You’re making a great choice! Boston is a great city and a wonderful place to visit. Here’s some additional advice I typed up a few years ago for a friend.
We can be more helpful as you make decisions, as others have said.
A few restaurants I like:
Saltie Girl or Row 34. For seafood & oysters, this is where to go.
http://row34.com/
Myers + Chang. If you want spicy, funky Asian food, this is where to go.
http://www.myersandchang.com/
Alden & Harlow. Small plates. I love their vegetable dishes.
http://aldenharlow.com/
Near Fenway: Go to Timeout Market. An upscale food hall with stalls from around the city (Mediterranean, Italian, seafood, sushi, donuts, etc)
BREAKFAST/COFFEE:
- Tatte Bakery. Bunch of locations around the city, outstanding coffee, pastries and shakshuka. It’s become an East Coast chain.
http://tattebakery.com/
- Flour Bakery: Bunch of locations around the city, outstanding sandwiches, sticky buns, and cakes.
https://flourbakery.com/
Things to do (non-athletic)
The MFA and the Isabella Stewart Gardner Museum -- There’s always an interesting exhibit, and the Gardner museum is basically across the street.
Boston Public Market -- It's fun and a great place to buy local gifts for people (bowls, spices, etc.)
https://bostonpublicmarket.org/
JFK Library and Edward Kennedy Center -- They're both interesting -- especially if you’re a JFK fan this is a good spot. But for kiddos might be tough.
Re North End, the
original Regina Pizza (NOT the chain stores) is authentic, coal fired pizza:
https://www.yelp.com/biz/regina-pizza-boston-2)
Harvard Square -- Just walk around. Harvard Yard is beautiful, cafes, great bookstores (Harvard Bookstore), a legendary burger place (Mr. Barley's -- was on Diners Drive ins and Dives), some good shopping, can walk down to the Charles River and wander, etc.
Coolidge Corner in Brookline: I’d consider staying here if this weren’t your first time. It’s a lovely little neighborhood with a great independent bookstore filled with cool gifts (Brookline Booksmith) and lots of little shops, plus two great authentic Japanese markets, and Zaftigs is fun for brunch.
South End: Charming and picturesque neighborhood with shops, homes, restaurants, a great playground for the kids, etc.
NOTE: on weekends, SoWa Market in the South End is great. Food trucks, hundreds of independent vendors, etc.
With a car
Drive 25 mins to Concord -- See the Old North Bridge where Massachusetts invented America (and a beautiful little tribute to two fallen British soldiers who are buried there that the kids might find eerie: They came three thousand miles, and died, To keep the Past upon its throne // Unheard, beyond the ocean tide, Their English mother made her moan.), then go into town which is adorable. One of the best cheese shops anywhere, lots of furniture and dress shops, an old cemetery, cafes, etc.
Drive (or commuter rail) 45 mins-1 hour to Salem: Witch central. Salem itself is actually lovely, and in fall the lead colors and seaside charm are in full effect, as is the Halloween regalia and tourist trapping attempts (the Witch Museum is straight out of 1974 and feels it). Kids would like it i
Drive 1-1.5 hours to Cape Cod (Woods Hole/Falmouth) or for another 45 mins take a ferry to Martha’s Vineyard). It’s really wonderful, fried seafood, beaches, inns, soft serve ice cream, mini golf, etc.
Drive 2+ hours: Portland, Maine. Could catch a Sea Dogs game, have the best lobster rolls of your life, oysters, blueberry anything, donuts, great beers, and stunning seaside scenery (lighthouses, people who look like they work in lighthouses, etc.)
Edit. You also aren’t starting at zero. This site is about kid friendly visits to Boston with different interests in mind:
https://bostonmoms.com/visiting-boston-staycation-vacation-recommendations/?gad_source=1&gclid=CjwKCAiA29auBhBxEiwAnKcSqgdgLYiZDn9PJwulaPNDNfn-tWY31saZzG5vpRmLOD-k6bXIK9W1sxoCoW0QAvD_BwE
