Waves and Wines, Cascade Peaks and Waterfalls
Experience the best of Oregon in nine unforgettable days, where ocean waves, vineyard landscapes and mountain peaks create a journey rich in scenery and flavor. Begin along the rugged coastline of Oregon Coast, where sea breezes, dramatic headlands, and iconic stops like Haystack Rock in Cannon Beach set the tone for the adventure. Head inland to the rolling vineyards of the Willamette Valley, where you can sip world-class Pinot Noir and savor fresh farm-to-table cuisine. Continue east toward the snow-capped peak of Mount Hood, where alpine lakes, orchard-lined roads, and scenic byways invite exploration. Then head back to Portland through the lush landscapes of the Columbia River Gorge, known for its forested trails and spectacular waterfalls, including the iconic Multnomah Falls.
From coastal waves to vineyard vistas and cascading mountain waterfalls, this nine-day Oregon journey showcases the incredible variety of landscapes that make the state such a memorable destination.
Lyn from Louisiana asks:
‘I am planning a trip to Oregon in September for about 9 days. We’re looking to spend a couple days on the Oregon Coast. We really only want 2 days of our trip to traveling time, so I prefer something not too far apart that all my time will be on the road. Any must sees? I generally prefer small towns with charm and not so much big city life.I would also like to know more about tours, so my husband can enjoy the trip too. It sounds as though we have two airport options, I’m leaning towards Eugene, again prefer not too big of a city. ANY help is appreciated.‘
First, we’ll tackle the easy question:
Yes, Eugene airport is an option. Eugene might be a bit more expensive, but not too bad. The Portland Airport is actually relatively small and you skirt the city on freeways to get out of the area. It might work to fly into Eugene and out of Portland to avoid extra driving?
Next: Oregon is a big state. This itinerary will lead you to Waves and Wines, Cascade Peaks and Waterfalls.
Day 1-3 – From Eugene head toward the Oregon Coast via Newport Oregon, Depoe Bay and on up the coast to Lincoln City and either Baywood Shores or Brey House B&B (3 hours driving)
- Yaquina Head Lighthouse and the Yaquina Head Outstanding Natural Area. The tallest lighthouse you can find along the Oregon Coast. Featured photo
- Depoe Bay Whale Watching Center
- Lincoln City revels in kite festivals and glass blowing, saltwater taffy and music festivals. Be on the lookout for the colorful glimmer of hand-blown glass floats when exploring our Oregon Coast beaches
- Support local artists with Tax free shopping
Head back into the heart of Oregon’s Wine County only about an hours drive.
Day 4-6 -Pair your exploration of Oregon’s wine country with a stay in one of our member Willamette Valley Bed and Breakfasts. I’ve pinned A’Tuscan Estate Bed and Breakfast for reference as they are in the heart of Oregon’s Wine country. Oregon independent inns combine uniquely styled accommodations with locations that are close to the valley’s many attractions, many of which go far beyond award-winning wine, including:
- A world famous wine country that offers 440 wineries, producing award-winning Pinot Noir, Pinot Gris and Riesling using the grapes from 647 vineyards in the region
- Organic farms providing livestock and produce for fine dining at area restaurants and selling at their own farmers markets
- Several craft breweries, cideries, meaderies & distilleries
- Culinary events that pair the food and drink of the valley with its wonderful sights
- Urban attractions in the college towns of Eugene and Corvallis
- An active arts culture & museums can be found throughout the region
- Scenic drives & biking routes that connect it all on back roads and through covered bridges
- Silverfalls State Park
- Salem State Capital Mall
- Support local artists with Tax free shopping
Mt Hood and the Columbia River Gorge
Day 7-8: 2.5 hours Northeast from the Willamette Valley to the Old Parkdale Inn Bed and Breakfast near Mount Hood.
A spectacular view from the Solera Brewery Beer Garden – photo credit Old Parkdale Inn
- Scenic country backroads past nurseries, Christmas Tree farms
- Timberline Lodge
- 36 Hours near Mt Hood
- Support local artists with Tax free shopping
Back to Portland through the Columbia River Gorge
Day 9 – Explore the Columbia River Gorge
- Historic Columbia River Highway
- Columbia Gorge Sternwheeler Cruise
- Multonomah Falls
- McMenamins Edgefield Hotel – Dinner and your last night in Oregon.
The innkeepers with the Oregon Association of Independent Inns are certainly the best resource to ask what to see, what to do, and where to eat near them.
Flying in and out of Portland would only be adding a few extra miles, same number of days, and you’d certainly see a bit more of our diverse state.
- Portland to Lincoln City
- Lincoln City to Newport to the Willamette Valley
- Willamette Valley to the Old Parkdale Inn
- Old Parkdale Inn through the Columbia River Gorge and back to Portland.
Hope this has stirred the adventurous traveler in you. And we look forward to welcoming to Oregon. Do tell our innkeepers OBBG referred you and we’d love to see photos of your adventures.
Oregon Association of Independent Inns are ready to share Oregon with you: it’s environment, culture, and heritage. Combine gracious hospitality with ambiance at an inspected and approved member of the Oregon Association of Independent Inns.
Gift certificates are no longer available for purchase through our organization. We encourage you to contact our member inns directly to purchase gift certificates.
If You Currently Hold an OAII or OBBG Gift Certificate:
- Your gift certificate does not expire
- Certificates may be redeemed at participating Oregon Association of Independent Inns properties.
Thank you for supporting Oregon’s Independent Inns and lodging properties over the years. We’re grateful to everyone who has shared the gift of lodging through the OAII Lodging Gift Voucher Program.
As of June 1, 2026, the Oregon Association of Independent (formerly the Oregon Bed and Breakfast Guild – OBBG) discontinued the program, and gift certificates are no longer available for sale. However, existing gift certificates remain valid and may still be redeemed.
The Oregon Association offers a wide variety of inns, from a small guest cottage or two-room bed and breakfast to a larger country inn or dude ranch. If you need assistance locating a participating property or have difficulty redeeming your certificate, please contact us—we’re happy to help.
Important Notes:
- All OAII properties accept association gift certificates. Click here to view participating properties.
- Gift certificates are treated as cash and cannot be replaced if lost, stolen, or destroyed.
- Certificates may only be redeemed at active OAII properties
- Individual property policies apply, including restrictions on availability, packages, or special offers.
Questions or Assistance:
If you have questions about redeeming a gift certificate or need help planning your stay, please contact E-mail info@obbg.org or call OAII at 503-893-4210. Please leave a message as this line is monitored by our busy innkeepers.
Since 1989, the Oregon Bed and Breakfast Guild has served as a statewide information network for its member properties, providing a unified voice for the industry with state regulatory and tourism agencies.
Now known as The Oregon Association of Independent Inns, we’re the same trusted organization, with a new name, a fresh look, and an expanded focus on independent lodging properties beyond traditional bed and breakfasts. Member properties represent a wide range of accommodations, from small guest cottages, cabins, and intimate two-room B&Bs to larger country inns, boutique hotels and dude ranches.
