Portland and Beyond: 9-Day Adventure in Oregon Itinerary

Embark on a Portland Columbia River Gorge Waterfalls Morning Tour to witness the majestic Multnomah Falls and other natural wonders. Enjoy a picnic breakfast with a view.

Continue your gorge exploration with the Portland Columbia River Gorge Waterfalls Afternoon Tour. Later, visit the Vista House and then head to the Willamette Valley for an afternoon of wine tasting at local vineyards.

For dinner, experience the vibrant atmosphere and global cuisine at The Woodsman Tavern in the industrial Southeast Portland neighborhood.

Indulge in a morning of sweet treats on the Portland Downtown Coffee & Donut Tour. Sample some of the city's best coffee and donuts while learning about Portland's coffee culture.

Visit the Oregon Museum of Science and Industry (OMSI) for an interactive and educational experience. For lunch, enjoy the food and ambiance at Flying Elephants at Fox Tower.

Join the Portland Underground Shanghai Tunnel Tour with Beer Tasting for a unique blend of history and local brews. Afterward, if you're up for it, take the Portland Ghosts Boos and Booze Haunted Pub Crawl to uncover the city's spookier side.

Embark on a Portland Mt. Hood Day Tour to witness the stunning beauty of Mt. Hood. Enjoy breakfast with a view at Timberline Lodge, where "The Shining" was filmed.

Take a hike in the Mt. Hood National Forest to work up an appetite. Then, head to Rontoms for a casual and creative lunch in their outdoor seating area.

Relax and reflect on the day's adventures with a gourmet dinner at Expatriate, known for its fusion cuisine and intimate setting.

Start with a hearty breakfast at The Knock Back, a neighborhood bar with a great food menu. Then, join the City of Portland Tour Historic and Iconic Sights to learn about the city's history and iconic landmarks.

Enjoy a leisurely lunch cruise on the Portland 2-hour Lunch Cruise on the Willamette River. Take in the city skyline and waterfront views while dining on local cuisine.

For dinner, experience the global flavors and stylish ambiance of There Be Monsters. Afterward, take a relaxing Portland Willamette River 2.5-hour Dinner Cruise with live music and city lights.

Travel to the nearby city of Salem and start your day with a visit to the Oregon State Capitol. Afterward, enjoy a delightful breakfast at Library Taphouse & Kitchen.

Explore the Willamette Valley wine region with a guided tour, visiting some of the area's best wineries and vineyards. Pair your wines with a gourmet lunch at one of the stops.

Return to Portland and dine at Bar Maven, known for its craft cocktails and globally inspired small plates.

Start with a visit to the Pittock Mansion, a historic house with beautiful gardens and panoramic views of the city. Enjoy breakfast at Taylor Street Tavern, a local favorite with a laid-back atmosphere.

Spend your afternoon browsing the shelves at Powell’s City of Books, one of the largest independent bookstores in the world. For lunch, head to The Solo Club for a unique dining experience with global flavors and a curated wine list.

Dine at The Fireside, where you can enjoy a cozy and intimate meal with a focus on local and seasonal ingredients.

Travel to the city of Eugene and start your day with a visit to the Hendricks Park, known for its beautiful rhododendron garden. Enjoy breakfast at McMenamins Market Street Pub before continuing your morning explorations.

Explore the University of Oregon campus and the nearby Museum of Natural and Cultural History. For lunch, dine at Karam Restaurant and Bar, offering a blend of Mediterranean and Northwest cuisine.

Return to Portland and enjoy a relaxed dinner at Paddy's, an Irish pub with a warm and welcoming atmosphere.

Enjoy a final breakfast at Church Bar, known for its innovative cocktails and brunch menu. Spend your morning at leisure, perhaps visiting any favorite spots or doing some last-minute shopping.

For a memorable end to your trip, take a Bike Portland Bridges, Neighborhoods, Poetry, and Roses tour. Explore the city's bridges, vibrant neighborhoods, and hidden gems while learning about the local culture and history. Conclude with a late lunch at a spot that caught your eye during the ride.

Reflect on your Oregon journey over a farewell dinner at Virginia Cafe, a classic Portland establishment with a menu that pays homage to the region's culinary traditions. Raise a glass to the memories made and the adventures to come.