After receiving many requests for recommendations, I decided to do my own “weekend” in Portland for all to access. Having moved back to Hawaii last year, the best places I mention here are exactly where I head to the first chance I get. The best part is you don’t need a car! Book your ticket or get in your card and head to this foodie destination now.
FRIDAY
5 p.m. Once you arrive on a Friday afternoon start your libations early with Happy Hour at Clyde Common in the up and coming “west end” part of SW Portland. A limited cocktail list is just $5 and their burger is just $6. Their known for their popcorn & fries. After years of attending this swanky restaurant bar I’m never disappointed. In the basement of the Ace Hotel, it attracts an audience that’s friendly to visitors and locals alike.
6 p.m. One of my favorite shops to peruse is just around the corner from Clyde, Frances May stocks all the designers you love but might not frequently purchase. Acme, Rachel Comey, Vena Cava, and you get the idea. Don’t skip the jewelry case, with lots of unique designers from New York and beyond you don’t see anywhere else in Portland. I’m somewhat of a dedicated experienced shopper, but even excluding that Buffalo Exchange in the Pearl district is by far my favorite place for unusual designer pieces, stellar boots, and you might even score a cool bag if you time it right. Open until 9pm most nights to boot.
8 p.m. Head over to Grassa for a casual and cheap place for delicious made in-house italian pasta. With their selection varying nightly and using fresh ingredients it’s sure to please. Just a block away is a cavernous pre-prohibition era bar Kask. It buts up against the yummy German eatery Gruner on Alder street. Sharing it’s kitchen with Gruner it serves charcuterie plates that go perfectly with their long list of specialty cocktails. Like most bars in Portland, their selection of whiskeys, beers, and wines are top-notch.
10 p.m. Known for it’s rich musical scene, be sure to see who’s playing where. Mississippi studios, Aladdin Theater and the Wonder Ballroom to name a few. The Crystal Ballroom is one of the oldest venues around, with an original floating floor perfect for dancing on. Known for it’s kitch decor and 70s style eats, the Doug Fir Lounge is a quick jaunt across the river to the SE part of town.
SATURDAY
10 a.m. Depending on how late you like to sleep in, start your morning at Tasty n’ Sons in the NE part of the city. Like most delicious places in Portland, they don’t take reservations. So you’re looking at waiting at least 20 mins on a weekend for seat. But that’s ok, sip coffee while you wait. With the same owners as Toro Bravo, the potatoes bravas is my every visit must. You can’t go wrong with anything on the menu, scouts honor. They serve everything family style, and everything arrives once it’s done, so get friendly with your guests and expect to share.
12 p.m. the Portland Farmer’s Market at PSU (Portland State University) is a don’t miss. Opening hours depend upon the time of year you’re visiting, but they are open generally from 8:30am-2pm mid March through mid December. It’s packed full of visitors and locals alike, beware of strollers blocking your every move. You’ll find amazing vendors from all over the state with samples galore. Bring back some hazelnuts, specialty salts, and cheeses. There are made to order food vendors too if you’re finding yourself peckish.
2 p.m. Walk off your indulgences or take the street car down near NW 3rd & Everett streets. There you’ll find a magical oasis inside Portland City proper, at the Lu San Chinese Garden. It’s absolutely stunning, and with a tea shop you can enjoy a relaxing couple of hours.
4 p.m. If you’re finding yourself afternoon stomach grumbles make your way to SW 10th & Alder streets. There you’ll find one of the large gatherings of food trucks. With so many options from Scottish fish & chips, Korean fusion burritos, and handmade Chinese noodles, let your curiosity get the best of you.
5 p.m. Just up the road on Alder you’ll find your way to the cutest home goods shops Canoe and Alder & co. Canoe specializes in perfectly designed goods for the home and office. Heath ceramics, Pendelton blankets, Comme des Garcons wallets just get your desire whet. Alder & co.’s owners travel to Europe and Japan seeking out unique linens, jewelry, kids toys, and clothing for the woman with refined taste. Odessa is another favorite slightly out of reach boutique full of designers I covet like Isabelle Marant, and other lesser well known french designers. Who said you said you can’t have desert before dinner? Cacao next to Odessa is a chocolate lovers dream. Drinking chocolate and coffee to sip as you people watch the parade of interesting characters calling PDX home.
6 p.m. If you’re energized and the weather is holding up for you, make your way either by street car or by foot up to NW 23rd street. Along 23rd street there are lots of adorable cute shops and one of three locations of Salt & Straw ice cream shops. You’ll know you reached your location when you spot the line wandering out the door. Honey Lavender and Salted Carmel are my must haves.
8 p.m. with a seemingly infinite amount of amazing restaurants popping up everyday in Portland how do you decide just where to eat? I go with what I crave, and I love Pok Pok. Another spot that doesn’t take reservations, either go early or go late. And with their partner “waiting area” the Whiskey Soda Lounge, it’s not too shabby of a place to spend a saturday night. Order the house drink and my all time favorite cocktail the Tamarind Whiskey Sour. Pok Pok makes their own vinegars, and this drink makes their unique flavors shine.
10 p.m. If you haven’t had enough of Salt & Straw ice cream, you’re in luck, there’s one just down the street from Pok Pok.
11 p.m. If Jazz is more your thing, Jimmy Mak’s in the Pearl is always going on off on Friday & Saturday nights. Live acts from Portland and impressive musicians stop in for an appearance from all over the nation. Cozy and with late night food bites, this place is rocking past the 12 o’clock hour. Finding good live music in stumptown isn’t hard, you’ll likely stumble upon it without even looking.
SUNDAY
10 a.m. Sleep in without worry. Irving Street Kitchen takes reservations. Specializing in a bit of southern taste like delicious chicken & waffles, they also cater to the less glutenous appetite with delicious french style scrambled eggs with crab. Fabulous specialty cocktails too.
12 p.m. Take a stroll through the Pearl district shops be sure to stop at Thea’s Vintage Living, Moule, Jonathan Adler, making your way to the spot of divine doughnuts at Blue Star.
If you still have time, take a ride through the gorge for some spectacular sights. You can imagine just how magical it must have been for Lewis & Clark.
Where to stay? I highly recommend finding a place using the popular site Airbnb. I recommend staying downtown near the Pearl district with easy access to public transport using Trimet. In fact you can even take the light rail train called the MAX directly from the airport to downtown. The Ace Hotel is a fun choice. What are you waiting for? Pack your bags!
Pualana 
Great post! I was actually going to ask you for some suggestions on visiting Portland after reading your last post. I will be here in just a few weeks on my honeymoon. So sad to hear that you aren’t living here any more. I would have loved to have gone shopping with you. Hope you are doing well and I look forward to reading more from you.