Day 1 - Vancouver to Seaside, OR (1 night hotel)
* stop at Mount St. Helens Visitor Centre if possible
Day 2 & 3 - Seaside to Newport (2 nights timeshare)
* Ecola State Park, Cannon Beach
* Yaquina Head Natural Area, Lighthouse & Bridge
* Devils Punchbowl State Natural Area
* Nye Beach
* Cape Foulweather
Day 4, 5 & 6 - Newport to Sunriver (3 nights timeshare)
* Crater Lake National Park
* John Day Fossil Beds National Monument
* Oregon Observatory
* High Desert Museum
Day 7 - Sunriver to The Dalles (1 night hotel)
* Timberline Lodge
* Hood River surfers
* Fruit Loop
* Multnomah Falls
Day 8 - The Dalles to Oliver, BC (1 night hotel)
Day 9 - Oliver to Kelowna (1 night hotel)
* vineyard tours
Day 10 - Flight from Kelowna to Winnipeg
I've done all of this multiple times in many variations. Here are some comments:
First of all your dates are important. Looks like roughly June 9-19 give or take a day. That is the perfect time to see Mt St Helens before all the snow is gone and while the wild flowers are still blooming. On the other hand, Crater Lake may be still snowed in. You would need the north entrance to be open and that doesn't happen until sometime in mid-June or later, especially this year. Their snow plows all broke down last winter and while they have one working now, it's still working to catch up. In addition, they got way more snow than normal. If Crater Lake is a priority, call ahead first to make sure the north entrance is open. The road around the rim will not be open then so even if the north entrance is open, you would be limited to driving the west side and hoping that enough snow has melted to see over the walls of snow; again, ask before driving down. The south entrance is always open but is a good 3+ hour drive each way from Sunriver.
Sunriver is in a gorgeous area and I suggest you focus on that area versus driving multiple hours elsewhere. With only a couple of days there, you just don't have enough time to see everything. Plan on a return trip. John Day painted hills area is beautiful, but I'd save it for another trip when you have more time. It's a 2 hour drive each way from Sunriver. Focus instead on the mountains out the back door of Sunriver.
The Three Sisters Wilderness is out the back door of Sunriver. The Cascade Lakes highway should be top of your list to at least drive, but there are tons of trails all along for some easy hikes if enough snow has melted. Even if there is still snow around, the views are spectacular.
https://www.visitbend.com/wp-content/uploads/2018/03/cascade-lakes-byway-map.pdf.
https://www.visitbend.com/points-interest/cascade-lakes-national-scenic-byway/
Bordering Sunriver to the north is Lava Lands National Monument (now part of Newberry Crater NM). The top of Lava Butte has one of the best views around. There is a visitor center and some easy trails through the lava flows as well for both interesting geology and spectacular views.
Tumalo Falls is a nice short hike west of Bend; probably less than an hour from Sunriver. Further west is the town of Sisters which is a nice little town for shops and restaurants and scenery.
McKenzie Pass and other areas north of the Three Sisters may not be open; typically it opens the 3rd Monday in June. So another reason to come back for a fall trip perhaps?
In Sunriver itself, the bike path is extensive and scenic. Walk or bike the section along the river from The Pines; head left down to the river and then back up the hill to the Lodge for a nice couple hour walk. Bikes come with a stay at The Pines so if you decide to hit the bike trail, make sure to pick up a map; it can be pretty confusing if you venture out into the other areas. The walk goes by the nature center which has the observatory in it. If you go for the programs at night, parking can be an issue so some flashlights will come in handy if you have to walk up the road or decide to walk over along the bike path.
For good hike information in Oregon, I like:
https://www.oregonhikers.org/field_guide/Main_Page. choose your difficulty level and location.
From Vancouver to Seaside is doable in a day. However, the side trip to St Helens and back makes it too long to do much besides drive. Consider instead staying overnight in Castle Rock along I-5 north of Longview. That would give you time to drive up to St Helens to Johnston Ridge Observatory. Watch the film and then walk the Boundary trail from the visitor center out about a mile or less; the views are from the beginning so go as far as you want. Then head back down to the freeway where you will find plenty of motel choices. The next day, it's a short distance south to Longview where you should take the bridge over the Columbia to Highway 30 down to Astoria and then down Highway 101 to Newport. Driving time is about 4.5 hours which should give you time for stops along the way. Along the way: Ecola State Park is nice but I suggest you look at Hug Point or Short Sands beach as similar but easier to get to side trips on your drive down the coast. If you want to walk the beach at Cannon Beach, park at Tolovana at the south end of Cannon Beach and walk from there; easier parking and access to the beach.
At Newport, you only have one day so it's difficult to choose. Cape Foulweather and Devil's punchbowl have names that sound better than the reality. Skip them. Yaquina head is great as well but my favorite spot is half an hour south at Yachats (pronounce Ya hots). Smelt Sands State Park is a small parking area with access to the 804 trail that runs along the top of the bluffs. It's a volcanic rock bluff with surge channels and waves crashing up high; really spectacular. Just south is Cape Perpetua with more trails along the bluffs. For a walk on a sandy beach, Beverly Beach north of Newport is nice.
You will want to come back. April or May for the ocean or eastern Oregon and fall for the mountains. Too many things to see and not enough time.
Sue