Work vacation with good amount of free time
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Yo-yo or other?
Edit: I’ll just assume other since I’m waiting for the school bus and don’t have Boston yo-yo recs. I haven’t lived there for a number of years, so forgive if anything’s outdated.
My favorite restaurant is Sweet Cheeks Q. Yes, it’s barbecue, yes, Boston isn’t known for barbecue, but it’s awesome. Get the biscuits.
Lobster roll: Alive and Kicking.
Beer: Lord Hobo, The Publick House (in Brookline, it’s a Belgian pub), Harpoon
Experiences: Boston is highly walkable. If you’re able, I love walking up Newbury Street, through the Common, and all the way to Faneuil Hall. It’s a ways but you see a lot. On Sunday’s they close Memorial Drive to cars so you can walk or bike it.
Edit2: if you’re looking for something specific, let me know 
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If you have any access to a car, cape cod/portsmouth nh/Maine/Rhode Island are all pretty close by!
If you’re near Faneuil Hall, check out the North End (Boston’s little Italy) known for its Italian food, baked goods (a common favorite are cannoli’s), and old school grocers/delis/etc. Monica’s makes a mean sandwich and Bova’s Bakery has exceptional desserts/snacks 24/7. Mamma Maria/Ciao Roma have a nice courtyard this time of year for a beautiful outdoor dinner, if you can get a reservation. The aquarium is also nearby if you’re into that 
If you’re near Cambridge/Somerville and are interested, some of the more famous universities have reopened for tours and for you to walk around. MIT and Harvard both have some nice museums, depending on what you’re into. I’m sure the others do too. There are also good restaurants/bars in the area
The seaport area has a bunch of breweries! Harpoon’s main(?) brewery is at the end of the strip which makes a good start/end of a walk
The Esplanade, Boston common, and public garden, are nice beautiful parks to walk through or catch a break in
If you’re a history buff, there are many tours available, but you can also just walk along the freedom trail at your own pace! It stops at several landmarks and can eat up a couple hours of your day
There are also other probably more common things like baseball/basketball/hockey stadiums, a casino, broadway type theaters, museums
What are some of your interests? Things you like to eat/drink? I’m happy to provide recommendations. There’s quite a bit to see and do in Cambridge/Somerville as well!
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I’m a musician in my spare time! played piano for over 20 years now and ive been really spending most of my music time learning guitar the last 1.5 years. anything music related and i’m interested.
i’ll probably see the classic historical sites if I am in the area too. staying at a hotel on Stuart street so anything nearby that /within a couple miles walking would be my primary interest. also i might get a weekend pass for the train system to head up to salem/providence too.
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Hmm… I’m unsure about music recommendations as I don’t play any instruments and I don’t know of quality music shops. You might see if some of the historic venues offer tours (e.g. symphony hall) or see if there’s some live music of interest. Dead and Company are playing Fenway while you’re here! Really, there’s quite a bit of live music if that’s your thing. You could check out some of the smaller venues like Cafe 939 at Berklee or Club Passim in Harvard Sq, for example, to see if there’s anything of interest.
Being on Stuart Street you’re pretty centrally located for most touristy stuff. You’ll walk the Common, go to Faneuil Hall, State House, walk Newbury St, etc.
You can always explore some neighborhoods like the North End (Pizzeria Regina is the most obvious recommendation and also my favorite!), Fort Point (pastries at Flour Bakery or a cocktail at Drink), or a short walk into China Town (Dumpling Cafe is my favorite spot).
I encourage you to take the redline north into Cambridge, too! Hope you have a good trip. Feel free to shoot me a PM if I can be helpful.
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Thanks will do!