Lisbon
My favorite place to stay in Lisbon is the Hotel Valverde, a quiet but central boutique hotel. Great wine selection, but let's be serious-- what place doesn't have amazing wine in Portugal?
There is so much good food in Lisbon, where do I start? The farm to table movement so fresh, and Feitoria really exemplifies this. I love seafood, so A Cevicheria is a great pick. If you're there during the summer, nights are sublime at The Food Temple. Remember that most restaurants on closed on Mondays.
I am obsessed with the Quinta da Regaleira, next to Sintra (which is a 20 min train ride from Lisbon) because it reminds me of Pan's Labyrinth.
Porto
Livaria Lello is the bookstore that the Harry Potter was based on, and even though it's annoying you have to pay an admission ticket to it.
Wine tour? Yes please! Ferreira is one the most famous and easiest to visit. Bring a jacket-- the cellars are chilly!
Faro