Sorted by location-ish. I tried to reduce the list to places I think are good for visitors vs. my absolute favorites, but I put a section at the bottom for places that may not be for everyone.
580 SW 12th Ave
My order: Grilled mackerel breakfast with a bloody mary. Their Dalgona coffee is quite good too.
Vibe: Fancy and modern without feeling stuffy. Comfortable but maybe not where you'd hang out for hours.
717 NW 16th Ave
Local bar with a small but super affordable breakfast menu. More a place for a drinking crowd than a fancy brunch crowd, but I come here all the time.
My order: Chicken fried steak or the two egg breakfast, and a classic 7AM Rainier.
Vibe: Windowless watering hole where you can comfortably drink for 20 out of the 24 hours of the day (and some do).
2390 NW Quimby St
Famous diner featured on travel food shows for their "mancakes" (huge pancakes, not cakes made of men). Expect a wait.
My order: Chicken fried steak with a coffee.
Vibe: Old school diner with plenty of kitsch to keep you entertained.
1101 SE Division St
Classic breakfast with a famous bloody mary. Expect a wait on the weekend.
My order: Eggs benedict with a Genie's bloody mary.
Vibe: Tightly packed, brightly colored diner with fast service.
2508 SE Clinton St. or 3765 N Mississippi Ave
Scandinavian breakfast at what is now a Portland classic. I grew up eating this kind of food so really like coming here.
My order: Æbleskivers and pytt i panna (hash) with smoked trout, and a mimosa.
Vibe: I've only been to the SE location, but it's a crowded and cute indoor space where you should expect to sit close to strangers. Not good for big groups.
There's really too many to list for lunch. These are my favorites but you'll find something good near you I'm sure. Vibe not included since you might get takeout/delivery.
Also, there are a ton of food cart pods that are probably the best place to go with a large group for lunch. Look up the nearest one to you and it's probably good, but I like the Mississippi Marketplace and Hawthorne Asylum.
338 NW 21st Ave
French bakery in my neighborhood with great sandwiches, pastries and bread.
My order: Roast beef or tuna fish salad. The tuna fish comes on a croissant and is the best I've had, I think.
413 NW 21st Ave or 1305 NW 23rd Ave for bigger location
Great Burmese food in NW - started as a ghost kitchen in the pandemic and now has multiple locations, so something must be right.
My order: Mohinga (fish chowder) with a side of samosas, or paratha dip
307 NW 10th Ave or 1126 SE Division St
Really good sandwiches known for their dutch crust (tiger bread)
My order: Borgata or The Godfather on dutch crust.
4138 SE Woodstock Blvd
German butcher / deli with outside seating, with a grill outside serving their sausages.
My order: All of the grilled sausages I can handle, and potato salad from the deli. They have a sandwich counter too which I've heard is very good.
2128 SE Division St or 685 NW 21st Ave
Really, really good pizza. NY size but with a chewy burnt crust. My current fav in Portland.
My order: Grandma slice
3808 North Williams Avenue
A Thai + American BBQ fusion restaurant. Dishes are pretty rich but are still good for lunch.
My order: White curry with brisket burnt ends.
4233 N Mississippi Ave
The best BBQ in Portland, located in a food cart in the Prost patio. This place is very busy, come right when they open.
My order: One of their big plates (to share) with ribs, sausage, and brisket. Sides are all good.
This is pretty subjective too, but these are places I would take people.
580 SW 12th Ave
Fantastic Korean restaurant run by the folks at Han Oak.
My order: Dinner menu seems more rotate-y so you'll have to check it out before you go. :-)
Vibe: Fancy and modern without feeling stuffy.
1818 NW 23rd Pl
Really great Thai place that is the "casual" wing of a famous tasting menu resteraunt (Langbaan).
My order: Curry, oysters, shaved ice.
Vibe: A millenial living room look book, busy and a little cramped but still relaxing.
960 SE 11th Ave
The Russian food and infused vodka keeps me coming back here, especially with groups. Has a small market if you want to buy anything for home.
My order: Sturgeon shashlik, horseradish vodka, and caviar.
Vibe: Relaxing open space with 80s Russian decor and music.
738 E Burnside St / 734 E Burnside St
Classic french restaurant in Portland, Canard is next door and is more casual. On the pricier side of things so prepare to spend a bit on the tasting menu.
My order: Menu is rotating so hard to say, I actually used to go to Little Bird downtown which had a great burger but they've since closed.
Vibe: Unknown, but probably on the fancier side.
923 SE 7th Ave
Japanese drinking food, sushi, and cocktails in a modern setting.
My order: One of every appetizer, normally. Great skewers and ramen, and whiskey cocktails.
Vibe: A bit cold feeling at a table, but if there's 1-3 people you should try to sit at the bar. I've never felt rushed to leave, they expect orders to trickle in. Does not have the traditional "izakaya feel" but is still nice.
2239 SE 11th Ave
Detroit-style pizza inside a brewery, what's not to love?
My order: The "#4" and a beer.
Vibe: Casual and relaxed, probably good for large groups.
401 NE 28th Ave
The best german restaurant in Portland, I think. I've never had a bad dish here.
My order: Jägerschnitzel, Kartoffelpuffer, and a Hofbräu.
Vibe: Probably the most modern feeling german bar I've been to, but is very relaxing and good for groups if you have a reservation.
This is hard. Portland has really great bars so I'm just going to pick a couple that I like. We have great dive bars and live music venues you should check out regardless of ratings/reviews. Go somewhere close to you!
Easiest to just go to Eb & Bean (645 NW 21st Ave), then look for a sign/gate/alleyway leading your to Bar Diane on the south side of the building
Really great wine bar in my neighborhood with good cocktails and snacks. Actually a great dinner location, but the menu is pretty small so hard to recommend. Not great for large groups. They're known for their tinned fish appetizers.
4534 SE Belmont St
British pub featuring an extremely large beer list with many rare rotating taps. Extremely cozy. Check out Movie Madness down the street while you're here.
1000 SE 12th Ave
A bar with arguably the best patio in Portland. Feels like you're at an eclectic friend's house. Cash bar, very busy so grab an outdoor table ASAP.
Any cafe or park in Portland will be great, but here are some places I like to hang out in.
734 NW 23rd Ave B
Cozy place to grab a cup of tea and snuggle up with a good book, or have a small get together with friends.
239 NW Everett St
Chinese garden in the middle of the city with a nice tea house inside. You'll have to pay for admission and then pay for tea, but it's worth it. Unlike the Japanese Garden, this is usually much less busy and the tea house feels more relaxing.
Not doing a list because this is super subjective, but I think going to a park (ex: Forest Park for hiking, Laurelhurst Park for picnics, Japanese/Chinese garden for relaxing) or going to one of our local theatres (ex: Cinema 21, Hollywood Theatre) is a great choice. The biggest thing is to go to many different neighborhoods/streets - too many people judge the city just from where they are staying. In particular visit SE Division, SE Hawthorne, N Mississippi, NW 23rd, and NE Alberta.
All that said, if you like video games you objectively have to go to Ground Kontrol.
These might not be for everyone, but are where I go when I'm in the neighborhood.
223 SW Yamhill St
The ultimate Portland dive bar. Beyond the bathroom smells I actually think it's nice to chill there and have a few PBRs, which are like $2.50 on draft.
2430 SE Division St
Nice dive-ish bar with really good fried chicken in SE. I used to live across the street.
426 SW Washington St
Third oldest bar in Portland - really fun to hang out in, pretty good with groups. Live shows next door.
922 NW 21st Ave
Very small excellent bar by the Prost owners. A bit fancy but the food at least is well worth it.
Suggestions for vegan/vegetarian spots: https://docs.google.com/document/d/1xVjvY6cnMRHIIwEw-1-gmWnUW5RqkFYgvTkgF9kaeJI/edit
ALSO DrupalCon peeps please don't be suckered in by those pink doughnut boxes. Voodoo treats its employees terribly and they're overrated. Look up Blue Star, Sesame, Pip's, NOLA.