Road Trip Plans: Portland!

My family has taken a liking to “all american family road trips”, and I’ve planned every single one of the trips we’ve taken. From the Grand Canyon to Yellowstone, I’ve had my fair share of intense googling and hotel booking. This summer my parents want to go to Portland and Seattle, and I think it’ll be interesting to see how much of my plans actually go through! So here’s a peek at my itinerary I’ve built up for our Portland part of the trip! (Seattle will be a separate post!)

Background on Our Road Trips:

I have a very sight-seeing oriented family. Sight seeing is EVERYTHING to us. While other families might enjoy more physical activities such as kayaking, or going to amusement parks, looking at pretty views is our idea of “adventuring”. Honestly, simply driving by the coast is enough to entertain us.

So with that being said, when I plan my trips, I go extremely budget friendly. Why pay 15$ each to look at stuff when we’re already satisfied with looking at stuff outside for free?

My inner scrooge also comes out when booking hotels. There were times where my idea of budget friendly has pushed my dad’s limit (which is pretty low already). So this time around I’ll make sure to book a place where my dad doesn’t have any sudden urges to go out and check if our car has been robbed.

My family’s attitudes about how we spend our time are very…mixed. We love stopping by random places and breathing in the view, but we’re also a very “let’s hit as many spots as we can in our small time gap” kind of family.

Last year, I googled what’s a good time frame for visiting Yellowstone National Park, and people have said at least one week.

Well in one week my family already looked around Salt Lake City, snooped around Idaho, took majestic pictures of Yellowstone, stared at Montana’s beautiful trees, and made it up to Saskatoon Canada.

So yeah, we’re definitely not the type to stay in one place for very long.

We have about 5/6 days for our Portland/Seattle trip, and I’ve had a blast looking up places.

So if you’re planning on going up to Oregon & Washington, here’s my Road Trip plan you can build on as well!


DAY 1 (Option 1): Drive up and escape California

My day one plans are fairly simply. Make it out of California, or at least as far up North as we can possibly go.

So DAY 1 is all business. No sightseeing since we just want to make it up to Oregon.

I’m guessing we could probably make it up to Redding, but if we really pedal to the metal, we can cross the border into Oregon in one day.

DAY 1 (Option 2): Drive up and stop by Yosemite, then stop at Redding

So as you can already see, my family has no problems with keeping our options open, so as a planner I have to prepare for all possibilities.

My dad has the final say when it comes to our plans, and he’s mentioned that he wants to stop by Yosemite before heading up to Oregon. This is fine, but only if we leave on Saturday since we want to see the Eclipse in Salem, OR on Monday.

So that’s a good two days to drive up which is plenty.

BUT if we leave Sunday, it’s a default option  1. NO WAY we can make it up to Salem by Monday morning if we leave early Sunday. NOPE. We live south of LA so it’s a good 13/14 hour drive straight from our place to Salem.

DAY 2-3: Oregon, Oregon, Oregon! Portland here we come!

Day 2’s plans already have me drooling. Day 2 with however our plans go the first day, will be spent driving through Oregon. I am psyched!

My family tends to take random stops, and I’m hoping we find some cool places to stop on the way!

Once we possibly take in the glory that is the Eclipse, it’s all Portland from here! Oh man I can’t wait to go to Portland. It’s gonna be one of our main stops.


1. Multnomah FallsRelated image

This place looks beautiful online! It’s one large cascading waterfall (I’ve never seen a waterfall!), and the great news is you don’t need to do a strenuous hike to get there which is important since my parents have foot/knee problems.

Funny thing is, while I was googling it, I think I found that it has a gift shop and that part also got me pretty excited. I love gift shops.

2. Vista House

On the drive back from Multnomah to Portland, we’ll pass by the Vista House.

Image result for vista house oregon

It’s a cute little place with a breathtaking view. I don’t think we would stop here for long, just to take a couple pictures and look inside the small museum which has free admission!

It looks really interesting, and since we’re passing by, why not?

3. The Grotto (finally in Portland!)

8840 NE Skidmore St, Portland, OR 97220

This is a Catholic outdoor shrine that we’ll pass by right on the edge of Portland. My family is Catholic, and I think this visit would mean a lot to my mother, so I definitely put this on the list. Even if you’re not religious, I think it’s might be a beautiful place to stop by if you have the time. It’s free for the most part, except for one part where you have to pay admission to go up to the upper levels. Image result for the grotto oregon

There’s also a church I think, not completely sure but it would be great if we arrive and there’s a mass going on. My mom would go crazy for that place.

The pictures make the place look so beautiful!

4. Tom McCall Waterfront Park

This park is a nice green space with two Portland bridges in view. People say it’s a great place to walk around, but it can also be sketchy since there are a lot of homeless people, and to my horror “needles” lying around.

While my family has come across the homeless population (San Francisco & Sacramento anyone?), I don’t think we’ll feel great if we see needles on the ground.

This is definitely a “maybe” stop, but it might be a nice place to take pictures of the Bridges!

5. International Rose Gardens

Image result for international rose gardensThe international rose test garden is “a rose garden in Washington Park in Portland, Oregon, United States. There are over 7,000 rose plants of approximately 550 varieties”.

I’m  not sure if there will still be roses by the time we get to Portland since it’ll be near September, but I hope there will be!

This place sounds amazing, and I don’t think it’ll hurt to try and see if there are any left! My cousin visited this place in June and her pictures were gorgeous!

6. Pioneer Courthouse Square

Image result for pioneer courthouse square

Pioneer courthouse square is considered the “living room of Portland”. I think this would be a great place to start going through the city parts of Portland after going through waterfalls, gardens, and parks. There are several stores around pioneer square, and if we drive up north we can hit the Pearl District!

7. Pearl District (Powell’s Bookstore & Voodoo Donuts!!)Image result for voodoo donuts

The Pearl District sounds like a place that’s meant for a chill three day exploration rather than a quick 30 minutes look-see.

To be completely honest, I don’t really know what the Pearl District is about. It sounds like place that would be fun to casually walk around with friends rather than family, but it wouldn’t hurt to stop by if there’s time.

I do want to stop by Powell’s Bookstore and Voodoo Donuts! Especially voodoo donuts, because I remember watching the food network when I was younger and being incredibly fascinated by the chocolate voodoo doll donut while whispering “I wanna go there!”.


  • St. John’s Bridge
    • A really really cool gothic bridge in the northern part of Portland!
  • Forrest Park
    • If we need more nature in our life!
  • World’s Smallest Park (Mill’s End Parks)
    • Just a funny little thing to stop by if we have time!


Overall, I’m so excited to visit Portland! It’s a place I always always hear about but I don’t have a clear picture as to what exactly is so great about Portland. After googling, I feel so excited!

The pictures don’t capture a cities vibe, so I’m really excited to feel it in person.


Anyone else going or went on a cool road trip recently? I’d love to hear some stories! Or maybe some tips about visiting Portland!

-Kae 🙂









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