5-Day Tour: Oregon Coast, Mt. Hood, Willamette Valley, & Columbia Gorge

5-Day Tour: Columbia Gorge, Mt. Hood, Willamette Valley, Oregon Coast & Portland
‘Oregon Bucket List’ Tour

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Portland residents often boast “only an hour to the mountains and only an hour to the coast!” To really experience all Oregon has to offer from shoreline to alpine timberline would take a lifetime, but this epic tour combines the region’s gorgeous natural calling cards into a journey you’ll likely never forget. From waterfalls to snowfall and splashing waves to wine swirling in the glass – this is the ‘Portland Bucket List’ tour!

Tour Overview



Tour Dates 2020


Tour Price

$3000 per person.
Additional $300 single-occupancy rate required for solo travelers.

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Tour Details


Day 1: Columbia River Gorge National Scenic Area & Hood River

Waterfall Alley, Hood River wineries, Rowena Crest, & Celilo

Your journey begins just east of Portland as you enter the Columbia River Gorge National Scenic Area with less than a 30-minute drive. We’ll hit the trail at Latourell Falls in the morning, and make stops at two other waterfalls in “Waterfall Alley.” This will include a stop at the tallest in the region, Multnomah Falls. Your guide will share stories from the formation of the gorge to the many ways locals play here today, with plenty of scenery in between. Moss hangs from the trees, and cold mountain water tumbles down the rocks, with all of this natural beauty highlighted by the scenic highway.

Lunch will be served at a winery in the Hood River Valley, where warmer temperatures allow for a wide array of grape varietals to grace your glass. East of Hood River, there’s more scenic highway to explore, and the trip out to Rowena Crest Viewpoint highlights the climatic change this day brings – here, east of the Cascade Mountains, the landscape has changed dramatically, offering up a more austere and rocky scene of grasses, scrub oak trees, and ponderosa pines. Enjoy some free time this afternoon in Hood River before gathering together for a welcome dinner in downtown Hood River.

Walking Distances:

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Day 2: Mt. Hood, Willamette Valley, & McMinnville

Mount Hood hiking, Timberline Lodge, Willamette wineries, & more!

Today we climb! Making your way around the east side of Mt. Hood, there will be opportunities to stop for mountain views, and a hike in the woods. After some good trail-time alongside mountain hemlocks and huckleberries, we’ll lunch in style at the historic, Depression-era Timberline Lodge at 6,000’ of elevation, and a chance for an exploration of the alpine landscape.

Descending from the famous lodge, you’ll skirt the edges of Portland to visit wine country in the Willamette Valley. Pinot noir is king in this valley, as it’s the grape that put the region on the wine map, but there’s plenty for all to enjoy before we settle in to our overnight digs in downtown McMinnville.

Walking Distances:

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Day 3: Oregon Coast & Cannon Beach

The Coast Range, Tillamook Cheese, & the Pacific Ocean

This morning we travel over the Coast Range – nothing compared to those Cascades! – to our first encounter with the Pacific Ocean at aptly named Pacific City. Along what’s known as the Three Capes Loop, you’ll have sweeping views of the ocean, and a chance to hit the trails or battle your way to the top of sand dunes.

Grab a sample at the Oregon-icon Tillamook Cheese Factory and head north on famous Highway 101 around Nehalem Bay and up and over Neahkahnie Mountain, looking out over the endless ocean. Numerous state parks along this rugged section of coastline invite exploration as you near Cannon Beach, your home for the next two nights, with opportunities to walk the beach, soak up a sunset, or stock up on saltwater taffy!

Walking Distances:

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Day 4: Oregon Coast & Cannon Beach

Slow down in Cannon Beach, Ecola State Park, & Brews

Staying put in Cannon Beach today, your guide will provide hiking options and plenty of local recommendations, including a chance to walk in the footsteps of Lewis & Clark, who walked over Tillamook Head (now Ecola State Park) in 1805. A pub lunch may be your introduction to craft brewing, and galleries and shops offer plenty of coastal diversions for a relaxing day off the road. Get sand between your toes today with a walk to picturesque Haystack Rock.

Walking Distances:

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Day 5: Urban Portland Exploration

City touring, food trucks, & trip wrap-up!

The final day of our adventure finds traveling through the coastal forests back towards Portland, where your guide will provide an overview of history and local culture, including a stop for artisan donuts and a chance to lunch like a local at a “pod” of local food carts. If you are continuing your travels with a stay in the city, your guide will drop you at your downtown hotel, or at the airport for those making their way home this evening.

Walking Distances:

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The Pacific Northwest is waiting for you!

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Additional Tour Information

5-Day Tour from Portland: Columbia Gorge, Mt. Hood, Willamette Valley, Oregon Coast, & Portland Tour

Traverse the Mt. Hood National Forest, including a visit to historic Timberline Lodge.

Experience the extreme dichotomy of landscapes in Oregon: the verdant forests of Western Oregon, and the high desert of Central Oregon.

Relax near the jewel blue waters of Crater Lake and learn the volcanic history of Mount Mazama.

Feel the mist of waterfalls at Silver Falls State Park in the Cascade foothills.

Savor pinot noir in the world-renown Willamette Valley wine country.

You'll sleep soundly in the heart of Olympic National Park in private, comfortable mobile mini-cabins outfitted by our friends at ROAM Trailers! All lodging costs are included in our pricing.

You'll be guests of ROAM Beyond, staying in Homegrown Trailers featuring a queen bed (plus bunks), robust solar power systems, advanced battery storage, hot water and shower, induction cooktop with pots & dishes, cold refrigerator and freezer, plenty of power for lighting and charging devices, plus a self-contained toilet. Linens with a warm comforter and duvet cover will be included along with pillows, towels, and biodegradable soaps.

Join a small group (a maximum of 10 travelers total). This adventure is $1500 per person after all taxes.

This trip does require, at minimum, that three travelers book any given date. If our trip doesn't reach it's three guest floor - all booked travelers will be notified in advance and refunded fully.

To book a public trip, we ask for $250 to reserve your spot on the trip. 60 days out we'll ask for a 50% deposit as we prepare for your trip. 30 days out we'll request the final balance.

Want to make your adventure private? Prices below are before WA Sales Tax (10.1%). To inquire about private trip dates, give us a call!

1 person: $4100/person

2 people: $2400/person

3 people: $1900/person

4 people: $1600/person

5 people: $1400/person

6 people: $1250/person

7 people: $1150/person

8 people: $1000/person

9 people: $975/person

10 people: $950/person