Down to 3-help us hounds
We have two nights in Portland at the end of this month and we have narrowed our search to these three places: Caiolas, Cinque Terre, and 555. Bring on the opinions, Portland 'hounds!
while not a portland hound, I did visit recently. I ate at 555 and it was absolutely wonderful, highly recommended.
Caiola's feels more like a neighborhood resto (in a good way, and food is top-notch). Also, it may take you into the West End area of Portland that you may not otherwise explore.
Loved both atmosphere and food at 555, heard wonderful things about Caiolas but have not tried, had disappointing dinner at Cinque Terre. Of the 3 you mention, I'd recommend 555 over Cinque Terre, can't comment on Caiolas. If you'd like to add another to your list, I'd recommend Brescas, it's tiny and difficult to get reservations, but well worth it if you can book it.