Itinerary

America’s leafy metropolis, Portland is famous for its incredible parks, endless bike paths and verdant scenery, as well as its eco-friendliness, craft beer culture and delicious food carts. With so much to explore, spend the day taking in Portland’s key sights after checking in to one of Portland’s finest historic hotels, The Benson.

Start by hopping on the Portland Aerial Tram. The 4-minute-long journey takes you 152m up over the city so you can take in all that Portland has to offer. Then, a visit to one of Portland’s many green spaces is a must. Stroll through the stunning Japanese Gardens in Washington Park – you’ll find cherry blossoms, koi ponds and even a traditional tea house – or take advantage of the hiking and mountain biking opportunities in Forest Park.

For a taste of urban living, head over to Portland’s Pearl District brimming with art galleries, independent shops, boutiques and farm-to-table fine dining, or get a taste of Portland’s innovative food scene with a guided tasting tour of its food carts.

Start your day exploring the breathtaking beauty of one of the most picturesque places in Oregon with a guided half-day tour of Multnomah Falls and the Columbia River Gorge. Created millions of years ago during the formation of the Cascade Mountain Range, the narrative of this spectacular landscape and its transformative history will be introduced to you by an enthusiastic and knowledgeable local guide as you walk through these amazing locations.

Spend the rest of your day visiting whatever you didn’t get to see the previous day before finishing off your time in the city with a visit to Distillery Row. With over 500 homegrown craft breweries, a tasting is well worth your time.

Pick up your rental car after breakfast and make the 45 minute drive over to the heart of Oregon’s Wine Country: Dayton in Willamette Valley. A charming town with rich pioneer history, you’ll find no less than 41 places in Dayton are listed on the National Historic Registry, including the historic town square park in downtown Dayton where its residents and businesses congregate. Arrive at the one of a kind Vintages Trailer Resort and get settled in before heading out for some wine tasting.

Willamette Valley is one of the world’s premier wine regions, home to around 700 wineries, and is renowned for its Pinot Noir and farm-to-table dining. Willamette Valley is also filled with agriculture, so you can visit local farms, meet the growers, walk their fields and pick a basket of fresh produce to take back to your hotel.

Wine tasting isn’t all there is to do in Willamette Valley and for those who like to explore, there are plenty of outdoor opportunities. Cycle between vineyards along the picturesque Willamette Valley Scenic Bikeway, or stop and smell the wildflowers, count the birds and spot butterflies as you hike through the lush landscape – the area is ideal for peaceful contemplation.

After breakfast drive to the seaside town and working harbour of Newport right on Oregon’s central coast. You’ll be staying in a hotel on a bluff overlooking the Pacific Ocean, so get settled in and acquainted with the spectacular views. Newport is home to one of Oregon’s oldest lighthouses, Yaquina Head, and boasts the breathtaking beauty of the Yaquina Head Marine Garden, so spend the day discovering the unique maritime history of the area with a guided tour of the Yaquina Head Lighthouse, or explore the stunning shores, living tide pools and rugged oceanside cliffs at your leisure. End the day with a bowl of freshly made chowder before heading back to your hotel to look out on the beautiful blue ocean by a fire – there’s no better way to wind down and relax.

Start the morning with a walk along one of the hiking trails in South Beach State Park. You’ll be treated to amazing views of unspoiled coastal scenery, not to mention a beautiful environment in which to take a contemplative walk. Alternatively, take a whale watching tour from one of the city’s local operators. Newport is an excellent location from which to spot the local marine life.

Spend the afternoon strolling the charming historic district of Nye Beach. The little boutique shops and art galleries lining the streets are fun to visit and if you’re looking for a bite to eat for lunch or dinner, you’ll find plenty of delicious options in the district’s eateries. Come sunset head down to the beach itself and stroll along the picturesque shores and crystal clear waters while watching the sun set. You’ll find you can’t get a more relaxed setting.

Drive first thing in the morning down to the small and charming town of Bandon. You’ll have a scenic 2.5-hour road trip along Highway 101 to one of the Oregon Coast’s most popular destinations, located at the mouth of the winding Coquille River, right where it empties into the Pacific Ocean. Boasting a historic Old Town filled that dates back to the founding of the city in the late 1800s, Bandon offers innumerable opportunities for outdoor recreation across its coastline, river and forest. View beautiful rock formations, go hiking and watch wildlife, or stroll the streets of the Old Town for local boutiques and delectable dining.

The Oregon Islands National Wildlife Refuge is well worth a visit after you drop off your bags, and a walk to the Face Rock State Scenic Viewpoint or the Coquille River Lighthouse is equally enticing leading you past white-tipped waves, broad sand beaches, life-sized rocks and lively tide pools.

After breakfast, make your way over to the historic town and pillar of the southern Oregon wine country, Grants Pass. Known for its outdoor recreation, fine wine and historic charm Grants Pass is a picturesque place to spend the next two nights.

You’ll be arriving at The Lodge at Riverside, located right on the scenic Rogue River in the heart of downtown. Start with a stroll through the town’s National Historic District to view the classic 19th-century homes and commercial buildings, stopping to browse the impressive collection of antique stores and the lovingly restored Historic Rogue Theatre. Make sure to also stop by The Glass Forge in the downtown to watch artisans work in this fully operational glass blowing shop.

If you still have time after your walk, squeeze in a visit to a winery or two – Schmidt Family Vineyards and Woolridge Creek Winery come highly recommended and the region specialises in big reds and classic whites, so you’ll have plenty of delightful varietals to try.

Grants Pass sits on the lively Rogue River and the location offers adventures to suit all types. Spend the day hiking your way along the stunning 40-mile Rogue River Trail or rent a raft or kayak to cruise along the Rogue National Wild and Scenic River. This 33-mile section offers the trip of a lifetime, and you’ll find various tour operators offering excursions here as well, so you won’t have to go out on your own. A jetboat ride through the dramatic scenery of Hellgate Canyon is also worth your while if you’re feeling adventurous.

Drive first thing in the morning to the town of Prospect, just 20 minutes from the astounding natural beauty of Crater Lake National Park. The deepest lake in the United States, Crater Lake occupies the remains of a vast volcanic caldera – formed by the collapse of Mount Mazama some 7,700 years ago – and is noted for its exceptional clarity, intense, sapphire-blue colour and breathtaking alpine surroundings.

Arrive after an hour’s drive at the beautiful Prospect Historic Hotel and drop your bags off before delving into the depths of Crater Lake. Start with a drive on the 33-mile long road around the lake, called Rim Drive, to get dramatic views and numerous viewpoints for photo opportunities. After all that driving chances are you’ll want to get out of the car so take a short hike through the breathtaking alpine surroundings or sail across Crater Lake’s pristine waters with a boat tour. Doing the latter guarantees a stop on Wizard Island, the lush volcanic cinder cone that rises out of the lake.

End your time here with a sunset dinner at Crater Lake Lodge, where you’ll find a well-deserved and delicious meal with stunning views to match.

After breakfast drive 2.5 hours up to one of Oregon’s most charming small towns, Sisters. Offering one of the best locations in the state for scenic drives, hiking and relaxing walks, Sisters is also known for its unique Old West ambiance, well-preserved 19th-century facades and thriving creative arts community.

Get settled in to your stunning 20-acre property and plan your day from there. Your hotel offers excellent amenities, and the scenic Aspen Lakes Golf Course is just a short drive away should you want to take it easy. For those eager to get outdoors, start with a bike ride to explore downtown and the surrounding areas. The Peterson Ridge Trail in the southern part of the city is a local favourite and even offers hiking trails for all levels.

Spend the day getting to know Sisters with a walk through the Indian Ford Meadow Preserve. This peaceful nature walk offers excellent views of the Cascade Mountains. Another option is to drive to the nearby Sahalie and Koosah Falls or Proxy Falls. These ethereal waterfalls are nestled in lush surroundings perfect for a morning hike.

Take the late afternoon to shop for fun souvenirs in Sisters Old West downtown district – you’ll find everything from trinkets and handmade crafts to antiques and modern art – and you won’t want to leave without experiencing Sisters’ pioneer town ambiance.

Leave first thing for Fossil – you’ll want to start your time here sooner rather than later. An endearing small town once part of the famed Oregon Trail, Fossil is famed for having some of the world’s most impressive fossil specimens, and being one of the few places in the world you can legally dig for fossils. You’ll be arriving at the Wilson Ranches Retreat, an authentic 9,000 acre Oregon ranch with awe-inspiring scenery and rustic home comforts.

Sign up for a scenic horseback ride to enjoy world-class views journeying through the Columbia River Plateau and John Day Basin – you won’t get a more authentic ranching experience than this – or head down to the pristine beauty of the second longest free-flowing river in the United States, the John Day River, for swimming, floating and world-class fishing holes.

Fossil is located right next to the world-renowned John Day Fossil Beds National Monument, and if you only decide to do one thing, make it this. The colourful rock formations inspire awe, and the local ecosystems and fossil beds span over 40 million years of prehistoric history.

Make the 2-hour drive over to the historic town at the base of Mount Hood, Hood River. If you can spare an extra half hour or so in the car make sure to go along the spectacular Journey Through Time Scenic Byway on your way there. You’ll encounter breathtaking natural beauty, Old West culture and haunting ghost towns worthy of a picture.

When you finally arrive at the base of Mount Hood, the 4th highest peak of the Cascade Mountains that towers 11,239 feet over the Hood River Valley you’ll find a friendly town that plays host to an eclectic mix of restaurants, shops and galleries. The area is a haven for outdoor enthusiasts – go mountain biking along the many trails in the Post Canyon Trail System or windsurfing in the cool, clear waves of the Columbia River; hike the countless forest paths or, for serious backpackers, cross from Mount Hood onto the world-famous Pacific Crest Trail; go paddleboarding on Trillium Lake or watch the sun set and reflect Mount Hood in its shimmering waters. You’ll be staying at the centrally-located, historically-noted Hood River Hotel, so getting around will be easy.

If you have time before you leave, the area also boasts a bountiful fruit industry which can be enjoyed from the scenic 35-mile drive known as the Hood River County Fruit Loop. Taking you through the valley’s orchards, forests, farm stands, cider makers and vintners, who work all year long to bring a taste of the Hood River Valley to visitors from around the world, it’s a sweet finish to an even sweeter stay, and a little bit of Oregon you can take on your homeward journey. Drop off your rental car before leaving and take your flight home from PDX.