Portland, Oregon is the top place I’ve traveled to in the USA. From the trendy coffee shops, to the scenic waterfalls and wine country – this city has it all! I love to travel more than anything in the world, but never have I ever loved a city so much that made me second guess my home in Las Vegas.. until I visited Portland.
I went in the fall when all the leaves were falling, which made this city even more of a dream!
If you’re looking for the perfect, 3 day Portland Itinerary that will give a good mix of all this city has to offer, you’ve come to the right place! This detailed guide includes best things to do in downtown Portland, day trips from Portland, wine tasting in Wilamette Valley, Waterfalls worth seeing, where to eat so SO much more!
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Portland Itinerary Overview
- Day 1: Arrive in Portland, site seeing, and a professional spots game!
- Day 2: Willamette Valley Wine Tasting
- Day 3: Waterfall tour to see the outskirts of Portland
Where to stay in Portland?
Portland has a bustling downtown area that doesn’t feel like a typical big city. There are not hundreds of people walking the streets, minimal traffic and prices are fair! If this is your first time in Portland, I would highly recommend making the downtown area your hub. You are in the center of all the best nightlife, trendy coffee shops, best restaurants, and a short drive away from beautiful waterfalls or wine country. Click here to view hotels in the downtown area.
My second recommendation would be to stay in the Nob Hill district. It is less touristy with a lot of vintage shopping and wine bars. You may be farther from the famous sites, but the area is really unique. Click here to view hotels in the Nob Hill District.
What to Pack for Portland in the Fall
Other than my 10 travel essentials I can’t live without, these are my top 3 recommendations for a trip to Portland:
1. Travel size umbrella
It’s no secret that it rains a lot in Portland! It is green for a reason! I bring a travel size umbrella on ALL my trips because it’s so small and fits in my over-the-shoulder purse if I need it. I got mine on amazon for extremely inexpensive and comes in a ton of different colors. Click here for the umbrella I bought!
2. Light Rain coat
It rains almost year round in Portland, so regardless of the season you travel in, I would bring a light rain coat/wind breaker with you that you can easily throw over whatever outfit you’re in. I live in the desert where it NEVER rains, so I bought the least expensive one I could find. Click here for the rain coat I bought!
3. Rain boots
Rain boots are something I didn’t bring but regretted I didn’t. There is a lot of walking in any big city, especially if you are staying in the downtown area. You will want shoes that are waterproof and dry quickly. Click here for an affordable pair of rain boots!
3 Day Portland Itinerary
Day 1: Explore Downtown Portland
Again, I recommend staying in downtown Portland because it will make you walking distance to pretty much anywhere! We checked into the hotel and grabbed a quick bite to eat at this adorable restaurant: Bottle + Kitchen. This place has a wonderful cocktail menu and is the perfect place to warm up before exploring the city.
After your belly is full of yummy lunch and craft cocktails, its time to explore downtown Portland! The entire area of Portland is fairly small and easily walkable (unless it’s pouring rain, which is extremely likely ha!). If you don’t want to walk, there is an abundance of Uber/Lyft to help you get around!
Stop #1: Voodoo Donuts
First stop, of course, is Voodoo Donuts! This famous donut shop has boomed on social media, known for their crazy combination of donuts. There are now locations all over the USA, but this quirky donut shop started in downtown Portland. The amount of crazy combinations this place has keeps the locals and tourists coming back for more!
Stop #2: Powell’s City of Books
Next up, head over to Powell’s Bookstore, located less than a ten minute walk from Voodoo donuts. This three-story bookstore is the perfect place to pick up some souvenirs for back home! So many locals come here, grab a book and spend the day in the coffee shop that’s inside.
Stop #4: Keep Portland Weird Sign
The unofficial motto of Portland is, “Keep Portland Weird.” You can find this large mural painted on 3rd Street between Burnside and Ankeny. Probably on purpose, it’s located in a weird location near some dumpsters in an alleyway.
Most days you will find crowds of people near this mural to get their “Insta-worthy” shot! It is also extremely close to Voodoo Donuts!
Stop #5: Eat lunch at one of the unique food trucks
A popular thing to do in Portland is getting lunch at one of the many food trucks! They have every type of food you can imagine, so just pick whichever one has the longest line (that means the food is good!) and continue exploring!
Stop #6: Nob Hill District
Next stop, the Nob Hill district. This was my favorite part of Portland by far! To get there, you will walk through beautiful neighborhoods that are filled with colorful, Victorian-style homes. Nob Hill is filled with wine bars, vintage shops and stylish bistros.
If you are doing this Portland itinerary on foot, the walk from Downtown Portland to the Nob Hill District will be about 30 minutes. I know that sounds long, but there will be so many shops and coffee shops along the way to rest your feet at!
Stop #7: Portland Trail Blazers Game
Last stop of the very busy day (hey, you only have three days, you have to make the most of it!) is catching a Portland Trail Blazers basketball game. It was a good break from the cold, rainy weather and was a lot of fun to see! You can check out their game schedule here.
Day 2: Wine Tasting in Willamette Valley
I have been wine tasting to beautiful areas (Champagne Region of France, Napa Valley, Paso Robles, and Temecula to name a few) and I can honestly say Willamette was up their with the big names! Everything is very spread out, green and has expansive views! The only downside to Willamette is they do not have a variety of wines to taste, since this region specializes in Pinot Nior.
The drive to Willamette Valley is about an hour, making it the perfect day trip from Portland! I wouldn’t recommend driving because on this itinerary, you will get pretty tipsy!
You can hire a driver who picks you up in Portland and can recommend some of the lesser-known wineries. I would highly recommend the company we used: Insiders Wine Tours. We had the owner, John, who was simply amazing but we were his last ride before retirement. His kids took on the family business and if they were anything like John, I am sure you will receive the same great experience.
Some other Wilamette Valley tour options are through Viator or Get your Guide. I’ve used both of these sites on numerous occasions and can personally vet for them!
Stop 1: Arborbrook Vineyards
Arborbrook is a family owned vineyard that specializes in Pinot Noir. This was my favorite winery because we got to meet the owner, Dave, who is a banker by weekday and winemaker by weekend! He filled our glasses while sharing his passion for wine. You can stroll through the vineyards just outside the tasting room, which makes for the perfect photo opp!
Don’t forget to say hi to the winery dog that roams the property! He was just a puppy when I visited, but I am sure he is all grown up now 🙂
Stop 2: Aramenta Vineyards
Aramenta Vineyards is a quaint mom & pop winery! We were seriously the only people there – such a hidden gem! The property is beautiful and the wine was delicious, couldn’t ask for anything more.
When we arrived at the property, we were welcomed by the wine makers into their home to taste some of their finest wine. They showed us the wine making process that happens right in their garage and gave us some cheese and crackers to snack on.
Stop 3: Fairsing Vineyards
Fairsing vineyards is a much larger winery. It was very crowded, for good reason – the view was second to none!
They have a large tasting room with comfy couches, fire pits, and an outside deck. If you go out towards the edge of their property, they have lawn chairs that face the outstanding views of Willamette valley. We went on a gloomy day, so there were plenty of seats open, but I would imagine all of these would be taken on a sunny day!
TIP: I would skip the tasting and just grab a glass of wine. Sit out on the lawn chairs and soak in that view for as long as possible!
Stop 4: De Ponte Cellars
De Ponte is another winery with a great view! They have a patio out back that overlooks the valley. From what I recall, the wine was good but after a few hours of tastings, it all begins to “blend” together (ha, get it?).
Since I went in the fall months, the vines were pretty bare. If you travel to Portland in the spring or summer, these views will be 10x prettier!
Day 3: Oregon Waterfall Tour & Flight home
If you take a late flight out, it will give you plenty of time to do a waterfall tour in the morning! These tours only last a few hours and will pick you up from your hotel in downtown Portland.
Unfortunately, I went the same year there was a major forest fire so a lot of waterfalls were closed due to mudslides. I am already dying to go back in the summer and spend a full weekend exploring the nature side of Oregon!
There are endless tours to choose from that pick you up in downtown Portland, I would recommend picking one that includes the Columbia River Gorge and Multnomah Falls (the two most popular sights). You can browse pricing and available tours here!
Until next time, Portland!
Like I’ve said before, Portland is one of my favorite cities in the USA and a city I will probably go back to time and time again. If you have the chance to visit Portland in the summer, I would recommend spending a few days hiking the outskirts or making a day trip to the coast.
In the Pacific coast area? I think you would love these guides:
- 3 Day Weekend in Seattle
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- Big Sur Road Trip
- Quick Guide to visiting Monterey, CA
Like wine tasting? I think you would love these guides:
- Wine tasting in Napa Valley, California
- Wine tasting in Temecula, California
- Wine tasting in Paso Robles, California
- Champagne tasting in Champagne, France
Thanks so much for stopping by! 🙂
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