Here's a list of restaurants I've eaten at as recently as last week and over the last couple years.
LEEWARD, one of the more interesting wine lists in Portland. Food didn't quite live up to the hype for me but I would definitely return.
CHAVAL, consistently very good. Basque, Spanish, French influences. Not a great wine list but there will be something of interest. All colors of Lopez Heredia were on the list last week. A Francois Cazin Petit Chambord was excellent with dinner.
IZAKAYA MINATO, Food is excellent. Drink sake and cocktails here.
TWELVE, new and getting a lot of attention. Food is exceptional. Wine list is terrible. I hear that may change but I don't know when.
CONG TU BOT, delicious Vietnamese. Drink beer here. Quirky,small but very fun atmosphere.
SCALES, Beautiful space on the docks of the Casco Bay. Terrific bar. Food is predictable New England fare executed very well. Wine list is hit or miss. Mostly misses.
FORE STREET, One of the old guards. Lovely space. Food is solid. Wine list has gotten much better over the years.
HUGO'S, I think the only place offering contemporary preparations. Haven't been in years.
CENTRAL PROVISIONS, Food here is really good. Some creative small plates that you can build a nice meal around. Wine list tends to vary from meh to having a few interesting things on it. Very popular. reservations are essential.
MIYAKE, One of my favorites. I always get the omakase with sake pairings.Wine list is disappointing.
HELM, I haven't been but the wine list looks like it may. be the best in the city. Mostly an oyster bar with a few entrees offered.
THE SHOP, go here for oysters. $1.50 a shuck is best price in city. Nice outdoor deck to relax on and slurp oysters mostly from New England.
HONEY PAW, I like this place a lot for lunch. Never had dinner there. Will be packed at lunch in the summer though.
EVENTIDE, gets lots of media attention. always a line to get in. expensive. not worth it in my opinion. go to THE SHOP to eat oysters.
DUCK FAT, people love this place. The French fries done in duck fat are exceptional. the rest of the menu is forgettable for me.
PAPI, a new Puerto Rican themed bar. Exceptional cocktails and atmosphere. I didn't eat here but the menu and dishes I saw coming out looked delicious. If I lived in Portland I'd go here all the time.
BEER- Maine is awash in good breweries. I am not a huge fan of IPAs which every brewery has in spades but a lot are now making very good lager, pilsners and stouts. Here's a list of worthy places to check out.
OXBOW, RISING TIDE, GOOD FIRE, BELL FLOWER (mostly too hoppy for me but theres some decent pale ales), LIQUID RIOT. Just outside of Portland in Freeport, MAINE BEER CO and MAST LANDING are worth a look.
Random Places to check out. Portland Museum of Art, Casco Bay Artsians (small but very interesting art gallery) Rosemont grocery stores. The bakery alluded to upthread below FORE STREET restaurant is STANDARD BAKING and it is excellent. Don't miss the EASTERN PROMENADE. Gorgeous views of the Casco Bay. There will be Food trucks there pretty much every day. Look for MR TUNA for delicious hand rolls.
Another fun thing to do is go to the docks and buy lobster and have the store steam them for you. HARBOR FISH MARKET AND FREE RANGE LOBSTER are best for this.
If you can take a side trip to Biddeford (20 minutes or so south of Portland) stop into Rabelais book shop. This place is a treasure. A large collection of first edition, out of print and rare cook books. The owner is incredibly knowledgable and very friendly. Best to email and see if he is going to be open when you are thinking of visiting. DM me if you want me to reach out to him as he's become a friend over the years.
I'm sure I'm forgetting some places but this should update the thread.