A Byers’ Guide to Boston, Massachusetts

Jake and I recently took a trip to Boston, Massachusetts during his vacation week. I had never been and Jake had only briefly been for a residency interview. Since Jake had a vacation week in October, I wanted to pick a destination with fall weather and that might have fall foliage already. We lucked out and got to see some early foliage; I bet by now the leaves have completely changed. We picked Boston since there is a ton of history. Since we had 5 nights, I kept our agenda very laid back. We accomplished everything on our list and more.

How Long We Stayed:

It was definitely nice to be able to leisurely explore Boston, but we would have still been able to do everything on our agenda in 3-4 nights. Boston is a smaller major city and a lot of the attractions are close together. It’s easy to quickly do a lot there, unlike somewhere like New York or Los Angeles. I would recommend 3 or 4 nights, depending on if you would like to make a day trip to one of the other attractions (Salem, Martha’s Vineyard, etc.) in the area.

Where To Stay:

We stayed in Copley Square and it was the perfect central area. We had a lot of good shopping and restaurants near our hotel. I highly recommend staying in this area!


Boston is very walkable, so I was glad we didn’t rent a car. For places that were not as close, we Ubered and we also took a quick commuter train to Salem one day. A car is not necessary unless you want to venture out to nearby cities that are not close to a train station.

What To Do:

  • Explore Beacon Hill: This is probably my favorite area we saw and is home to the famous cobblestone road, Acorn Street. I loved strolling the area, looking at little shops and gorgeous homes. If you’re looking for a place to eat, I highly recommend Tatte Bakery. Outfit details here.
  • Walk The Freedom Trail:

    Taken near the Massachusetts State House

    Although the Freedom Trail is supposedly only 2.5 miles total, it feels much longer than that. We walked around 8 or 9 miles that day, and it definitely felt like the trail comprised about half that total. We spent over half of the day doing this, since there are so many huge landmarks to see. We started off at the Massachusetts State House, and from there we saw where Benjamin Franklin’s parents are buried, The Old North Church, Paul Revere’s Home, The North End, Bunker Hill, where the Boston Massacre took place, and many areas where significant events in American history occurred.

  • Charlestown: The homes are also gorgeous in this area. I enjoyed exploring this area near the Bunker Hill memorial.
  • Explore North End Aka Little Italy: We explored this area during the Freedom Trail, but it was worth going back. Although we didn’t have Italian food there, it would be worth it. I recommend getting a cannoli at Mike’s Pastry and a lobster roll at Neptune Oysters.
  • Boston Public Library: The most gorgeous public library I’ve ever seen! The architecture is amazing. Outfit details here.
  • Boston Public Garden: The fall foliage was just starting to appear. This is a great spot for photos.
  • Back Bay Area: This was near our hotel and I found some gorgeous homes. There is a lot of good shopping, from middle range stores to high end places like Prada, Gucci, and more.
  • Copley Square: This is where our hotel was located and it was the perfect area because we were a quick walk from shopping and many other great areas in the city.
  • See The Ether Dome at Massachusetts General Hospital: If you’re in the medical field or love learning about medicine, Jake highly recommends seeing The Ether Dome,  the site were the first surgical anesthestic was administered.
  • See Harvard’s Campus: We ventured to Cambridge, where Harvard University is located. I enjoyed seeing the gorgeous campus. Harvard Square also has a lot of great shopping and restaurants.
  • See Fenway Park: Although I’m not a big baseball fan, I added Fenway Park on our agenda for Jake. The stadium is HUGE and they offer tours. Sadly we missed the end of the Red Sox season by a few weeks. It would have been an amazing experience to see a live game.
  • Isabella Stewart Gardner Museum: This is an art museum which showcases examples of European, Asian, and American art. Its collection includes paintings, sculpture, tapestries, and decorative arts. My favorite part about the museum was the gorgeous architecture. I felt like I was touring a castle. It was one of the best museums I’ve been to.
  • Skywalk Observatory: This was located near our hotel as well. It was a perfect way to see a gorgeous view of the city skyline. I recommend going around sunset for the best view.
  • Walk By The Bay:  There was a lot of fall foliage starting to show up. We Ubered to Hatch Memorial Shell and enjoyed walking the area and seeing a gorgeous bay view.
  • See Where The Boston Tea Party Took Place: We didn’t go to the museum, but it was neat seeing where they think the Boston Tea Party took place (they are not 100% sure of the exact location).
  • Day Trip to Salem: I did a full blog post on Salem here, but it was the perfect time of year to visit.

Other Suggestions:

  • Duck Boat Tour: If you’re limited on time, a Duck Boat Tour is a great way to see the whole city. It’s a bus that drives around and also goes in the water. We felt like we got our whole list of things we wanted to tour done, so we didn’t do the duck boat tour.


  • Eataly: We didn’t make it to Eataly during our New York City trip, so this was high on my list. Luckily it was a 5 minute walk from our hotel and we visited 3 times. Eataly is an Italian market that features restaurants and a grocery store. The food is very authentic (I’ve been to Italy and it is seriously just like Italy; the company is based in Italy). Their pizza/pasta is some of the best I’ve had. Luckily I heard Dallas is getting one, so I cannot wait to visit when seeing family.
  • Mike’s Pastry: Their cannolis are seriously amazing!  They’re huge and I somehow managed to eat mine in one sitting.
  • Union Oyster House: This is just off of the Freedom Trail and had amazing lobster. It took a while to get in, but the seafood was great. It is pretty touristy.
  • Neptune Oyster for a Lobster Roll: I’ve only had a few lobster rolls, but this one was by far the best I’ve had. Jake and I lucked out by finding two seats that the bar. They usually have a very long wait, even for lunch.
  • Tatte: They have amazing breakfast food and bakery items.
  • Boston Public Market: This is the ultimate food hall and had so many delicious options. They have everything from pasta, to apple cider donuts, to seafood and more.
  • Terra: This is a restaurant located in Eataly and was great! It’s perfect for a date night and is very Instagramable. There are gorgeous plants all over the restaurant. We couldn’t tell if they’re real or not.

Have you been to Boston? What are your favorite spots?



  1. October 28, 2019 / 5:05 am

    My hometown is only an hour and a half from Boston so I grew up going on day trips to there and Salem. Loved following along! Your fall outfits were perfect. 🙂

    xoxo A

    • abyersguide
      November 3, 2019 / 7:55 pm

      That is so neat! I would love to live in this area. It was so beautiful. Aw thanks, friend.

  2. October 28, 2019 / 7:43 am

    How fun!! We were only in Boston for 24 hours so we missed a lot! I really wanted to see the Harvard campus and the Boston Public Library. We did really enjoy the Public Gardens and the Freedom Trail though. I’m glad you guys got a little vacation!!

    Katherine | http://www.oneswainkycouple.com

    • abyersguide
      October 28, 2019 / 2:39 pm

      It was such a great trip! Thank you so much for reading, Katherine. You’ll have to go back someday.

  3. jenniferpickering22gmailcom
    October 29, 2019 / 3:31 am

    I’d really love to go back to Boston! It’s been so long!

    Effortlessly Sophisticated

    • abyersguide
      November 3, 2019 / 7:57 pm

      Boston is so neat! I’d love to go back too.

  4. Lindsey Puls
    October 29, 2019 / 3:43 pm

    Oh my gosh, we have to get back to Boston! There is so much we missed! All of your photos are gorgeous and you seriously packed the perfect wardrobe. I also didn’t know Boston had an Eataly! My husband and I loved grabbing lunch at one in Moscow – their food is so good!

    • abyersguide
      November 3, 2019 / 7:58 pm

      Boston really is a neat city! We loved exploring. Aw thanks, Lindsey. You are so sweet. Yes, Eataly was awesome. I hear they’re getting one in Dallas, I cannot wait to visit.

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