I like the Southeast of Portland the best. I’d start off going to the Waffle Window. There’s a Blue Star Donuts right across the street, and then KURE Juice Bar with great acai bowls is also in the neighborhood. So there are lots of good breakfast choices!
I’d get coffee around there. My favorite is Good Coffee on Division, or Heart on Burnside. They just opened up an Upper Left Roasters too, and they’re good.
Then I’d probably just walk around on either Division or Hawthorne. You could easily just get lost in the little shops there. Eventually, both streets hit the Eastbank Esplanade, a bike path along the Willamette. I’d just read a book, walk along the river, look at the skyline.
And then I love the food carts here. My favorite is on Division and 28th—awesome, the best. There’s a double decker bus there with a vintage dress shop.
Then I would go get ice cream from Salt and Straw, the honey lavender ice cream.
There are also a lot of bars in that area. The Richmond Bar is pretty chill, with a back patio that has fires, so it feels like you’re in a log cabin. Or Circa 33, on Belmont just one north of Hawthorne.