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Boston Itinerary in October? Help for our researched trip appreciated!

Thank you in advance for help and feedback.

We are arriving in Boston late Thursday in October and will be going to Salem to visit PEM and stroll for a day on Friday.

Friday the 5 of us will have dinner in Boston. We are staying at the Taj Boston.

Saturday we plan to brunch and hit the Freedom Trail. My husband and I are doing a "date night". High on the list is No 9, Troquet, and Erbaluce. We did tasting at L'Esplier several visits ago.

Sunday our plan is for an early brunch at ICOB with a visit to the Isabella G. Museum and casual early family dinner.

Myers and Chang, Shojo, Toro and possible Prezza are all on our family dining list. Although I feel like we are short on Boston "Italian". We did Pizza Regina in NE for lunch our last visit and don't need to go back.

Again, I appreciate all feedback and help. h

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  1. Which weekend in October? October contains the Head of the Charles Regatta when Boston is flooded with rowers and their friends and family, and most weekends in October are visiting parent weekends for various colleges, giving particular areas of town to avoid depending on which college is up that weekend.

      1. La Morra in Brookline is family-friendly and has half-order pastas, so that is an option if you decide you want more Italian. The food is very good.

        1. Don't leave Salem before visiting Turtle Alley chocolates on Essex St. just down the block from the PEM.

          http://turtlealley.com/

          1. Salem and especially PEM are great destinations, but late October attracts huge tourist crowds to the city, mostly related to Halloween.

            I'm not discouraging the visit at all. Just make sure you factor this into your transportation plans. Traffic and parking can be tough. You might want to consider the commuter rail from Boston. The Salem station is just a few blocks from PEM. It is also very close to Federal and Chestnut Streets, which are beautiful.