Plan Your Own Adventure: 4-Day Food & Drink Tour from Portland, Oregon

Plan Your Own Adventure: 4-Day Food & Drink Tour from Portland, Oregon

Create Your Own Portland Multi-Day Foodie Adventure!

4 Days | 3 Nights

Another installment of our “Plan Your Own Adventure” series – get to know the Pacific Northwest like a local as we lay out the basic structure for you to build your own escape. In this edition, explore Portland – the Rose City, Bridgetown, Stumptown – and its eclectic neighborhoods before heading out to the rugged Oregon Coast, breathtaking Columbia River Gorge and bountiful Willamette Valley.


Explore Portland and its eclectic neighborhoods

Visit historic Astoria and beachcomb on the Oregon coast

Sip Oregon’s famous pinot noir

Hike to stunning waterfalls in the Columbia Gorge


Day 1 | Urban Portland

The “Rose City” is adored by nearly all who visit: Portland is unique, vibrant, sustainable, and beautiful. Enjoy easy-to-come-by iconic views of the surrounding volcanic peaks, waterways, and dense forests while exploring charming/quirky neighborhoods and urban parks. Some refer to Portland as the most environmentally friendly or “green” city in the United States.

Spend your first day in Portland getting to know the city – sights, sounds, and tastes. From its eclectic neighborhoods to its hip, urban downtown and Pearl district, Portland features endless opportunities for travelers and foodies. Try several small dishes as you walk around Portland’s famed food truck blocks. Sample some of Portland’s best beers and sweet treats and take in other highlights like the International Rose Test Garden, Mt. Tabor Park, and Powell’s Bookstore.

  • Sip | Breakside, Ecliptic, Old Town, Zoiglhaus
  • Savor | Brunch: Screen Door or Tasty ‘n Alder,Lunch: Food Trucks,Dinner: Mediterranean Exploration Company or Lechon
  • Sleep | The Heathman Hotel

Day 2 | Columbia Gorge National Scenic Area & Hood River

Today, set out to explore two of the greatest attractions of the Pacific Northwest – the Columbia Gorge National Scenic Area and Oregon wines! Photograph the craggy ins-and-outs of the gorge while spotting for waterfalls and wildlife. Visit boutique wineries for sipping in the afternoon in the hamlet of Hood River, Oregon. Finish this full-day with a stop at historic Timberline Lodge on the slopes of Mt. Hood to take in the mountain’s splendor.

The Historic Columbia River Highway is home to abundant wildlife, picturesque towns, breathtaking vistas, and majestic waterfalls (including the second-tallest perennial waterfall in the United States: Multnomah Falls). See the landscape transform before your eyes as you travel from lush wet forests to high desert plains. Be on the lookout for Bald Eagles and Osprey, while admiring the towering basalt cliffs and other fascinating rock formations. On a clear day, white-cloaked volcanic peaks loom over us like sentinels guarding the majestic landscape.  Wander into a few nearby wineries to let the winemakers share the delicious story of the land; with each sip of wine you can begin to appreciate the terroir that can only be found in this secluded paradise.

Mt Hood is the highest point in Oregon, a dormant volcano, and the most climbed mountain in the US. The trip from Portland through the Columbia River Gorge and around Mt. Hood offers views of spectacular waterfalls, walks in pristine wine country, historic sites, and breathtaking mountain vistas.   No trip to the Mountain is complete without a visit to the historic Timberline Lodge, Oregon’s most treasured landmark.

  • Sip | Coffee: Stoked, Wine: Cathedral Ridge, Beer: Pfriem
  • Savor | Brunch: Broder Øst, Lunch: Solstice, Dinner: Celilo, Kin
  • SleepTimberline Lodge

Day 3 | The Willamette Valley

In the past decade Oregon has become a world-class wine state, with 15 approved wine growing regions (AVAs) and more than 300 wineries producing 72 varieties. The Willamette Valley delivers well-curated flavor but leaves pretense at the rustic, hand-hewn door. Taste at award-winning wineries and elegant eateries while marveling at the art of pairing local wines & farm-fresh foods. On the drive down, park your Subaru at Silver Falls State Park and lace up your walking shoes to head to any of several stunning water features.

  • Sip | Coffee: Live Local Cafe, Wine: St. Innocent, Coria Estates, Beer: Benedictine, Xicha
  • Savor | Subterra, Jory, Painted Lady, Bar Deux
  • Sleep | The Grand Hotel, Youngberg Hill Inn & Winery

Day 4 | The Oregon Coast

Considered to be one of the best coastal drives in the world, the Oregon coast twists and turns past picturesque lighthouses, charming beach communities, sea lion caves, and coastal monoliths like “Haystack Rock,” in Cannon Beach.  Forage for mushrooms, catch a crab, whale watch, hike or go tide-pooling; soak up nature in all its splendor along the celebrated Oregon Coast. Whatever you do, take a moment to feel the salt breeze on your face, hear the breakers crashing on the beaches and rocky shorelines, and enjoy the expansive views.  And don’t forget to take your shoes off to get your toes in the sand!

Peruse local shops, landmarks, and historic monuments before taking walks along the beach while spotting for abundant marine life and sea birds.

  • Sip | Coffee: Insomnia, Sleepy Monk, Beer: Whet Spot
  • Savor | Yolk, Salmonberry Saloon, Castaways, Una Ves Mas
  • Sleep | Commodore Hotel, Cannery Pier Hotel, Norblad (hostel)