Day 1 - Fly from the UK to Portland
Known for its friendly, open-minded spirit, creativity and sustainability, Portland is an exciting and vibrant city to discover. Explore on foot, by bike or take a paddle on the Willamette River which runs through the heart of the city.
Stay three nights in Portland.
Day 4 - Portland to Newberg, approx. 45 miles.
Immerse yourself Oregon’s wine culture today as you head into the Willamette Valley. Known specifically for its Pinots, you can visit numerous wineries and tasting rooms in and around Newberg to sample some of the region’s best wines, whilst taking in the stunning views of the Cascade Mountains.
Stay one night in Newberg.
Day 5 - Newberg to Pacific City, approx. 150 miles
It’s not the most direct drive today, but it will definitely show you some wonderful Pacific Coast vistas. At Ecola State Park you can stroll or hike through Sitka forest and along cliffside trails, or just sit at a bench and watch the waves rolling in.
Stay one night in Pacific City.
Day 6 - Pacific City to Newport, approx. 45 miles.
Your first stop today should be Yaquina Head Lighthouse. Yaquina Head Lighthouse's 93 foot tower, Oregon's tallest, is located on a narrow point of land jutting west into the Pacific Ocean north of Newport, at Yaquina Head Outstanding Natural Area.
Stay two nights in Newport.
Day 8 - Newport to Bandon, approx. 120 miles.
Stop and hike at Cape Perpetua, a typical Pacific Northwest headland, forming a high steep bluff above the ocean. At its highest point, Cape Perpetua rises to over 800 feet above sea level. From its crest, you can see 70 miles of Oregon coastline and as far as 37 miles out to sea on a clear day. Take a tour of Heceta Head Lighthouse or experience the Sea Lion Caves on the coast near Florence, one of the largest sea caves filled with Oregon’s Stellar Sea Lions.
Stay one night in Bandon.
Day 9 - Bandon to Jacksonville, approx. 160 miles
Head inland today and into some more beautiful wine and fruit producing countryside. Travel through the Umpqua Valley and south to the Rogue and Applegate Valleys. There are plenty of small towns to stop in, including your destination, Jacksonville, a historic Gold Rush town now known for a thriving cultural and epicurean scene. Named one of America’s top 10 coolest small towns by Budget Travel Magazine, Jacksonville is home to the summer-long Britt Music & Arts Festival, an incredible selection of independently owned shops and eateries, celebrated winemakers and great hiking and biking opportunities. You’ll also find golf, horse-riding and water adventures on the Rogue River.
Stay two nights in Jacksonville.
Day 11 - Jacksonville to Sisters, approx. 200 milesYour highlight today is bound to be Crater Lake National Park which has inspired people for hundreds of years. No place else on earth combines a deep, pure lake, so blue in colour; sheer surrounding cliffs, almost two thousand feet high; two picturesque islands; and a violent volcanic past.
Spend two nights in Sisters.
Day 13 - Sisters to Hood River, approx. 145 miles
Make a stop at Smith Rock State Park, generally considered the birthplace of modern American sport climbing and is host to cutting-edge climbing routes. Smith Rock also offers miles of hiking and mountain biking trails. Whether you come for the climb or come to unwind, you’ll see why Smith Rock is one of the 7 Wonders of Oregon.
Stay two nights in Hood River.
Day 15 - Hood River to Portland, approx. 60 miles.Head back to the airport along the Old Columbia River Highway. The Columbia River Gorge National Scenic Area offers 292,500 acres of unparalleled scenery and outdoor recreation options. A leisurely drive on the Historic Columbia River Highway is a popular way to experience the gorge. Return your car to the airport in time to check-in for your flight home.
Posted by: America As You Like It
Posted on: 01/01/2026