Updated: Nov 22, 2019
This article by Wannabe Portlandy (http://www.wannabeportlandy.com), offers some great suggestions for showing your friends & family around our fabulous city of Portland.
Downtown Portland – Broadway
Every year, I get requests from friends and followers to create Portland itineraries for them. This is something that I enjoy doing and I go the extra mile of even making detailed presentations for friends. Each traveler is different and so I make it a point to tailor fit the itineraries that I make for each individual personality and preference.
I recently crafted a personalized 7-Day itinerary for three of my friends and three of their kids. I am sharing the itinerary here because it might help you plan your trip to Portland too.
But first, a little bit of perspective on why I made this itinerary the way it is. First of all, my friends are world-travelers. They have been around Asia, Europe, and North America. So I wanted to suggest places that are more unique to PDX. For instance, I intentionally did not suggest for them to eat in any Asian restaurants even if this is popular in Portland. Most of my foodie suggestions are focused on good American food. Secondly, my friends were traveling with kids that are 5-years old and below. So most of the places that I have suggested are kid-friendly and places that won't require waiting in line for more than an hour.
So here it goes!
Day 1 (SUNDAY) – Welcome to Portland!
10:30AM – I immediately had my friends go to Olympia Provisions for brunch. Don't forget to order the Steak Eggs Benedict here. Advanced reservations is a must!
2:00PM – After brunch, I had my friends take the Best of Portland Walking Tour. This is a great crash course on what makes Portland, Portland. This tour will take you around downtown Portland's key highlights for 2 hours. Advanced reservations is a must!
5:30PM – Screen Door is a PDX foodie hall-of-famer so go here for dinner and make sure to order the buttermilk fried chicken. Tip: Screendoor opens at 5:30PM for dinner. Try to arrive at least 15 minutes earlier or else you'll end up waiting in line for a much longer time.
Day 2 (MONDAY) – Foodie Day Part 1
9:00AM – Have breakfast at Tasty 'n Sons. Make sure to order the Potato Doughut, Meatloaf Cheddar & Biscuits, Auntie Paula's French Toast, and Salmon Hash. Tip: This is a popular restaurant so try to go at least 15 minutes in advanced to line-up. Otherwise, you'll end up waiting for an hour.
10:00AM – Tasty 'n Sons is in a great quintessential Portland neighborhood called N. Williams so just walk around the area and enjoy the different stores.
11:00AM – Today is an immersion into the amazing PDX food scene so be ready to taste a lot. Have one of the best ice creams you'll ever taste in your life at Salt & Straw.
12:00NN – Portland is all about the food trucks. Head on over to Guero and order the No. 3 Torta.
2:00PM – A second snack is in order. Head on over to Pip's for some seriously amazing doughnuts. Don't forget to get the Bacon & Maple Doughnut and Matcha Tea. Tip: Pip's closes at 4PM so make sure to go before then.
4:00PM – You might be having a bit of a food coma at this point so walk it off and head on over to the Tilikum Bridge to do some brisk walking.
7:00PM – Portland is NOT about snooty fine dining. Instead, PDX is into laid back casual dining that is all about the good food. Have dinner at Le Pigeon and make sure to order the burger–it's consistently ranked as one of the best in the city. Reservation is a must!
Day 3 (TUESDAY) – The Best of Both Worlds
10:00AM – The best part about Portland is how close it is to enjoy some natural wonders. Head on over to the Multnomah Falls and enjoy the scenery.
4:00PM – In Portland, you can be outside the city and enjoying nature one minute, then having fun downtown the next. Go to Union Way in front of Ace Hotel to do some window shopping.
6:00PM – Have dinner at Hot Lips Pizza at the Eco Trust Building. Note: Other blogs and websites will recommend other pizza places. But I specifically took my friends here because Hot Lips Pizza's concept is much more unique to Portland given its focus on Fresh, Local, Organic, Seasonal, and Sustainable ever-changing menus.
Day 4 (WEDNESDAY) – Foodie Day Part 2
The Waffle Window
8:30AM – 10:00AM – Portland is the #1 food city in America so naturally, this trip needs more than one day of pigging out. For breakfast, get waffles at The Waffle Window and a sandwich from Fried Egg I'm in Love.
1:00PM – Go downtown and hit up the Food Pods
3:00PM – A second cup of coffee is in order. Head on over to Coava. Tip: Coava is near two buildings called Rejuvenationand Grand Marketplace. Walk off the carbs and do some window shopping here.
4:00PM – Have dinner & drinks at Multomah Whiskey Library. NOTE: Leave the kids at one of PDX's awesome day care areas such as PDX Play Date.
Day 5 (THURSDAY) – Wine & Beer Day
9:00AM – Today is all about wine and beer tasting. But first, have breakfast at Gravy and don't forget to order the Corned Beef Hash.
11:00AM – Do the Wine Tasting at Stoller Winery. NOTE: Not everyone can spend the day hitting up several wineries. And if you could only go to one, I recommend Stoller Winery because their concept is unique to Oregon.
12:00NN – Have lunch at Red Hill's Market
3:00PM – Visit Rogue Farms and do some beer tasting
6:00PM – Have dinner at Burgerville
Day 6 (FRIDAY) – Seasonal Activities
Wooden Shoe Tulip Farm
9:00AM – Portland has four seasons so the places that you can see and do are dependent on which month of the year you are planning to visit. Since my friends went during Spring, I had them go to the Wooden Shoe Tulip Festival. There are all sorts of festivals from lavender to beer!
12:00NN – Head back to the city and have lunch at Old Salt Marketplace
3:00PM – Drop by Powell's Bookstore to buy some souvenir and just get lost in the thousands of books on display
5:00PM – It's almost time to say good-bye to the city so head on over to Pittock Mansion and go straight to the garden area to enjoy an amazing city view
7:00PM – Our friends requested to have dinner at Hot Lips Pizza (that's how much they loved that place). But go and try another dinner place such as Ned Ludd.
Day 7 (SATURDAY) – The trip is over so cap it off with a trip to the Portland Saturday Market