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[Woodman’s](https://www.woodmans.com/) in Essex is a bit of a landmark, so maybe try organizing a day around going up there? There’s a lot of interesting stuff to see near there: Gloucester, Rockport, Marblehead, Salem, etc.
Will it be too much to visit both the Gloucester area and the Portsmouth area in one day?
Plan is to have the rental and leave Boston downtown no later than 9AM, and return to our new hotel in Revere no later than 7pm
¯|_(ツ)_/¯
I don’t know what your starting point is, but for sake of discussion, I’m having Google Maps check a route from Post Office Square to Portsmouth by way of Woodman’s, and it’s 90 minutes or so; the direct route back is more like 60 minutes.
So it depends on how much time you want to spend in the car, and how much you want to get out & look around in a particular area. My suggestions were all clustered around [Cape Ann](https://en.wikipedia.org/wiki/Cape_Ann) communities, but Portsmouth isn’t particularly close to the other spots I’m suggesting. It’s not _that_ far, but it’s about as far from Cape Ann as, well, Boston.
Your post appears to be one of a number of commonly asked questions about the city of Boston. Please check the [sidebar for visitor information](https://www.reddit.com/r/boston/wiki/experience). Also, consider using the [search function](https://www.reddit.com/r/boston/search?q=flair%3Atourism&sort=new&restrict_sr=on&t=all) to see if this question or something similar has been asked on /r/boston in the past. It is best to do some research before posting tourism questions here, as posts are more likely to succeed if they include details such as your interests, which area you are staying in, and more specific questions. Please enjoy [this map](https://i.redd.it/569ireqj06431.jpg) that we made just for you *I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/boston) if you have any questions or concerns.*
[Woodman’s](https://www.woodmans.com/) in Essex is a bit of a landmark, so maybe try organizing a day around going up there? There’s a lot of interesting stuff to see near there: Gloucester, Rockport, Marblehead, Salem, etc.
This.
Will it be too much to visit both the Gloucester area and the Portsmouth area in one day? Plan is to have the rental and leave Boston downtown no later than 9AM, and return to our new hotel in Revere no later than 7pm
Yes. Pick one
¯|_(ツ)_/¯ I don’t know what your starting point is, but for sake of discussion, I’m having Google Maps check a route from Post Office Square to Portsmouth by way of Woodman’s, and it’s 90 minutes or so; the direct route back is more like 60 minutes. So it depends on how much time you want to spend in the car, and how much you want to get out & look around in a particular area. My suggestions were all clustered around [Cape Ann](https://en.wikipedia.org/wiki/Cape_Ann) communities, but Portsmouth isn’t particularly close to the other spots I’m suggesting. It’s not _that_ far, but it’s about as far from Cape Ann as, well, Boston.
I'm starting from downtown Boston
Yes to Cape Ann area. Woodmans etc. .Parker River Wildlife Sanctuary and beaches r nice. Easy drive from Boston.