Boston Travel Guide: Fall in Boston Weekend Itinerary

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boston travel guide
boston travel guide
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boston travel guide

If you haven’t heard from my Instagram, I spent this past weekend in Boston with fellow blogger Kelly Fox! We wanted to go on a fall foliage trip and what screams “fall” more than the East Coast? I had actually never been to Boston so I was so excited to visit.

We got in Thursday night (Kelly flew from Texas, I took the train in from NYC) and stayed until Sunday morning. It was such a fun trip and I definitely fell a little in love with the city. I’m already planning a trip back! Anyway, I asked everyone I could for recommendations, and while I didn’t get to all of them, I thought I would share with you! Keep reading for my full Boston travel guide.

Where to Stay

Let me preface this by saying that hotels in Boston are pricey. I was actually shocked at the prices and would 100% recommend booking far in advance. Because of that, I was looking for a reasonable hotel that would be more centrally located. We ended up staying at the AC Marriott Boston Downtown. It was very close to the South Station train station, which was convenient for me. I’ve stayed in Marriott’s before and my parents have a membership with the hotel group. It was a nice, somewhat small hotel and the staff was excellent — our air conditioning stopped working and when we called down to the front desk they sent someone up in minutes!

I will say, next time I go I would try to find a hotel a little more downtown — North End, Waterfront, or Beacon Hill (the prettiest area in my opinion). With that being said, Boston is actually pretty small and we were able to Uber everywhere in under 15 minutes.

Where to Eat

I got quite a few recommendations on places to eat, so I’m going to share the places I went and the ones I didn’t get around to.

  • Tatte Bakery: I went here for breakfast on Friday and Saturday and it was so good! I had the croissant breakfast sandwich and cappuccino. There are multiple locations!
  • The Barking Crab: one of my co-workers recommended this restaurant in Seaport and it was adorable! Very New England, casual. And I tried a lobster roll for the first time!
  • Giacomo: This place does not take reservations and unfortunately the line was just too long, but it was listed as one of the best Italian restaurants in North End (Boston’s Little Italy).
  • Florentine Cafe: Instead of Giacomo, we ended up at Florentine Cafe and it was delicious! The portions are huge though and honestly we could have easily split an entree. I had the Chicken Marsala and Kelly had the Chicken Parmigiano.
  • Regina Pizzeria: one of my good friend’s recommended this restaurant and I had every intention of going, but ate a late lunch and wasn’t hungry enough for dinner. I will make sure to go next time!
  • S.O.B.: So this is a sports bar-type place and we went to watch the baseball game. I got the New England clam chowder and it was delicious! Possibly my favorite thing I ate!
  • Mike’s Pastry: Okay, almost everyone I talked to said to go to Mike’s Pastry or its rival Modern Pastry. Both times I tried to go the lines were outrageous. We ended up ordering on Uber Eats back to our hotel. They are known for their cannolis, which aren’t my favorite dessert. But of course I had to try. I got a chocolate chip and chocolate mousse cannoli and the verdict is that they were really good, but I absolutely would not wait in those lines.
  • Yvonne’s: Another one of my friends recommended Yvonne’s for dinner, but sadly I didn’t make it. Keeping it on the list for next time!

What to Do

There’s so much to do! I actually am already planning to go back because I don’t think I did nearly enough! On our first full day we actually rented a car and drove through Massachusetts and went to an apple orchard. The one we went to was Honey Pot Hill Farm and the apple cider donuts were amazing. We got there a little later in the day and it was clear that a lot of families brought their kids after school. So if you want to avoid that, I would go earlier.

In Boston, here’s a list of things to do! I didn’t get to even half of this list, hence my need to go back!

  • Newbury Street for shopping
  • Visit Fenway Park, the oldest active baseball park
  • Follow the Freedom Trail
  • Explore Beacon Hill (my favorite part!!)
  • Walk around the Boston Commons
  • Walk the Charles Esplanade (sooo sad I didn’t do this)
  • Sam Adams Brewery tour

Have you ever been to the city? My trip was short, but I definitely fell in love! If you’re planning a trip, I hope my Boston travel guide was helpful!



P.S. You can check out more of my travel guides here!

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