I have never been to Portland, but we did the Seattle/San Juan Islands thing a couple of years ago. All I can say is that it was a very long day getting to Friday Harbor from the east coast. Non-stop to Seattle, 2 hour van ride to Anacortes to catch the ferry, then a long (2 hrs.?) ferry to Friday Harbor. We brough our bikes with the couplers, so we each had 2 suitcases, big ones, one with bike inside (regular airline regulation size) and one full of 2 weeks of regular/cycling/hiking clothing. Getting the bags up the ferry plank and through the terminal was hard. On the way back to Seattle, people were giving me dirty looks as I was struggling with the load, like I was some kind of rich b*, who needed a lot of clothes. Finally, I looked at one guy and said, " What? It's a bike in there," in my most obnoxious Bostonian way, and their attitude changed. We had friends pick us up in Friday Harbor, though, which was good. On the way back, we spent 3 days in Seattle, so it didn't feel so stressful, before flying home.
ETA: While getting there was stressful, we loved the San Juans. I loved Seattle, too, and even got to have lunch with 2 TEers while there. We spent an afternoon/night in Seattle, also last winter, on the way to and from the Methow valley.



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….and of course in portland there is salt and straw ice cream on nw 23rd. The Saturday market in waterfront park is a great place to wander though too. Some great craft breweries if you like beer. Some great contemporay art galleries including the oregon center for photographic arts (blue sky gallery). Portland is one of my favorite cities and home to my best friend from college who always takes me to the most interesting places....and caused me to do and have a great time on the seattle to portland bike ride.
You do not need a car to see the city at all but if you'd like to get out and do some day trips/hikes, it's helpful. There is always zip car or Uber, of course. And then there's us...so if we aren't working, we'd love to take you places!