4 days in Boston, MA...what to do? UPDATE

Hubby’s company is sending him to a conference in Boston in October, and I get to tag along. We will arrive early on Sunday, and leave late on Thursday. We will have a rental car. Neither of us have ever been there. What are the must-do items you would recommend? He will have most afternoons free, since he only has to attend morning seminars for Mon- Wed, and we will have Thursday morning free until we have to be at the airport by 3.

Wow, lots of great suggestions here! Thank you all! I’ve been scouring Trip Advisor for ideas, and have seen many of these mentioned, but it’s hard to decide without input from folks who have been there.

I’m thinking I’d like to do the aquarium, freedom trail, ride the ducks, and Quincy market for sure. I’d love to do whale watching, but not sure if we’ll be able to fit it in.

Restaurant recommendations are also greatly appreciated! :D

I live fairly close and love Boston!

Your plans look good to me. The aquarium is one of my favorite places, and they just re-did the giant tank recently. The Freedom Trail will definitely hit the highlights, and the Duck Tours are fun. Quincy Market is shopping and a lot of food stations, so you could double that up with one of the other activities to free a day for a whale watch if you want to. (I've only done one in summer, though, so I don't know anything about how much you'd see in October.) The Blue Hills are very close, too if you want to take a short drive to see some fall color.
 
I’d love to do whale watching, but not sure if we’ll be able to fit it in.

When you get to October, there aren't as many times scheduled during the day. I've done whale watches through the New England Aquarium and I checked their schedule. The only go out at noon from the end of September on. The later it is in October, the less likely you are to have whale sightings since they'll start migrating to warmer waters.
 
Thank you YachtClubWoman and seshat0120 for the Newbury Street shops info!
 

Where exactly, and what time, is the conference? Eighteen miles at rush hour is going to require him departing very early each day.

The conference is at the Marriott in Burlington, so all of the hotels we had as an option were close by. :thumbsup2
 
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Jumping in on this because we're heading to Boston next week and I'm working out how we're going to be spending our afternoons as well (mornings are all about college tours). We're staying at a hotel near the Quincy/Adams red line stop and will have a car that we'll only be using selectively. We'll have three afternoons free - Sun, Mon, and Tues - for sightseeing, but I don't have specific destinations in mind yet. I know DD wants to see Walden because we missed it the last time we were in the area, but the rest is up in the air.
 
The conference is at the Marriott in Burlington, so all of the hotels we had as an option were close by. :thumbsup2

Let me know how you like the Cape, I lived there 30 years..
Chatham Lighthouse is a halfway point, Exit 11... a very beautiful area!
Enjoy
 












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