KonaJoe

Been to Portland itself a number of times though not for 15 years. Looking to spend 10 days covering Portland (3-4), some wine country and coastal areas in June. I would fly in and out of PDX but otherwise pretty open to cover ground. What is a worthwhile loop and some stops along the way. We are 60+ and live in HI so this is different coastal country but we love history, little towns, beer/wine, good food, music, modest hiking, staying in B&Bs or little hotels. Be up for an MLS game if we can swing it. I have done Bend, Mt Hood and the Gorge before but have not really hit Wine country and no coast at all. Suggestions?

Gardyloo

It's not terribly complicated. Here's a map (one of many possible) that you might research - https://goo.gl/maps/HMt3fBpLFxmLSCzU9 . Google the places on it.

This counterclockwise loop starts in Portland then follows the (historic, scenic in parts) north shore of the Columbia River to its (awesome) mouth at Cape Disappointment. It then crosses back into Oregon and historic Astoria, then down the coast from there. Some highlights include Ecola State Park near the popular town of Cannon Beach, scenic Cape Meares, a couple of picturesque towns in Yachats ("ya-hots") and Depoe Bay, along with numerous spots to stop and look at the scenery.

The route would then head inland from Florence to the Willamette Valley. I'd follow OR Hwy 99W north through Corvallis and on to McMinnville, which can serve as a base from which to explore the center of the wine country in the northern valley. You might look at staying at McMenamins Hotel Oregon in McMinnville for funky and fun surroundings. Hotel Oregon Hotel - McMenamins

There are umpteen guides to the wine district, but you should also set as a priority securing lodging reservations in key coastal towns such as Cannon Beach; by midsummer many places require multi-night stays.