Portland is known for being unique. Each neighborhood has an eclectic spirit of its own and there is plenty to explore. Visit the popular Japanese Garden, Washington Park or Forest Park, and work up an appetite to enjoy some of Portland’s fantastic restaurants or food trucks. Consider taking a food truck & food cart pod tour with Lost Plate Food Tours or a pub crawl with Throws Snakes Tours to uncover Portland’s weird and wonderful nightlife. Stay two nights in Portland. 

The Willamette Valley is known around the world for its Pinot Noir and a trip to this region of the state would not be complete without a wine-tasting tour. Dirty Radish offers behind-the-scenes tours of boutique wineries complete with experiences visitors would never have on their own. After exploring the idyllic rolling hills of vineyards, continue on to Eugene. If your trip is over a Saturday, be sure to stop at the Eugene Saturday Market, a vibrant marketplace of 150 local vendors displaying their handmade or home-grown products. Stay one night in Eugene. 

Continue your journey to the Oregon Coast where all 363 miles of coastline are free and open to the public. Due west from Eugene is Florence, home to the Oregon Dunes National Recreation Area. Explore the dunes via sandboard after receiving a lesson from an expert at Sand Master Park. Visit Heceta Head Lighthouse for spectacular views and the Sea Lion Caves for insights on marine life. Florence is also home to some delicious restaurants with seasonal, local menus. Stay two nights in Florence. 

Two hours south of Florence on the coast, you will find Port Orford, a small, artistic fishing town that is a true hidden gem on the Oregon Coast. Take a hiking tour with local guides to learn about native plants, animals, local lore, and history of this fascinating area. Venture out on the turquoise waters in this area via kayak, paddle board, or boat with South Coast Tours and you just may see a whale. Stay one night in Port Orford. 

From the Oregon Coast, you will head inland to beautiful Southern Oregon. On the way, stop at the Oregon Redwoods Trail to experience what its like to stand among ancient giants before journeying on. Grants Pass is the gateway to adventure on the wild and scenic Rogue River and a pillar of Southern Oregon wine country. Enjoy the different varietals of this region through a wine-tasting at Troon Vineyards, a biodynamic vineyard known for its regenerative practices, and Woolridge Creek Winery, Oregon’s first dual winery and creamery. Stay two nights in Grants Pass. 

Day 9 Grants Pass to Bend, approx. 190 miles 

Before you enter Central Oregon’s high desert, a must-see is Crater Lake National Park. The best way to experience the majesty of the seventh deepest lake in the world and learn about its history is with a guide. Main Street Tours will take you on a hike or snowshoe tour (depending on the time of year) to some of the best secret views in the park. Once in Bend, you’ll have access to world-class recreation experiences, award-winning restaurants, and boutique shopping (with no sales tax!). Wanderlust Tours offers unique, customizable experiences in the surrounding area, including dark sky, star-gazing tours. Stay two nights in Bend. 

North of Bend, you’ll find one of the natural wonders of Oregon, Smith Rock State Park. Known for its spectacular, rugged rock features and deep river valley, the park is a sight to behold, if only for a brief stop on your journey. As you continue towards Mt. Hood, you’ll pass through Warm Springs, home to the Confederated Tribes of Warm Springs. Littleleaf Guide Service offers the unique experience of fishing on 39 miles of Native land on the Deschutes River. From Warm Springs to Hood River, you will notice the landscape begin to shift from high desert to mountain forests. Set on the banks of the stunning Columbia River Gorge, Hood River is a charming town full of breweries, wineries and local shops. There are also plenty of opportunities to experience the landscape firsthand. Take a wine-tasting bike tour to discover the wineries of the Columbia Gorge with MountNbarreL. Stay two nights in Hood River. 

Follow the Columbia River as you head back to Portland. This area is known as the waterfall corridor and has plenty of opportunities to stretch your legs before dropping your car off at the airport in time to check-in for your flight home.