Trail since it would take me walking over a large portion of the city so I would be able to see a lot on my first day. The Freedom Trail is a way you can walk through the city and see many historic sites along the way. The path is marked with bricks through 2.5 miles of Boston. It begins at the Boston Common Visitors Center and ends in the North End. You can pay to do a walking tour if you want, but it’s also super easy to just walk it at your own pace so you can stop for as little or as long as you want to taking pictures and reading about the history. Here are the photos from different spots along the Freedom Trail! Also I laugh because the receptionist told me walking the trail would take 1-1.5 hours and naturally, me being me, it took me 3 hours LOL. I like to walk really slow, read all the signs, take lots of pictures, and I tend to get distracted with other cool sites along the way. Also, along the way I stopped at Quincy Market and Modern Pastry (not part of the Freedom Trail technically, but on the walk!)

This was weirdly my favorite stop. It was a cemetery where a lot of people from American History are buried! I saw the grave of John Hancock, Paul Revere, and others. Most of the tombstones are from the 1600’s and 1700’s which is so crazy. A lot of them were faded which is so sad and is just a reminder that this life is not forever. As a Christian, I find peace in knowing that we are just travelers on this Earth and our final resting place is in eternity with Jesus! I absolutely respect that everyone has different beliefs, but if any of you readers ever want to talk to me about life after death, life now with Jesus, and the overwhelming peace I feel having Jesus as my Savior, please don’t ever hesitate to reach out ❤

Finally, I ended my day by walking around TD Gardens and eating dinner at Regina Pizza. This is a well known pizza place in Boston and it’s funny that I ended up there because the only other time I had been in Boston (for 1 day in 2018 with my parents) we went to the exact same place. And I didn’t even realize it until I walked into the restaurant and thought “omg! I’ve totally been here before”. I ended up sitting at the bar and got to meet the nicest people and got to chat with the bartender for a while. I absolutely love meeting new people and hearing their stories. It’s one of my favorite things about traveling! I’m becoming more like my mom every day because she never meets a stranger and I aspire to be like that. I’m definitely getting there, slowly but surely.

And now, here I am sitting at JAHO Artisan Coffee, 2 minutes down the street from my hostel typing this blog post! I’m going to be writing this blog every day to update what I have done and then posting it at the end of my trip so that is a wrap for my Wednesday. What a good day. What a good life. I’m so thankful.

Day 2: Boston Harbor, Lookout Rooftop and Bar, Boston Tea Party Ships & Museum, Boston Bruins Game

My second day in Boston was jam packed just like day 1! I started out my day bright and early at Orange Theory Fitness. There was a location that was a 10 minute walk from my hostel. If you’re not familiar, Orange Theory is the fitness gym/classes I go to that has studios all across the world. Your membership allows you to go to any studio and it’s always so fun to visit other studios while traveling! After my workout, I walked around Tufts Medical Center which was actually right next to my hostel. I couldn’t walk around the inside because of COVID, but it was still really cool to see on the outside. Tufts is just one of the amazing hospitals Boston has and it’s my dream to be able to work in one of them someday!

Next, I made my way to Boston Harbor and took a stroll on the Harborwalk and around Seaport. It was so beautiful! Then, I went to L.L. Bean to buy a new jacket because this Texan is freezing her butt off here in Boston. I also needed a solid winter jacket because I’ll be traveling in Europe again in a few months so I wanted to get prepared! For lunch, I went to the Lookout Rooftop and Bar which is located inside the Envoy Hotel. To get to the rooftop, enter through the Envoy lobby and take the elevator to the “R” level. I found this spot on a blog when I was researching what to do in Boston and it was definitely one of my favorite places in Boston! The views were amazing and the food was really yummy, too. I will warn you there isn’t a large food selection and the food is a little pricey, but there is a large drink menu and the views are worth it! (Bonus: They have mocktails if you don’t want to drink alcohol. I’m doing the 75 Hard Challenge (blog coming soon about this) and not drinking right now so the mocktail options were great!).

View from the rooftop!
These sliders and sangria mocktail was so good!

After the rooftop, I did the most basic tourist thing ever, Boston Tea Party Ships & Museum. But how can you go to Boston and not visit the place that we learned about in American history class probably like a million times? It was definitely overpriced, but it was a cool experience. The guides are all in character and dressed like they are from the 18th century. The tour lasts about 1 hour and is essentially a reenactment of the Boston Tea Party with history thrown in of course. You go on a replica of the boat the tea was on, get to experience throwing the tea overboard, learn about the history, and watch a short film at the end. At the end of the tour, you can visit Abigail’s Tea Room where you can try a variety of teas as well as other drinks and pastries.

Finally, I ended my night my favorite way-at a sporting event!! I got to attend the Boston Bruins game and I had the absolute best time. The bruins won and I made more new friends with the people sitting next to me. They were so sweet and I had the best time hanging out with them! And that was my second day in Boston. I’ve had such a great trip here so far.

Day 3: The Friendly Toast, Boston Public Library, Mapparium at Mary Baker Eddy Library, Fenway Park tour, Harvard University

I started my third day in Boston at Orange Theory again. Once I got my workout in, I headed to The Friendly Toast for brunch. I had also read about this place on a blog. Another perk of being alone is getting into restaurants quicker! The wait was at least 30-45 minutes for this place, but because I was alone I was able to be seated at the bar and get in right away. I had the make your own omelet with sweet potato hash and toast (yum!). After brunch, I walked around Back Bay and went inside the Boston Public Library and some of the shops in the area. Then, I went into the Mary Baker Eddy Library to check out the Mapparium which is a large stain-glass map of the world! It was really cool to see in person, but unfortunately pictures were not allowed inside the mapparium. It cost $6 to have a short guided tour (about 20 minutes total) of the mapparium.

Inside the Boston Public Library
Inside the Mary Baker Eddy Library

In the afternoon, I headed over to Fenway Park to tour the historic stadium. Hearing about the history of the stadium was incredible. It’s so much smaller than you would imagine and smaller than most baseball stadiums. If you’re ever in Boston, I would absolutely recommend doing this tour. I hope next time I’m in town, it’s baseball season and I can go to a game! Finally, I ended my Friday walking around Harvard University and trying to fathom how anyone is smart enough to go there. Honestly, kudos to all those people. Then I got to go to a Christian gathering near Harvard and I had the best time singing and fellowshipping with other believers! The last 3 days have been non-stop and I am exhausted, but I’m so glad I was able to fit so much into this short trip.

There was a top golf event going on at the stadium which is why you see all those circles on the field (LOL)
View from the Green Monstah
The beautiful Harvard University campus

Day 4: Boston Common, Thinking Cup Coffee, Mass Gen Hospital, Flight @ 7PM-Boston->Austin

By day 4, I was pretty exhausted so I decided to just take it easy! I slept in a little bit, checked out of my hostel, and walked around the Boston Common park. In the afternoon, I hung out at Thinking Cup Coffee and took a walk over to Mass General Hospital. Finally, in the evening I headed over to the airport. My flight back wasn’t nonstop so I had a layover in Atlanta and ended up getting home around midnight. Overall, I had an amazing trip and I’m SO glad I decided to go! It made me so excited to start taking more little trips like this next year when I’m a nurse. If you made it this far, thanks for reading!!! Comment with any questions for me about Boston 🙂


Texan On The Go

7 thoughts on “Solo Boston Trip Itenerary

  1. Great trip, Kaylee! I’m so glad you have this love of adventure and travel. It’s the best!!! Thanks for sharing it with us. Here’s to many more!!

    Liked by 2 people

  2. Great reading, Kaylee. Sounds like a great trip and you do so well getting around. It sounds like you really did get a lot in for your short stay. Love reading the blogs and so happy you continue to do them. Keep them coming with your other adventures. I’m also happy that it appears you may have influenced Megan to do her blog as well. Hugs and much love, Grammy

    Liked by 1 person

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