Plan on spending 2 weeks in Oregon and you'll get a much better sense of this state's diverse landscapes. You'll also get to spend more time exploring the great outdoors and taking interesting tours.
Days 1 & 2: Portland
Start your Oregon vacation in Portland, where parks and gardens are the main attractions. Downtown, stroll through Tom McCall Waterfront Park, ride the Portland Aerial Tram, and visit the Portland Classical Chinese Garden. In Washington Park, visit the Japanese Garden and the International Rose Test Garden. If you're the outdoorsy type, go for a hike in Forest Park or paddle the Willamette River in a sea kayak. Alternatively, do a jet-boat tour with Willamette Jetboat Excursions. Go shopping in the Pearl District or on Nob Hill, and check out the Portland Art Museum. Spend some time in a brewpub, wine bar, or cafe.
Days 3 & 4: The Mount Hood Loop
Spend the next 2 days circling snow-covered Mount Hood by way of the Columbia River Gorge. Drive the Historic Columbia River Highway and stop at Multnomah Falls and other waterfalls. Hike the Eagle Creek Trail, and then relax on a river cruise aboard the stern-wheeler Columbia Gorge. As you loop around snowcapped Mount Hood, Oregon's tallest peak, stop in Hood River or at the historic Timberline Lodge for the night. Go for a hike, perhaps at Cooper Spur, on the northwest side of Mount Hood.
Days 5 & 6: Bend
From Mount Hood, head south into central Oregon's high desert and ponderosa-pine landscapes. This region gets more sunshine than the west side of the Cascades and consequently has several golf resorts. Near the town of Bend, you can explore the lava fields, cinder cones, and volcanic crater of Newberry National Volcanic Monument; go white-water rafting; and hike beneath the jagged peaks of the Three Sisters. In winter, go skiing or snowboarding at Mount Bachelor.
Day 7: Crater Lake National Park
Continue south from the Bend area to Crater Lake National Park, which preserves the deepest lake in the United States. Drive the scenic road around the lake and take a boat tour. Do one or two short hikes to high points along the rim of the caldera that forms this gorgeous blue lake. Stay at Crater Lake Lodge.
Days 8 & 9: Ashland & Jacksonville
If you're a fan of Shakespeare or the theater in general, you'll want to spend a couple of days in the hip retirement town of Ashland, where the Oregon Shakespeare Festival stages the Bard's works from February to October. Plenty of other playwrights also get equal time. When you aren't at the theater, shop the great boutiques, do a little wine touring, and eat out at the best restaurants in southern Oregon. Drive over to the historic town of Jacksonville, which is also home to the Britt Festivals, a summer-long series that brings in great musicians and dance troupes.
Days 10 & 11: The Southern Oregon Coast
From Ashland, head to the southern Oregon coast (the highway will take you briefly into the redwood country of northern California). The most scenic stretch of the coast is between Brookings and Gold Beach. Most of this area is preserved as the Samuel H. Boardman State Scenic Corridor, which has lots of overlooks and also includes many stretches of the Oregon Coast Trail. In Gold Beach, take a jet-boat tour up the Rogue River. Spend a night in Bandon, where the beach is littered with monolithic haystack rocks.
Day 12: The Central Coast
North of Bandon, a trio of state parks--Cape Arago, Sunset Bay, and Shore Acres--should not be missed. These three parks are all within a few miles of each other and you can easily visit all three in a few hours. North of Coos Bay, you drive through the Oregon Dunes National Recreation Area, where some sand dunes are 500 feet tall. There are lots of hiking trails through the Sahara-like landscape. Stop for lunch in the historic river town of Florence. North of Florence, the mountains once again meet the sea. Stop at Sea Lion Caves and the picturesque Heceta Head Lighthouse before exploring the rugged shoreline of Cape Perpetua Scenic Area. Stay in Yachats.
Day 13: The Three Capes Loop
From Yachats, drive north to Newport and visit the Oregon Coast Aquarium. Then work your way through the traffic congestion of Lincoln City to reach the little fishing town of Pacific City, and the start of the Three Capes Scenic Loop. Climb the giant sand dune at Cape Kiwanda State Park, then drive north to Cape Lookout State Park and, if you have time, hike out to the end of the cape. The last stop on this loop is Cape Meares State Park.
Day 14: Astoria
Continue north, stopping in Manzanita and artsy Cannon Beach to see two of my favorite Oregon coast towns. Also be sure to take the short hike to the beach at Oswald West State Park. Finish your tour in Astoria, a working port town with lots of grand old Victorian homes. Just outside of town, you'll find Lewis and Clark National Historical Park, which commemorates the explorers who spent the winter of 1805-06 here at the mouth of the Columbia River. The next day, head back to Portland.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.