When people stop by the Visitor's Center at Pioneer Courthouse Square, where I've volunteered since 2001, my number one recommendation is to Walk & Graze!
There are so many wonderful places to eat and drink in this city that it's a shame to waste all your stomach's capacity in one spot. Have a coffee, share a donut, sample something from a food cart, have another coffee, split an entree for lunch, get a kids scoop of ice cream, have a cocktail and an appetizer, enjoy a local brew, and if you've still got space, make a dinner reservation at a local hotspot, but save room for a nightcap somewhere with a view.
Portland is an extremely walkable city. Our blocks are half the size of a New York City block. The reason? Our city planners realized that corner lots command more revenue. Smart guys!
The area of town I'm most excited about right now is the newly revitalized "West End" of downtown (SW 12th Ave/ cross streets Washington & Alder). Within the past year or two some amazing restaurants have moved into this area making downtown a renewed hot spot for fabulous dining. Many of the restaurants in this area have an older sibling in other parts of town. In January of this year John Gorham opened Tasty N Alder (580 SW 12th Ave), a sister restaurant to Tasty N Sons (3808 N. Williams), considered by many to be the best Brunch spot in Portland. It thrills me to tell visitors that 5 (half size) blocks away they can eat at one of Portland's best brunch spots. Other amazing places in that locale are: Grüner (James Beard nominated chef & reliably spectacular dinner spot), Kask (modern saloon next door), Grassa (hand made pasta), Blue Star Donuts, Ruby Jewel (ice cream),Multnomah Whiskey Library (a sight to behold with it's 1500+ bottle collection), Lardo (artisinal sandwiches), and the place I'm most excited about, a second cafe by local roaster Heart, which opened in Nov 2013.
The other major dining Hotspot du jour is SE Division - so much happening on that street right now. Of course there's Pok Pok, and my personal fave Ava Gene's(named "Restaurant of the Year" by Portland Monthly Magazine, Oct 2013, and named #5 Best New Restaurant in America by Bon Appétit, Sept 2013). It's owned by Stumptown Coffee Roaster's own, Duane Sorenson.
Other fun areas with high density fine dining (and when I say "fine" I don't necessarily mean "fancy" rather amazing food lovingly prepared by true artisans; think FLOSS - Fresh, Local, Organic, Seasonal, Sustainable) - NE Alberta & NE Killingsworth, North Mississippi, Pearl District, NW 23rd & 21st. Oh, and did I mention Food Carts? The City of Portland has issued over 700 licenses for food carts, many of them located in "pods" (defined by more than 2 food carts together, kind of like a gaggle of geese or a pride of lions... a pod of food carts). There are downtown pods on 10th & Alder, 5th & Oak, and many further out, such as North Mississippi & Skidmore and SE Belmont & 46th.
If you follow the James Beard Awards we've got a few local stars. I recently compiled a list, for my own interest, and can honestly say, you can't go wrong picking a restaurant based on this list. Local James Beard Winning/Nominated Chefs
My favorite restaurant in Portland right now? Atuala - a stunning Catalonian tapas restaurant located just off Northwest Portland's restaurant row on 23rd Place.
Another thing I recommend visitors do is take the Portland Streetcar (NS Line) on its entire loop from downtown, through the Pearl District, to NW 23rd Street (one of my favorite boutique shopping streets with great little cafes and shops in converted Victorian houses... think Nob Hill), back into downtown, by Portland State University, and down to the South Waterfront, where you can hop off and take the OHSU Aerial Sky Tram for a 3 minute ride up the hill for a fantastic view of the city & surrounding mountains. I think it's a great overview of the city that can be done very cheaply and you have the ability to hop on and hop off as much as you want. An all day Streetcar ticket costs $2.50, or if you're using Light Rail (MAX) or Buses, you can get a comprehensive Tri-Met Day Pass for $5.
And of course, Portland is the City of Roses, so a visit to the International Rose Test Gardens (free) is always a wonderful choice.
Check out Travel Portland's website for trip planning advice, other great options for things to do, and hotel suggestions.
If you have questions, please feel free to email me. I love to help people get the most out of their Portland experience!