Hey all! I’m Sam Kieft, wife of Zach Kieft. When we first met I had never traveled, that was more of a Zach thing. So once we began to travel together, I began to help plan for those trips. Whenever it’s been awhile since we’ve traveled last I usually feel overwhelmed, stressed, and brain dead just trying to plan out the perfect trip. I know that those feelings can begin to make us want to just give up or make an excuse to try it for a different time. Luckily I have Zach with me to help push me forward and remind me that once we are actually on the trip, you’ll usually not be able to notice if it’s working out perfectly or not. So all that planning we do ahead of time is super important but it doesn’t have to be so overwhelming.
For those that are beginning to travel for the first time and just want to make sure they aren’t forgetting anything, or could use a helpful hand – I wanted to make a blog series to help you plan for everything you’ll need to have a perfect trip!
So let’s get to it – let’s plan this trip to Portland together!
The best thing to remember is all you really need at the end of the day is how to get there, how to get home, where are you sleeping at night, and how do you want to get from place to place? So once you have your flights, hotel, and rental car you’re pretty much 80% done!
1. Choose Your Dates
Best time of year to visit Portland I would say is either in April, July, or October.
April – Our rain is hit and miss in April. Some years it’ll rain everyday and other years it’ll be drier but you’ll see all our spring blossoms around the city and in neighborhoods. We have lots of wild roses and tulips that will pop up & it’s also the time of year when all of our trees have their leaves back so the views will be more beautiful.
July – Not much rain at all, also not fire season quite yet so you shouldn’t have to worry about smoke in the air.
October – Usually isn’t hardcore rain season just yet. It’s also the time of year that our leaves begin to change colors which looks epic as you drive into the city!
Sometimes this is easiest to do while booking your flight if you don’t have specific dates that you have to be there. Something that we take into consideration is the price of flights. Prior to doing a google search, open up a private browsing window – this stops companies from being able to save your search which can lead to them upping the price when you later search the same trip.
If you google “flights from BLANK to Portland” google will show you flight results that look like this:
Once you click on the departure date & it’ll show you prices per day:
This is how we usually pick our dates. It’s showing you the cheapest option you’ll have for the round trip. Sometimes that lowest price is for a lower company like Spirit or Frontier so prices will go up from there, but it can also show you cheaper date trends.
Google is also awesome because they’ll always have a price graph that tells you if the dates prices are normal or not for that time of year:
From all of this, you should be able to choose the dates that you want.
Pro tip: If you are wanting to visit downtown Portland, I’d recommend visiting during the week. Most locals don’t live downtown so the weekends can be pretty quiet and eerie. During the week you’ll be able to see locals walking to work, on break, and a more bustling night life.
2. Plane Tickets
Plane tickets are straightforward once you choose what company you want. What I’ll share from our experience is we usually fly with Delta or Southwest if we can help it. We used to fly with American or Spirit but began to have our share of delayed flights and felt that in the end, our time traveling should be filled with fun, rewarding experiences that are usually worth the extra $100 in flight prices for the better company.
For traveling you’ll need to decide if you want to bring luggage with you or not. Our advice is to not! You can save $30-80+ each way from not needing to check in a bag, which saves you money in the long run of vacations. We also just like the freedom of it. Sometimes traveling can send you down some interesting neighborhoods that you don’t know and the more luggage you have with you, the more you look like a tourist and a target to get robbed. We both will pack one backpack and make due with what can fit which is usually 3-4 days worth of outfits. From there, we know that will mean we’ll need to buy an outfit or two for the rest of the days or find a Laundromat.
3. Hotels
With Portland, you can either choose to stay in a hotel or Airbnb. Airbnb will usually be cheaper than hotels but hotels can usually get you closer to downtown if that is where you want to stay.
If you are wanting to stay downtown which is a good idea if you want to walk through the city, use the streetcar, feel like a local – these are some spots I’d recommend:
$ Modern Nob Hill Getaway – AirBnb
$100/night located in the alphabet district which is NW of downtown. Beautiful location filled with shops, restaurants, and busy dinner night rushes. Can easily take the streetcar or max to get into central downtown.
$$$ Hyatt House Portland Downtown
$227/night located right downtown at the beginning of SW Waterfront. Perfect location to stay in a safe, clean spot downtown and still have that hotel vibe.
If you want to see more of hipster, young, eclectic side, I’d recommend staying in SE near Hawthorne, or Division. These areas are beautiful neighborhoods lined up with beautiful cafes, restaurants, local shops, and small theaters. Here are two AirBnb’s close to Hawthorne Street:
$83/night. It’s a detached living space in their backyard and they’re a super host.
$$ Modern Hawthorne Guesthouse
$136/night. They’re a super host and you get the entire house.
4. Transportation
There are a couple of options for transportation – car, bus, max line, or streetcar. The bus, max, and streetcar all take the same ticket through Trimet. So if you purchase a 2.5 hour or day pass, that works for all 3 simultaneously. You can either download the app to purchase tickets or purchase them at pay stations near most max stops. If you’re staying downtown I’d recommend skipping the car and using transportation. Rent a car for a day or two when you know you will do excursions and not be at the hotel as much so you aren’t paying around the clock parking and not using it.
For driving, only things to consider is lots of areas near downtown is paid parking. It’s said that our city gives out the most parking violations than any other city in the US. We even got a citation when we first visited before moving here!
Some Tips:
-DOWNLOAD THE KITTY APP. It’s a life saver for paid parking. It allows you to put in the zone that you’re parking and you can add funds if needed.
-If a zone says 2 hour or 4 hour parking only, that is accurate. It will not allow you to add more money to your kitty app if you’ve already paid for that amount of time.
-parking is free after 7p till 7a throughout the city.
-there are some areas that are free to park but that will be in neighborhoods like SE, or alphabet district. All actual downtown locations from 1st street to 12th will be paid parking only.
-You’ll need to know how to parallel street park for most parking throughout Portland area.
-If you can’t parallel park you can find parking garages or parking lots to pay it’ll be a little more expensive though.
-If there is a sign that says “2 hr parking” that goes for the whole block until the next parking sign that says other.
-Watch out for yellow paint on the sidewalk (that means tow zone), and watch out for fire hydrants (always tow zone if you block it).
Street Parking in Downtown Portland 
Streetcar
Follow those and you’ll be golden!
5. COVID Protocols
As of July 2021, we are back to normal for the most part. I’d still recommend bringing a mask with you. We do have lots of local shops that will have signs saying they still require a mask and usually won’t have some to give out.
Only time you will be expected to wear a mask otherwise is in health care facilities and on public transportation.
For updated information, you can check out this website
6. What to Pack
I’d recommend packing a sweater or light jacket no matter what time of the year. Early mornings are always a bit nippy it seems, even in July.
Check your weather app prior to packing to know if you’ll need a rain jacket or not. You’ll notice that locals usually don’t use umbrellas or hoods but just walk in the rain. We’ll notice if you’re a tourist or not depending on what you use 😉
Our culture is more laid back, natural beauty style for sure. Most girls don’t wear make up. So no need for lots of fancy, flowy dresses. You’ll see most girls wearing either jeans or shorts with a cami or crop top.
Definitely comfortable walking shoes since we are a walking city.
If you’re going to the coast, bring layers. Even during July our coast is usually at 50/60 degrees for the high of the day and is usually windy.
7. What to Check Out
Definitely look into ways to check out the following:
-dinner somewhere on Hawthorne in SE
-dinner or lunch down Mississippi street in SE
-lunch or dinner down Division street in SE
-walk along the waterfront in downtown Portland. Best place to begin is at the corner or Jefferson and 1st and cross Naito Parkway to get to the grass area that goes along the Willamette River
-Get dinner in the alphabet district (should be between 21st and 24th street in NW Portland).
-Breakfast or dinner in Lake Oswego – or just grab ice cream one afternoon at Salt N Straw out there
-Get lunch or dinner in St. John’s
-Check out the newly developed SW Waterfront area. I’d recommend getting coffee and pastries at The Oracle and walk around that area.
Waterfront down walkway – can find behind Tulsa dealership in SW Waterfront 
Waterfront near Macadam and Pendleton Street
8. Safety
Portland is a very safe city. You can walk around anywhere, you don’t have to worry about someone trying to rob or jump you. What I do want to be transparent about is what you’ll see and witness downtown. We do have a large houseless community – most of them do seem to be drug addicts. What I would recommend is to stay away from Chinatown, and burnside street near 3rd-5th street. We have a food bank/shelter over there and they have a large community around it.
I hope this was helpful! I remember when we first visited and moved out here we didn’t really know what parts of the town we were actually checking out/a part of. So my list of what to look into will help you ensure you see all sides of Portland. & also check out my blog for what actual sights to see and do excursions to.
Pioneer Square at night 
View of downtown from OMSI 
Providence Park – Stadium for Thorns/Timbers
The Vagabun 