• Home
  • About Me
    • Privacy Policy
  • Categories
    • About Me
    • Books
    • Goals
    • Life
    • Recurring Series
  • The Friendship Paradox
  • Travel
    • Asheville, NC
    • Cruising
    • San Juan, Puerto Rico
    • Savannah, GA
    • Ireland
    • Boston, MA
    • Chicago, IL
    • Niagara Falls
    • Email
    • Facebook
    • Instagram
    • RSS

Stephany Writes

Categories: Travel

New England Road Trip | Three Days in Boston

We started our New England road trip in Boston, MA. I visited Boston with book club in 2019, but my mom had never been, so it was a great starting spot for us. I enjoyed returning to this city that I really loved, and getting to do some things we didn’t get around to the first time around.

Here’s what we got up to!

Trident Booksellers

After dropping our bags off at the hotel, our first stop was a bookstore. Trident Booksellers was a 10-minute walk from our hotel, and the brewery we wanted to go to didn’t open for another hour, so it was a no-brainer. Trident is such a cool bookstore where I found yet another gorgeous copy of Anne of Green Gables to add to my collection, along with an Agatha Christie mystery. They had a great curation of books, bookish items, games, house decor, and Boston souvenirs. I opted for two books and a sticker!

New England Aquarium

Our next stop was Trillium Brewery, but when we arrived, there was a sign saying they were closed for a private event. WAH! We walked over to the Boston Public Market for a quick lunch, although it wasn’t really our scene. (A great spot if you’re a foodie, though!) We found a burger shop and called it a day. I just needed to eat something and a burger and fries sounded great to me.

After getting some sustenance, we headed over to the New England Aquarium. My mom loves visiting aquariums whenever we travel, and this one was definitely a must-visit. There were sea lions, penguins, stingrays, and huuuuge sea turtles (my mom’s fave!). And, of course, lots of fish and small sharks and all that jazz. We spent a lot of time with the penguins and also happened upon the sea lion exhibit right as the trainers were giving a speech and letting the animals show off their skills, so that was a lot of fun! We spent a few hours at the aquarium, and once my mom got an alert that our room was ready to check in, we high-tailed out of there so we could get off our feet and RELAX.

Boston Public Garden/Beacon Hill

Our first full day in Boston, we did a lot of walking! We walked Boston Public Garden, part of Boston Common, and Beacon Hill, which are all located in the same little square. I enjoyed perusing the stacks at Beacon Hill Books, although I didn’t see anything I really wanted to buy. What they did have were some copies of Emma M. Lion. I’m starting to collect physical copies of these books, and while I was hoping to snatch up the second volume (I had already purchased the first volume), the closest I could get was volume four. Oh, well! It was something, at least!

Acorn Street

In my Boston research, I kept hearing about Acorn Street, which is supposedly one of the most photographed streets in the United States. TBH, it was… fine? I mean, it was definitely gorgeous, especially in the fall, but it didn’t blow me away. However, I did force my mom to take some photos with me. Of course, every other tourist in Boston decided they wanted their pictures as well, and they didn’t seem to care that they were in everyone’s way! Ah well. That’s the magic of technology. I removed the background characters from my photo, and voilà! It’s like we were the only ones there. Muahaha.

Bull and Finch Pub (aka, the Cheers bar)

This was a must-visit for us, as my mom loved Cheers (and I watched a few seasons myself, and enjoyed them!). We stopped here for lunch, even though there was a wait. We poked around the gift shop, took some pictures outside, and eventually our table was ready. The food was surprisingly good! It’s pricey, as you might expect for a tourist trap like this, but my mom and I split a plate of chicken tenders and fries, which was a great decision. It was all very tasty!

View Boston

We picked sunset tickets for our View Boston experience, and it was a gorgeous way to end the day! We took a stroll around the place, and got lots of great daytime pictures, and then we found a couch where we could relax and watch the sun go down on the city! It wasn’t until after sunset, as we were walking downstairs to get to the elevator, that I learned there was a whole second floor we could have explored and it had a full bar. Womp, womp!

Boston Tea Party Ships & Museum

If there is anywhere to go while you’re in Boston, it is here. This was, hands down, my favorite thing we did in Boston. It’s a whole experience, too, as you go through the entire journey – what led to the Boston Tea Party, what happened during the actual event, and how it set off a chain of events that eventually led to the Revolutionary War. And, of course, you get to “throw tea” in the harbor. You start in a “meeting room” for an assembly (the final meeting of December 16, 1773, which led directly to the Boston Tea Party), then go through the motions of the tea party, and then walk through a few more interactive exhibits that take you through what was happening in the colonies in the immediate aftermath. It was so cool and I loved every minute of it.

Fenway Park

We had a bit of time after the museum before it was time for our next excursion: Fenway Park! Mom and I are not baseball fans, but it was still really cool to visit this iconic landmark in Boston and hear the history of the Red Sox. It was about an hour, and there was a lot of sitting in all the different seats around the stadium: from the original wooden seats from 1934 to the Green Monster seats to the press box. I like all the sitting, muahahaha. It was a really neat experience, and I’m sure even cooler for someone who is an actual baseball fan.

Ghosts & Gravestones Boston

We had to do a ghost tour while we were in Boston! Unfortunately, this ghost tour just didn’t do it for me. I love a ghost tour that’s a mix of history with really creepy stories, and this one just seemed to have a lot of creepy stories without the historical connection I crave. We did get to visit the graves of Franklin and Revere at night, so that was cool! But it just wasn’t my favorite ghost tour, which is fine. They can’t all be winners!

Boston Quick Facts

  • When we visited: Monday, October 5th – Wednesday, October 7th
  • Steps taken: 34,556 (over three days)
  • Pictures taken: 155
  • Best sleep: Tuesday (9 hours, 3 minutes)
  • Favorite experience: Boston Tea Party Ships & Museum
  • Favorite restaurant: Bull and Finch (although the fries at Bleacher Bar in Fenway were out of this world!)
  • Favorite little moment: Making up stories about the penguins with my mom at the aquarium
  • Souvenirs bought: a mug, an ornament, a magnet, a bookmark, and three books (Anne of Green Gables, The Murder on the Links by Agatha Christie, and volume 4 of The Unselected Journals of Emma M. Lion)

Have you ever done a ghost tour? 

You may also like

About Stephany

Hi, I'm Stephany! (She/her) I'm a 30-something single lady living in Florida. On this blog, I love talking about what I'm reading, my personal life, mental health struggles, and so much more. I love connecting with readers and other bloggers, so please leave a comment or send me an email!

Comments

  1. Cate

    October 20, 2026 at 5:26 am

    Actually, that’s where Aven Franklin’s parents are buried and he put up a monument to them. But he is buried in Philadelphia.

    Reply
  2. Sam

    October 20, 2026 at 9:28 am

    I used to live in Boston, so this made me nostalgic! Although there are definitely some places you visited, that I had never been to (the New England aquarium and Cheers bar). I’m glad you had a great start to your trip with your mom, especially after all the drama leading up to It!

    Reply
    • Stephany

      October 22, 2026 at 12:17 pm

      We had a great time in Boston! I love that city. It was fun to return and feel a bit of familiarity!

      Reply
  3. K @ TS

    October 20, 2026 at 9:48 am

    Oh I love that the Make Way For Ducklings are all dressed up. My grandma lived in MA and we always visited the ducks, even when I was a kid. She used to also take me to a bookstore called Buck a Book but I guess inflation and Amazon were too much for it, as it looks like it was closed down. The other thing I always loved was getting clam chowder (chowda), going to the North End (Italian) and wandering around Harvard/Cambridge. I know you don’t run, but the paths on the Charles are also worth seeing. There are always so many things to do and it is hard to narrow it down. Despite going there several (dozens of) times, I never went to either the aquarium or the Tea Party museum!

    Reply
    • Stephany

      October 22, 2026 at 12:20 pm

      We did Harvard, the Charles River, and the North End during my first time in Boston! My mom can’t have tomato-based meals, which limits most of what the North End offers in terms of food, ha, otherwise, I would have definitely eaten there for at least one meal.

      The Make Way for Ducklings sculpture is one of my faves! They were all dressed up like they had just run a race, which was really cute.

      Reply
  4. Michelle G.

    October 20, 2026 at 1:05 pm

    Your time in Boston sounds amazing! You did so many fun things. I love how you Photoshopped the other tourists out of the photo! I especially love the photo of you at the wheel of the ship! I have never been to Boston. Now it’s on my list of places to see!

    Reply
    • Stephany

      October 22, 2026 at 12:20 pm

      Boston is a GREAT city! It’s one of those I feel like I could return to again and again and never get sick of it. I enjoyed myself a lot!

      Reply
  5. Elisabeth

    October 21, 2026 at 7:07 am

    Boston is TOP of my list of places I want to visit in the US. I don’t think I’ve ever heard someone complain about a trip to Boston. And, living on the East Coast of Canada, it’s pretty accessible for me. We’ve been largely avoiding travel to the States the last few years for… well, you know the reasons… but we might try to squeeze in Boston next summer!

    Love the fall foliage, and that Tea Party experience sounds really cool.

    Ghost tours are NOT created equal. I’ve had a few amazing ones, a few terrible ones, and a few that were fine. It’s fun to do them periodically, but they’re definitely not my favourite go-to tour. The one we did in Stockholm earlier this year was pretty good; the guide was sooo engaging (but he had a very strong accent and that made it a bit difficult to figure out what he was actually saying).

    Reply
    • Stephany

      October 22, 2026 at 10:44 pm

      Ooh, I’m excited for you to visit Boston! I highly recommend the Tea Party museum for your fam. I thought it was fascinating! And you guys will probably be able to handle the Freedom Trail. It’s looooong but you guys are pro walkers! 🙂

      Reply
  6. Jenny

    October 21, 2026 at 9:52 am

    Wow, you guys did a LOT in three days! Of course the first thing I looked at was what you’re wearing- jackets! Sweatshirts! You got some cool weather! Last October when I went up to Illinois, they had unusually warm weather (sigh). So I’m glad the weather was good for you.
    The tea party experience sounds really cool, and also Fenway Park. Growing up I was a huge Cubs fan, so I’ve been to Wrigley Field many, many times. I can see how if you’re a huge baseball, or Red Sox fan, the Fenway tour would be amazing.
    If I did a ghost tour I would want there to be history involved- creepy stories alone wouldn’t be my thing.

    Reply
    • Stephany

      October 22, 2026 at 10:45 pm

      The weather was PERFECT! It was just cold enough that we got to wear our cute winter clothes, but not enough to make us miserable. It was so nice to wear LONG PANTS every day!

      Reply
  7. ernie

    October 21, 2026 at 11:27 pm

    Wow – you slept for over 9 hours while traveling . . . like not in your own bed. That’s amazing. I’ve been to Boston twice. I love it. I did a girls weekend there for my mom’s 70th bday (so 14 years ago). Then Coach and I took the kids when we drove Lad out to college in New York. We spent 3 days in Boston and then drove to his school. I know we could find more to do if we went back. We def didn’t do the aquarium, and it looks so cool. I’ve neve done a ghost tour. Sorry your’s didn’t measure up. Looks like you had some great weather.

    Reply
    • Stephany

      October 22, 2026 at 10:46 pm

      I got some GREAT sleep on this trip, and that’s because a) I didn’t have cats jumping up and off the bed all night and b) I brought my CPAP machine with me. I was like, “Why can’t this happen so easily at home?” Oh right, it’s because I’m on vacation and not worrying about all the things I have to do!

      Reply
  8. Birchie

    October 22, 2026 at 7:39 am

    I’ve never been to Boston but it is very much on my list and I was taking notes! The only question is whether I can still squeeze it in this year or if I wait until next spring.

    Photoshop FTW!

    Reply
    • Stephany

      October 22, 2026 at 10:47 pm

      Spring would probably be GORGEOUS for Boston, too! We contemplated a spring trip but I was still having joint pain and wouldn’t have been able to walk as much as we did. Turning it into a fall road trip was a perfect alternative!

      Reply
  9. Kim

    October 22, 2026 at 1:28 pm

    OMG! Do we get to see the new AoGG?????? Exciting!

    I have never heard of Acorn Street. I need to research why it’s so famous. It looks pretty!!!

    Oh that is funny that the ghost tour was missing the history! We have done one and I loved it because of all the history and Steven was annoyed it wasn’t more spooky, so it sounds like this one is more up his alley 😂

    Reply
    • Stephany

      October 22, 2026 at 10:48 pm

      I have no idea why Acorn Street is so famous but it is definitely pretty.

      This AoGG has sprayed edges so OF COURSE IT WAS COMING HOME WITH ME.

      I think Steven might have enjoyed this ghost tour more than I did!

      Reply
  10. Lisa’s Yarns

    October 23, 2026 at 8:28 pm

    It looks like you had fabulous weather in Boston. I know that Acorn street and also felt a little meh about it. Yes it was charming but not all that notable.

    I love that you always stop by local bookstores!!

    I am not a big fan of ghosts (they kind of creep me out) so I have never done a ghost tour. Plus they happen at night typically and I like to be back in my room then!

    Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Welcome!

Welcome!

Hi, I'm Stephany! (She/her) I'm a 30-something single lady, living in Florida. I am a bookworm, cat mom, podcaster, and reality TV junkie. I identify as an Enneagram 9, an introvert, and a Highly Sensitive Person. On this blog, you will find stories about my life, book reviews, travel experiences, and more. Welcome!

About me

Subscribe to Blog via Email

Enter your email address to subscribe to this blog and receive notifications of new posts by email.

Recent Posts

  • J is for Juggling
  • I is for Inertia
  • H is for Home
  • G is for Grandma
  • One Photo Per Day: October 31 – November 6

Search This Blog

Archives

Privacy & Cookies: This site uses cookies. By continuing to use this website, you agree to their use.

To find out more, including how to control cookies, see here: Cookie Policy

Copyright © 2026 · Theme by Blog Pixie

Copyright © 2026 · Sasha Rose Theme on Genesis Framework · WordPress · Log in