Rob Roberts works at UpTake and has lived in Boston all of his adult life. He helped start two companies focused on travel recommendations. I think these are the kind of credentials that make him the ideal local to give us a few insights into this renowned city. I like his suggestion of the perfect day starting at 11:00 a.m. with a big budget…

Give 5 adjectives that you would use to describe the “feel” of Boston and its residents.
Historical, frigid, scholarly, tough, geeky…

What is your favorite neighborhood in Boston?
That would have to be Harvard Square…shoot, that’s Cambridge. You can walk around through Harvard Yard, go window shopping at lots of little shops, hang out at a café…

Which cuisine do you think Boston does best? What is the runner-up?
Italian. The North End is filled with tiny little places with amazing food. Ooooo…runner-up, not sure. Probably some kind of new food that I don’t eat. I’m sure about the Italian though.
What is the best free thing to do?
To make up for botching the last question, I’ll answer this one twice. Walking around Boston Common is really fun and free. There are gardens, ducks, statues, etc. Also it’s really great to tool around Harvard Square and Faneuil Hall during the summer…there are great sidewalk entertainers everywhere. (You should tip them, so that’s not technically free. But just between us, I’m really cheap and often just listen for free.)

What is your favorite type of entertainment?
That’s tough. Is eating entertainment? OK I’ll have to say the theater. The Theater District in Boston is great.

Describe the best family friendly activity.
Really depends on the time of year. The Museum of Science is a safe bet year-round…they have lots of cool interactive exhibits. But then there’s Fenway and the Red Sox during baseball season.

What spot would you send a couple, looking for a romantic weekend?
I think a nice hotel on either the harbor or the Charles River. Maybe a romantic walk along the Charles when the flowers are out in the spring (we really flip out here when we see green in the spring…it’s easy to forget how nice it can be outside when you’re buried under a foot of snow). Oh, and a harbor cruise. Or ditch Boston and go to the Cape.

Describe a perfect day…one that captures what your area/city is all about. In 3 sentences or less.
Alright…the perfect day. Does a budget come with this? My perfect day would have a big budget. How about a nice walk around Harvard Square in the late morning (no perfect day starts before 11am), then lunch in a café in Harvard. A quick T ride over to Faneuil Hall for window-shopping (or buying depending on the aforementioned budget), then walk over to the Theater District to catch some great performance. And what would make it really perfect is if the parking was free instead of $40.

Tell us about a place that you love to go, whether it is in the guidebooks or not.
OK here’s a secret place. It’s about an hour outside the city. It’s a small, family run water/picnic park on a lake. They have a huge lawn, a lake beach, and 3 awesome water slides. You can bring your own grill, your own food, and your own booze. It costs about $15 to get in. That’s it. No I’m not telling you the name of it…then everyone would go and it would be jam-packed!

What should we have asked, but didn’t?
Tips for going to Fenway Park and Museum of Science: leave extra time, they’re hard to find.
I have lived in Boston over 20 years, and still get lost around Boston. There’s one point on the highway where you swear you’re going the right direction and the Museum of Science is right in front of you and then…swoosh…it’s gone and you have no idea which direction you’re going. Secret parking is REAL hard to find in Boston. There’s a short strip of West Newton street in the Back Bay where you can park for free on weeknights…but you have to get there between 5:50 and 6:00 to get a spot. Before 5:50 you can get a ticket because there’s no parking before 6…after 6 it’s all full.