Inspiration for your own tailor-made trip
Portland - Astoria - Depoe Bay - Bandon - Grants Pass - Prospect - Bend - Fossil - Hood River - Portland
100% customisable for you
Your epic adventure through the beautiful landscapes of lesser-visited Oregon starts today. Head to the airport, whizz through security and enjoy some refreshments in the airport lounge as you await the departure of your ten-hour flight to Portland.
On arrival, a private driver will be waiting to whisk you off to your first accommodation: a beautiful and bohemian hotel in the heart of the city, where you’ll be spend the next two nights.
The rest of this afternoon and evening are yours for the taking. Stuck on inspiration? Turn to our destination-specific Dossier, full of our top picks for bars and restaurants in the area, or simply kick back, relax and enjoy the hotel’s facilities after a busy day of travelling.
Stretching along the banks of the picturesque Willamette River, Portland is a green and trendy city that’s considered one of the nation’s most liveable (and loveable), thanks to its eclectic mix of parks, shops and residential districts.
Today, discover the downtown and Pearl District neighbourhoods in the company of a local guide who knows the city like the back of their hand. They’re also quite the culinary enthusiast, so expect to get stuck into local craft breweries and street food trucks (make sure to bring an appetite).
It’s time to bid farewell to the city and hit the road. After breakfast, collect your rental car and drive two hours west through pristine forested landscapes to Astoria, a historic city perched on the northwest coast. Your home here for the next two nights is an elegant contemporary hotel overlooking the Columbia River.
Once you’ve settled in and freshened up, head out to explore the city and its coastal surroundings. Visit the fascinating Columbia River Maritime Museum and tour Fort Clatsop, which once housed the famous American explorers Lewis and Clark. There’s also a collection of beautiful beaches within easy driving distance, so we recommend rounding off your day with a late afternoon stroll along the shoreline.
This morning, board the fully restored Arrow No.2, a vintage tugboat that made thousands of trips on the Columbia River from 1962 to 2012. It has become something of a legend in the region, thanks to its years of service supporting imposing boats and barges in their docking manoeuvres. This small group river cruise is a great way to soak in the region while learning about Astoria’s fascinating maritime history.
Once you’re back on dry land, you can continue exploring the city at your own leisure, or enjoy a private surfing lesson at Cannon Beach… the choice is yours.
Your Oregon road trip continues today with a three-hour drive south along the wild Pacific Coast to Depoe Bay, the smallest navigable port in the world. There are plenty of long, sandy beaches worth stopping at along the way, including Cannon Beach, Arch Cape and Nedona.
On arrival in Depoe Bay, check in for the night at an elegant and eco-oriented hotel overlooking the port and spend the rest of today exploring the beautiful town centre. If you fancy getting straight out on the water, we could also arrange for you to head out on a whale-watching adventure in a Zodiac.
After breakfast this morning, hop back into your hire car and continue south to your next destination: a beautiful hotel in Coos Bay. You’ll hug the coast for the entire three-hour journey, making it possible to break up the drive with some scenic stops. One of our favourite spots is Newport, a charming fishing town home to colonies of sea lions and the wooden Yaquina Bay lighthouse (the state’s last).
After settling into your hotel, spend the rest of today exploring southern Oregon. The region is known for its spectacular beaches and abundance of wildlife, including the elk at the Elk Preserve. It’s also well worth visiting the nearby town of Bandon, which specialises in crab fishing.
Today, bid farewell to the coast and head three hours inland to Grants Pass, a small western town near Rogue River. Everything here is geared towards outdoor activities, with hiking, fly fishing, kayaking and boat trips all available. If a visit to the famous Redwood National Park is on your USA bucket list, you could also switch up your route to make a detour to this splendid natural wonder.
On arrival in Grants Pass, check in for the night at a riverside wooden lodge and spend the rest of today enjoying the surrounding nature. This afternoon, we’ve arranged a rafting trip on Rogue River for you to admire the beauty of the steep cliffs, canyons and wildlife (including bald eagles).
This evening, we recommend enjoying the many delightful markets and eateries in the town centre before getting a good night’s rest.
Your road trip through Oregon’s landscapes continues today with an hour-and-a-half drive to Prospect, a small town located near the southern entrance of Crater Lake National Park. The journey there is oh-so scenic, passing through vineyards, forests, rivers and an increasingly mountainous landscape – and guess what? Your home for the night in Prospect is in the heart of it all.
After settling in and freshening up, enjoy the outdoor activities on offer, such as jet boating, whitewater rafting, fishing and wildlife watching.
Your next destination in Oregon is the small town of Bend, a paradise for outdoorsy adventurers, just a two-and-a-half-hour drive from Prospect. Not long after setting off, you’ll reach the serene (and surreal) Crater Lake National Park, a collapsed volcano filled with electric blue water. From here, continue to Bend and the comfortable hotel in the heart of town.
The rest of today and tomorrow are dedicated to outdoor fun. Enjoy rafting on the Deschutes River, or horse riding, cycling and hiking in Smith Rock State Park. We’ve also arranged a canoeing adventure on Cascade Lakes, a region loved for its peaceful, crystal-clear waters and spectacular views of the Three Sisters and Mount Bachelor.
After a hearty breakfast, hop back into your hire car and drive two hours northeast to a family ranch near Fossil. Along the way, make a stop at John Day Fossil Beds National Monument, a fascinating palaeontology site home to hundreds of fossils.
Once you’ve settled into the friendly ranch, spend this afternoon horse riding around the grounds in the company of the ranch owners (fear not, novices, it’s beginner-friendly).
The following day is yours to spend here at leisure. Kick back and relax in nature or step into the shoes of a palaeontologist with an archaeological dig in the aptly-named Fossil, the only town in the country where it’s possible to do so.
Today, bid a warm farewell to your lovely ranch hosts and continue your journey to the scenic city of Hood River, a three-hour drive from Fossil. This is a great opportunity to drive along a slice of the legendary Historic Columbia River Highway, a 75-mile highway that hugs the Columbia River Gorge from The Dalles to Troutdale. Your home for the night in Hood River is a historic and characterful hotel, located a stone’s throw from the city’s sights.
This afternoon, we recommend taking a little steam train to Mount Hood (the highest point in Oregon), where you can enjoy a gentle, picturesque stroll along forested trails.
After breakfast this morning, hop back into your hire car and join the US30 road back to Portland, an hour’s drive through beautiful vineyards and plantations. Along the way, make a stop in Cascade Locks, a small town home to the historic Bonneville Dam. The town is also a hotspot for salmon fishing, which you can experience with a paddle boat ride on the river.
Check in for one final night in a motel and spend the rest of today visiting any of Portland’s sights you missed at the start of your trip.
Sadly, the time has come to say goodbye to beautiful Oregon and embark on your journey home. After a relaxing morning, head back to the airport, drop off your hire car, whizz through security and enjoy some downtime in the airport lounge. Most direct flights back to the UK take around ten hours and depart in the evening, so you’ll spend tonight on board and touch down on home turf tomorrow morning.
Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
