From your starting point in Portland, you will find yourself in a city ringed by old growth fir forests, snow-capped volcanoes, ancient cliffs adorned with tumbling waterfalls, fertile farmland and vineyards, and hundreds of miles of undeveloped coast ripe for exploration. This luxury Oregon road trip provides an unmatched concentration of stunning, diverse Pacific Northwest landscapes enriched by unique adventures and connections with local producers.
Days 1 & 2
Portland is a perfectly situated starting point for your luxury Oregon adventure, but it is also a destination in its own right. Your downtown hotel is in a prime location to hit the classic landmarks: the International Rose Test Garden, the World’s Smallest City Park, or the city block taken up by Powell’s, America’s largest independent bookstore. We will make sure you have plenty of reasons to cross one of the city’s nine iconic bridges to experience the funky neighborhoods, arts districts and expansive urban greenspaces that make Portland truly unique.
Drive out to Sauvie Island, an agricultural hub just 10 miles outside of Portland’s city center. Here, in the midst of a 12,000 acre wildlife reserve, a beekeeper and passionate pollinator advocate will help you suit up and show you what it takes to maintain a healthy hive before preparing a lovely orchard picnic with a honey and cheese tasting next to the farm’s flower fields, with views of three snow capped volcanoes in the distance. Return to the city in the afternoon for a different type of culinary experience. We reserve a coveted lawn chair in Han Oak’s courtyard or a place at Naomi Pomeroy’s communal table at Beast. If you are hoping for something more casual, hop on bikes with a local guide and sample dishes from Southeast Portland’s best food carts.
Columbia River Gorge
Days 3 & 4
This morning you’ll bid farewell to Portland, but not before getting your caffeine fix with a local coffee aficionado. Stop at some of the city’s most-loved cafes and micro-roasters to sample award-winning brews and get the inside track on how to perfect your own morning cup.
Just outside the city limits, you enter the Columbia River Gorge, a geological wonder that cuts a deep path through the Cascade Mountains. Follow Historic Highway 30, a narrow, winding road that is edged by towering trees and steep cliffs dripping with waterfalls to your right and sweeping views of the mighty Columbia River to your left. Fill the afternoon with short walks down to the misty base of a waterfall or up to a rocky viewpoint before reaching the city of Hood River, the cultural and adventure hub of the Gorge.
Enjoy a full day exploring these dramatic landscapes with a guided bike (or e-bike), traveling on a car-free section of the same Historic Highway 30. Ride past orchards and vineyards, and straight through the gorge’s rocky cliffs at the Mosier Tunnels. Hang onto your bike to visit vineyards and farms in the afternoon or hit up a locals’ favorite microbrewery while you watch windsurfers and kite boarders on the Columbia waterfront.
Days 5 & 6
It might be tempting to take another pass through the gorge to get to the coast, but we recommend heading south out of Hood River, around Mt. Hood. The 11,280’ snow-capped giant almost looks out of place looming over the orchards and organic farms that dot “The Fruit Loop,” but the volcanic soil is key for this agricultural wonderland that sits between the gorge and the mountain.
As you wind your way around the mountain, take a short detour up to the Timberline Lodge, which you may recognize as the Overlook Inn from the movie The Shining. This Historic Lodge is a great jumping off point to hike a bit of the Pacific Crest Trail or watch skiers on the Palmer Glacier, which is open year-round. From the Timberline, descend through the thick trees of Mt. Hood National Forest, skim past Portland and over the Coastal Range to Oregon’s most refined beach town, just in time to see the sun set over Haystack Rock.
Your time in Cannon Beach can be as active or relaxing as you would like, but we would recommend exploring Ecola State Park and Tillamook Head with a naturalist guide. In addition to being one of the most scenic points on the Oregon Coast, this was the furthest point reached by Lewis and Clark as they traveled in search of the Pacific Ocean with the Corps of Discovery.
Days 7 & 8
Today’s drive South along the Three Capes Scenic Loop will take you over rugged, rocky cliffs and along expansive stretches of sandy beach punctuated by idyllic communities and hamlets, each with their own distinct character. Thanks to a state bill banning private beach ownership passed in the ‘60s, you can feel free to explore “the people’s beach” freely. With so much to see, it will likely be well into the afternoon when you arrive at the Headlands Lodge in Pacific City, set against the Cape Kiwanda Natural Area. We’ll ensure you experience Pacific City like a local, starting with a hike to a secluded beach bonfire complete with s’mores and starry skies.
You have your pick of interesting ways to explore the central coast. Head out to a secluded bay on a quest for clams and cook up your spoils over an outdoor fire, or if you prefer, over the chef’s table at a local restaurant. Hop on a local’s dory for a day of crabbing or fishing in the coastal estuaries. Fat bike through the ghostly remains of a washed away town at low tide, or look for seabirds as you kayak through marshy wetlands. No matter how you spend your days, you can end it with a Pacific sunset over Cape Kiwanda.
Days 9 & 10
Enjoy a final morning on the beach before heading inland for good. Willamette Valley Wine Country is less than an hour’s drive, but feels a world away from Pacific City. Your homebase here is a lovely estate on the Black Walnut Vineyard. You can drop into tasting rooms en route from the coast, but you will spend a full day with a local wine expert who will guide you to their favorite vineyards and tasting rooms with a stop for a lunch featuring hyperlocal produce and foraged ingredients. For something different, we can upgrade the experience to an aerial wine tasting adventure. Take to the skies in a private helicopter to be chauffeured between tasting rooms while taking in the stunning scenery of Oregon’s wine country.
The Willamette Valley’s tight-knit communities of talented producers have been able to draw in top chefs from around the country looking to leave their mark on this growing culinary hotspot. We’ll be happy to set you up with a tasting menu made for mushroom lovers at the Joel Palmer House or a seating at local favorite Thistle to commemorate the final night of your Oregon road trip adventure.