touristy to-dos:

multnomah falls. it's a drive, a car is necessary. the earlier you go, the better. stop by other water falls and vista point on the way there or back to get the most out of the gorge. plan on being out of the city for half a day!

the destination for portland souvenirs. i always tells visitors to pick a random thing. if they have less than 5 books on it, you win! good job, weirdo. (note: if you've been to/frequent strand in ny, you can skip this one)

cathedral park. beautiful in the sun. stunning in the rain. get some coffee and chill. two stroke is cool and a convenient walk.

hawthorne asylum. once upon a time portland was unique for its food cart pods. if you want the experience, this one is ol' reliable. fret not, midwesterners, there's tons of weather-proof seating.

quarterworld. we basically live here. pinball, giant space invaders, obscure vintage games, sipping beer while being serenaded by a tesla coil. remember the experience forever with a pair of undies. i did.

eem. you simply must. no reservations but it's worth the wait. trust.

international rose test garden. a massive garden with great views of downtown and mt. hood. best of all: it's free.99.

movie madness. it's a pilgrimage. rent the miniplex if you want, it's your trip, i don't make the rules.

giftykitty. love cats? you are so welcome. don't love cats? try again, friend. allergic to cats? great news. for some reason they don't have a shop cat.

omsi. great for kiddos and for kiddos at heart. check out omsi after dark for adult-oriented activities.

canard. what do you pair with your wine? if you said foie gras dumplings, you're in luck. if you said fried chicken wings, you're also in luck.

horse brass. 2 blocks from movie madness, this is an english pub that honestly feels like a hug.
touristy to-don’ts:

we don't stan union busters. especially for mediocre donuts you can also get in denver, nola, tempe, and now, chicago. try pip's or heavenly donuts if you've got a craving!

pioneer square. if you really wanna see the sign, google will suffice. unless there's an event or band playing, this area is kind of a big tri-met stop.

going out of your way for a photo op in front of the stag sign is not worth it. there's not much to do in the immediate vicinity, and there are plenty of other great views near the waterfront. i assure you, you will see the sign while you're here.

river cruises and ferries are expensive and time consuming. there are faster (and warmer) ways to see what you want to see.

is the grotto nice? yes. is it also pretty expensive for what it is? yes. does it have the best views? you already saw the airport.

this is the spiciest take. if you love japanese gardens/koi ponds in general, by all means. is it beautiful? yes. but it's pricey and time consuming. if you're down, commit.

recommended
is portland safe?
despite what conservative outlets may tell you, portland is not a post-apocalyptic hell hole with zombies chasing down residents. people raise their families here and, believe it or not, like it.
we do! portland is also a small, very residential city that feels more deeply the effects of issues plaguing the whole country including lack of affordable housing, access to mental health resources, and vacant spaces exacerbated by the pandemic.
in a very literal sense, these problems are happening in our front yards, unlike larger cities that make it easier to turn a blind eye to other people’s suffering. the visibility of the homelessness crisis also does not mean that we are unsafe. crime everywhere is rising, we all have work to do. but portland doesn’t even make the top 25 most dangerous cities in the U.s., and doesn’t even make the top 50 according to many other sources.
you will certainly be able to enjoy a fun weekend taking in all of the cool things portland has to offer.
as with any city: practice caution, and show compassion.