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View & Vine · Custom Itinerary
The Leifer Family
in Willamette Valley
Sunday, September 20–September 26, 2026 · Willamette Valley & Oregon Coast
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Wine country welcome
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Your Trip
A week in Willamette Valley
Travel Brief
At a glance
- Sunday, September 20: Come up from Ashland on the route through McMinnville, then about twenty minutes north through Carlton to the house.
- Monday, September 21: A short loop close to home, with a town stop in the middle so no one is in the car for long.
- Tuesday, September 22: Ninety minutes west on Highway 18 to Pacific City and Neskowin.
- Wednesday, September 23: Ninety minutes southeast for waterfalls and gardens.
- Thursday, September 24: The family heads home this morning, and the two of you drive to the coast, about two hours northwest.
- Friday, September 25: A leisurely morning, the headlands at Ecola, downtown, and the tidepools at sunset.
- Saturday, September 26: Breakfast at the inn, then the drive to PDX, about 1.5 hours.
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Where You're Staying
The Gables at Quandary Vineyard
Your luxury rental home sits on a hill in Yamhill-Carlton wine country, with four primary suites, a full kitchen, and vineyards in every direction. Quiet and rural.
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Where You're Staying
Stephanie Inn
A small luxury hotel right on the sand south of downtown. Rooms have fireplaces and soaking tubs; there's a complimentary wine and beer gathering in the late afternoon and a nightcap in the evening, beach cruisers to borrow, and a chef's breakfast each morning.
Trip Map
The whole route
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Arrival
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Sunday, September 20
Arrival
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In the Vineyards
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Monday, September 21
In the Vineyards
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Coastal Day Trip
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Tuesday, September 22
Coastal Day Trip
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Silver Falls & the Oregon Garden
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Wednesday, September 23
Silver Falls & the Oregon Garden
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To Cannon Beach
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Thursday, September 24
To Cannon Beach
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Cannon Beach
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Friday, September 25
Cannon Beach
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Home
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Saturday, September 26
Home
Practical
Good to know
Getting Around
You're renting two SUVs out of Medford, one per family. Choose something with a little ground clearance; a few of the winery and back roads near the house are gravel.
Traveling with a Little One
BabyQuip delivers cribs, high chairs, car seats, beach gear, and toys to the house, so you skip flying with the bulky things.
Priority Reservations
Most restaurants and wineries aren't bookable until 45 to 60 days out. I'll make your reservations for you as part of the service. The two to lock in as soon as you're ready are the Stephanie Inn spa treatments and, if you'd like one, a driver for your wine tasting day.
Documents
Confirmations
The Gables at Quandary Vineyard
- Confirmation
- 73458357005623 (Expedia TAAP itinerary); VRBO confirmation 4955423
- Booked through
- Expedia TAAP
Stephanie Inn
- Confirmation
- 63709SG090381
- Booked through
- Stephanie Inn (direct, via Fora)
Self-booked by the family (two vehicles)
- Confirmation
- [family self-booking â not via View & Vine]
- Details
- Two SUVs with ground clearance, one per family. The family is booking these directly. A single View & Vine Enterprise Standard SUV was quoted ($1,137.23, quoted 6/9) but declined in favor of two self-booked vehicles.