I just returned to Boston after a week at a trade convention in Portland and I have to say that you Portlandites sure have some fine restaurants to chose from. I was staying at the Heathman Hotel so it made exploring restaurants in the city very easy. During the week I had the opportunity to try the following places:
Blue Hour: Very nice place, great service and good food carefully prepared and presented.
Nuestra Cocina: Boston is not the city to look for good Mexican food so I was very pleased when friends suggested this place. Small informal place but really good Mexican. We had some excellent tamales with a tomatiilo sauce and a pork with adobo that was outstanding.
Jakes: I understand that is place is somewhat of a Portland institution sort of like Durgin Park here in Boston. I enjoyed sampling many of the local oysters many of which we don't see in Boston. I had the broiled Sturgeon which is another fish we rarely see back here and it was delicious.
Piazza Italia: The North End of Boston has over a hundred Italian restaurants that cover a wide range of price points and quality but I would rank this place right up there with some of the best we have back here. Excellent pastas, homemade sausage and very traditional recipes made for a nice evening.
Hiroshi: I think this was my favorite place. We have some great Japanese places in Boston but few of them are as a good as this place was. I lived in Japan for almost 7 years and have a problem finding truly authentic Japanese food in the US. Hiroshi is truly authentic Japanese. The manager informed me that because Matsutaki mushrooms (Pine mushrooms in English) were in season they were featuring them in several of their dishes. I took advantage of this and had a them in an excellent Chawanmushi, a Dobinmushi and a serving of very simply grilled Matsutaki with a Ponzu dipping sauce. We also sampled quite a bit of their sushi offerings and found them all to be first rate. People in Portland are fortunate to have such a great Japanese place and if I lived there I would be at Hiroshi at least once a week.
Lastly, You should be very proud of your trolley system. The fact that it seems to run reliably, is free within the city center and the cars are clean and comfortable is something any city should be proud of. The MTA in Boston pales by comparison.