Go Road Tripping
Drive the stunning winding roads of the Vineyard and Valley Scenic Byway.
This journey by road through the lesser-visited Pacific Northwest state of Oregon encompasses miles of coastal roads, expansive wine valleys and an iconic National Park that boasts the deepest lake in the United States.
Whether staying in a cabin on the Rogue River, watching the sunset on Cannon Beach or sipping wine in a rolling valley, this journey has something for everyone.
Drive the stunning winding roads of the Vineyard and Valley Scenic Byway.
Paddle in the crystal-clear waters of Crater Lake, surrounded by evergreen forests
Discover the quirky city of Portland, with its many eateries and coffee shops.
Spend time ambling along sandy Cannon Beach on the dazzling Oregon coast.
Uncover the highlights of the Pacific Northwest while travelling between dramatic valleys and thrilling cities, sipping sun-downers on sun-drenched beaches and tasting your way around vibrant markets. Encompassing the real focal points of Oregon, this classic journey through the land of award-winning grape-growing regions and the homeland of black bears and coyotes is one of extremes. From the Cascade Mountain-flanked town of Bend to the stream-laden walks of the Columbia River Gorge, this trip takes in fascinating landscapes, vibrant streets and pristine coastlines. The addition of a long coastal drive to the world-renowned Cannon Beach, a journey that takes a little under seven hours, makes this a highly customisable bucket-list-worthy adventure to the colloquially named “Beaver State”.
Spend time in the foodie hotspot of Portland, the largest city in Oregon but a place that still maintains the charm of a small town, from where you will head out on private guided tours of the Willamette Valley, the Columbia Gorge Waterfalls and Mount Hood. Award-winning cocktail bars and peculiar coffee establishments line the vivacious streets, while miles of hiking trails and kayaking routes await less than an hour outside of the city. Experience tastings at three carefully selected vineyards, learning all about the history of wine production in Oregon from your expert guide and hearing stories about the local area.
The combination of stunning mountains, evergreen forests and deep lakes makes Crater Lake National Park a diverse destination that doubles as a habitat for all sorts of wildlife that includes hummingbirds, black bears, coyotes and chipmunks. At 7,700-year-old, the crystal-clear Crater Lake is the deepest lake in the United States and was formed during the volcanic collapse of Mount Mazama. During the milder months, when the landscape is verdant green, paddle in the waters of the sapphire-blue lake to cool off after a day of hiking underneath the sun. In winter, the landscape is coated in lashings of pristine snow, making this a dream destination for ranger-guided snowshoeing.
Travel to Rogue River, perhaps staying in a riverside wooden cabin frequented by none other than Walt Disney himself. Toast marshmallows on an open fire, spend a lazy afternoon with your feet in the cool river perusing a good book, or go river-side cycling. During your time in this traditional and unpretentious region of Oregon, absorb the country charm and head out on a day of discovery with a wine-country picnic in tow. You might like to visit some of the many old-fashioned general stores, thought of as community hubs, to sample their trademark grilled sandwiches or craft beers.
Featuring one of the most notable landscapes in the Pacific Northwest, Cannon Beach is the highlight of the Oregon coastline and globally renowned as one of the world’s most scenic destinations. This small coastal town, with its long, sandy shoreline, is a creative and diverse spot with dozens of art galleries, restaurants and boutique shops. Peruse local shops, landmarks and the town’s historic monuments or visit the beautiful state parks up and down the shoreline. The iconic monolith of Haystack Rock that frames the coastline is a particular point of interest for keen photographers, while keen wildlife and nature enthusiasts will love to walk through the coastal rain forests to spot some of its seabirds.
Below you can see some of the wonderful places we have recommended for this journey.
Benefiting from an impressive waterside vantage point, Alderbrook Resort & Spa is a contemporary resort built in a traditional wooden chalet-style and sits against a backdrop of the thriving forest.
Born from a genuine love of the land, Brasada Ranch is a 1,800-acre resort in central Oregon that looks out on to breath-taking, uninterrupted and panoramic views of the Cascade Mountains. Its intimate, boutique-style rooms have been decorated in harmony with the surrounding nature, and some include private firepits and hot tubs.
Possessing the warmth and hospitality of a bygone time, Crater Lake Lodge enjoys majestic views of the lake from its site in the Rim Village Historic District. A base for hiking and swimming next to the sapphire blue lake, Crater Lake Lodge is a cost property constructed with timber features throughout, roaring fireplaces, warm coloured rugs and patterned fabrics.
Positioned on downtown Seattle’s University Street, the Fairmont Olympic Hotel is a lavish and opulent retreat that encapsulates the old-world charm of the Italian Renaissance. The property showcases 450 spacious and comfortable rooms and suites that are decorated with traditional period furnishings.
Set on the picturesque Friday Harbour on the east of San Juan Island, Friday Harbour House is an intimate coastal retreat that offers just 24 newly updated rooms.
Set at the renowned Pike Place Market in downtown Seattle, Inn at the Market offers a tranquil hideaway from the vibrant metropolis of the Seattle Waterfront outside. The property features 70 well-appointed and elegant rooms, overlooks the Olympic Mountains and the Puget Sound and features a panoramic rooftop deck.
A lakeside getaway on the banks of the spectacular Columbia River, the authentic Skamania Lodge offers its guests a markedly Pacific North-western experience. Showcasing a magnificent three-story stone fireplace, extensive river views, two locally-inspired restaurants, a golf course and a spa, the lodge is nestled within 175 wooded acres. Its 254 humbly decorated rooms and suites offer a range of views that include the woodland, lake, Columbia River Gorge and the Cascade Mountains, while the hidden treehouses welcome absorbing views from their location within the fir tree forest. There is an on-site spa and fitness centre, a selection of restaurants and a challenging 18-hole lodge-owned golf course that is shrouded in the acres of woodland.
Set on Oregon’s scenic north coast in the quiet region of Cannon Beach, Stephanie Inn overlooks the Pacific Ocean and the iconic monolithic of Haystack Rock. With just 41 guest rooms, Stephanie Inn makes the most of the surroundings with balconies on every floor that encourage guests to relax in the breeze. The interior has a purposeful elegance with east coast influences of heritage style furniture and deep colours throughout, and this cosy atmosphere is bolstered by the use of fireplaces in each room for use during the cooler months. The intimate in-house restaurant serves a menu of organic produce complemented by fresh fish and local meats. Awarded as one of Travel+Leisure’s World’s Best Hotels, it remains one of the leading properties in this region.
Established on 35 acres of hillside within the fertile Willamette Valley, The Allison Inn & Spa offers an indulgent resort experience in the heart of Oregon’s famed wine country. The drive up to the main property itself cuts through 7 acres of estate vineyards, revealing the impressive and inviting 85 room lodging that is interspersed with balconies, terraces, spa-like bathrooms and lavish amenities.
Situated in the heart of downtown Portland, The Heathman Hotel is a historic and coveted property that is considered to be one of the city’s most iconic landmarks. Melding its rich history with a contemporary admiration for the arts, the property oozes creativity and offers a retreat from the effervescent city outside.
Located in lively downtown Portland, The Nines is a contemporary and stylish property that exhibits art-filled spaces, inspired dining and fantastic views. The hotel has 331 sumptuous rooms that are decorated with an artistic flair and attention to trendy details. The property is of particular architectural interest, being set within the now non-existent historic Meier & Frank building, a once major Portland department store.
Overlooking the iconic Pacific Northwest seascape of Cannon Beach, The Ocean Lodge has a relaxed and charming atmosphere and feature comfortable rooms overlooking the Pacific coastline. Just steps from the vast sweeping beach, ocean-facing rooms offer panoramic views across the shoreline and towards the iconic Haystack Rock. The lodge has an intimate feel, with just 37 comfortable rooms in the main building and a further 8 set back from the central property.
Snuggled within the cosmopolitan mountain municipality of Bend in Oregon, The Oxford Hotel is an eco-boutique property that serves as a comfortable base from which to discover the many activities on offer in the region. The 59 well-appointed and ambient rooms fuse organic aesthetics with sustainable high-end amenities and are decorated in relaxing natural shades of white, grey and chocolate brown. The property boasts a spa with a jacuzzi, sauna and steam room, as well as a fitness centre and complimentary use of bicycles. The on-site restaurant 10Below showcases urban, organic and locally-sourced dishes that can be enjoyed in the restaurant or the comfort of your room.
Constructed from timber in a traditional lodge style, sheltered on all sides by tall trees, Weasku Inn is a tranquil hideaway in the wine-producing Applegate Valley. Offering a selection of cabins, lodge rooms and Jacuzzi suites along the notorious Rogue River, Weasku Inn is a charming accommodation that once served as a retreat for world-renowned entrepreneur and film producer Walt Disney. There are five rooms in the main lodge, eleven cabins in the grounds and an original A-frame cabin, each upholding the character and splendour that has earned Weasku Inn its title of one of Travel+Leisure’s Top 25 Lodges.
All the way through the process - from us explaining what we wanted through to the programme that Roxy created - everything was excellent. Roxy understood our requirements perfectly and created a trip that exactly fitted the bill.
From my first conversation with Roxy, it was clear that her knowledge was very good indeed. She listened to our ideas and created a fantastic bespoke holiday for us, and the pre-trip information was first class.
Our experts have created and curated these tailor-made holiday ideas to get you started. Take the time to search through them and find something that is the spark for your unique adventure.