The Best of Oregon Fly Drive Holiday

16 nights

Oregon is perhaps one of the less well-known states in the US; unfairly so as it has so much to offer the holiday maker. From the sand dunes of the West Coast to the staggering Crater Lake and in between some delightful rolling countryside dotted with vineyards and farmland make for a splendid and relaxing fly-drive holiday. We have included a couple of the National Scenic Byways known throughout the States for their beauty and interest.


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The Breakdown

Here's a day-by-day guide to your itinerary. Feel free to ask us to add other days or ideas and excursions by adding them to your wishlist, so we can give you the best price.

Day 1

Portland & Willamette Valley

Fly from the UK (now on a direct flight from Heathrow) and arrive in Portland, the City of Roses.  The culturally rich downtown is surrounded by small, intriguing neighbourhoods, each with a unique flavour and heritage. Accolades have been dumped on Portland with the city dubbed the country’s best eating destination, America’s most sustainable city, one of the “greenest” cities in the world and more.

Settle into your downtown hotel in time to sample one of the cities restaurants before a well earned sleep.
2 nights in Portland

Day 2

Portland & Willamette Valley

Beginning your visit at the International Rose Test Garden will immediately immerse you in the visual beauty of Portland, which grows right out of the city’s history. Mrs. Pittock’s (wife of Portland magnate Henry Pittock) love of gardening introduced the tradition of displaying roses in 1888, leading to 20 miles of rose lined streets for the 1905 Lewis and Clark celebration. During World War I, the test garden received new hybrids rescued from destruction in the bombing. The Pittock Mansion, the product of Oregon craftsmen and artisans and Northwest materials, stands as a living memorial to these dedicated pioneers who spent nearly 60 years building Portland from a forest clearing to a bustling business centre with more than a quarter of a million people.

The Portland Art Museum, founded in 1892, is also a product of early Portland. An outstanding collection of American works is complemented with modern European masters. Visiting here puts you in the Pearl District, the old warehouse area— named to bring to mind an elegant gem nestled in a drab, rough shell. Be sure to explore the shops for high end jewellery. 

TIP - Buy a Portland Big Pass, you’ll be able to choose the additional attractions you want to visit in Portland. More of the story of lumbering in the Pacific Northwest is told at the World Forestry Center. The Oregon History Museum relates the story of the founding of the state, the Oregon Territory and the original Native American residents. The pass also includes the Oregon Zoo, and the Portland Children’s Museum. More truly delightful gardens await at the Lan Su Chinese Garden, Portland Japanese Garden, and the Hoyt Arboretum, 

Be sure to stop at one of Portland’s Food Carts, delivering unique foods, including the Colbert Super Mac with a half pound of beef, quarter pound of bacon, five slices of cheese, pickles, onions and lettuce, smothered in Freeberty sauce, all jammed between six slices of Texas Toast!

Consider taking a Portland Sightseeing Cruise for lunch or dinner to view the city from another perspective.



Day 3

Portland & Willamette Valley to Cannon Beach

Collect your hire car and leave Portland, you’ll be following the Columbia River to the dramatic yet serene beauty of the Pacific Coast Highway National Scenic Byway. Over the next few days, the natural wonders of the highway will unfold one after the other, with many attractions to visit and enjoy also integrally intertwined with the sea.

At the mouth of the river, Astoria was end of the Lewis and Clark 1803 Expedition to open the new continent for President Jefferson. The Astoria Column, which sits at the city’s highest point, is a celebration of the mission. The collection of the Columbia River Maritime Museum has grown to over 30,000 objects including the Lightship Columbia and other craft dramatically displayed in the museum. Enjoy a complete historical contrast at the 1885 Flavel House Museum and the replica of Lewis and Clark Fort Clatsop.

Before or after catching a bite of lunch at Dundee’s, you can experience marine life up close and personal at the Seaside Aquarium. Seaside itself has been a beach playground for the upper Northwest for more than 150 years. After serving as a fur trading post for more than a century, Seaside’s first guest house opened in 1850. When you reach Cannon Beach, Haystack Rocks and the ship cannons for which Cannon Beach is named, punctuate the landscape.

1 night in Cannon Beach

Day 4

Cannon Beach to Newport

Get an early start this morning; you won’t want to miss a single mile of the beauty along the coast.  The Oregon State Parks and Recreation Areas just keep coming: Arcadia Beach, Hang Point, Oswald West, Nehalem Bay, Manhattan Beach, Rockaway Beach. They are all great places to take plenty of photos. Stretch your legs at Garibaldi on the beach and at the Cheese Factory in the quaint town of Tillamook. For maximum scenery, be sure to take the Cape Mears Loop from Tillamook to Pacific City. When you reach Lincoln City, shop for exquisite glass creations at Jennifer Sears Glass Art Studio and have lunch at the Blackfish Café of the Culinary Center in Lincoln.

There will only be time for a quick dash through the Tanger Outlets in Lincoln City on your way to Newport, where you’ll soon discover everything marine. Nestled on beautiful Yaquina Bay, the Oregon Coast Aquarium is a world-class marine attraction, where, sealed in sparkling glass enclosures, fish, sea otters, harbour seals, California sea lions and other dramatic creatures swim overhead, under your feet and everywhere else. You can also take a 2-hour cruise whale watching tours. After a quick visit to explore the 93 foot Yaquina Head Lighthouse, finish out your day with famous seafood at Local Oceans and a night cap at the Rogue Ale Brewery.

1 night in Newport

Day 5

Newport to Gold Beach

Travel the Pacific Coast Highway National Scenic Byway on the Oregon Coast. Hear the roar of the great Stellar sea lions, the cries of wailing birds and the restless surge of the ocean into the cave below at the world’s largest Sea Lion Caves. The 25 million year old cave soars to the height of a 12 story building and stretches the length of a football field. Sea lions gather in the natural amphitheatre during fall and winter. In summer, they have their young on rock ledges just outside the cave. Just a few miles south, stay with the maritime theme with lunch at the ICM International C-Food Restaurant.

As you travel further south, the solitude of the Oregon Dunes National Recreation Area’s wind sculpted shifting sand dunes as high as 500 feet above sea level goes on for 40 miles. At Reedsport, you can detour to the Dean Creek Elk Viewing Area, where depending on the season, you will see Roosevelt Elk grazing, tussling, or running with their calves in a herd that has grown to as many as 100.  The antlers on the largest males can reach four feet. Coos Art Museum has special shows featuring maritime and coastal art.

Another hour on the coastal highway 101 will take you into Gold Beach where you can relax in your hotel situated on a wooded stretch of the Rogue River, just 7 miles from the Pacific Ocean.

2 nights in Gold Beach

Day 6

Gold Beach

Starting in Sunset Bay State Park, hikers can take a network of trails that connect the park with Shore Acres and Cape Arago State Park. Pristine coastal forests leave to spectacular ocean views from the headlands and rugged cliffs. The trees, shrubs and flowering plants of Shore Acres were once part of a private estate. Cape Arago, a scenic headland jutting into the Pacific was first spotted by Sir Francis Drake in the late 1500s. Consider a late breakfast or an early lunch at the Bandon Dunes Golf Resort just for the view.

The quaint coastal town of Bandon is authentic, historic and quaint. Old Town boasts galleries, boutiques, jewellery and other shops. Stroll on the beach or explore the Bandon Marsh National Wildlife Refuge. Colossal rocks jut straight up out of the Pacific Ocean in the Oregon Islands National Wildlife Refuge which spans 230 miles of Oregon coast including 1,853 rocks, reefs and islands in all.

TIP - board the Historic Mail Route boat  for a “Wild and Scenic” journey upriver

Day 7

Gold Beach to Ashland

It is time to leave the coast and head inland towards Crater Lake which is bound to be one of the high spots of your holiday.   On your way you might like to stop at Grants Pass for a rafting or jetboat trip through Hellgate Canyon. This is the stuff of movies, where John Wayne and Katherine Hepburn filmed Rooster Cogburn and Matt Dillon of Gunsmoke fame plunged into the depths of the water to escape a gang in hot pursuit.  You can either stay here or if you would rather stay in a town, you could carry on to Ashland.

The discovery of gold in 1851 brought Ashland in the form of Jacksonville, the original town, to life.  Besides gold, orchards blossomed and the city won top honours at the World’s Fair in 1893 for the Ashland peach. Ashland, known for its Shakespeare Festival, features a great group of galleries, housed in and nestled in between fine old Victorian homes. If you’re up for an afternoon winery tour, Southern Oregon has a collection of vineyards. Have dinner at the Standing Stone craft brewers before or after enjoying a night at the theatre.

1 night in Ashland

TIP - Take a break from the driving to have a 2,3 or 4-day rafting / hiking trip This can be a combination of camping and lodge based; whichever it will be a thrilling few days.

Day 8-9

Ashland to Crater Lake

No other place rivals the dramatic beauty of Crater Lake – deep, pure and astoundingly blue. America’s deepest lake descends nearly 2,000 feet into a caldera filled with some of the clearest water anywhere in the world. Not that long ago, Crater Lake was Mount Mazama positioned in the surrounding Cascade range, before it collapsed in violent volcanic explosions nearly 7,700 years ago, creating sheer cliffs nearly 2,000 feet high around the lake. The event is so recent that the story is still told in Native American legends. The Klamath Indians so revered the lake they kept it undiscovered until 1853 when three gold prospectors reached the summit to see the awe inspiring view. You can learn more the special qualities and features of the “Jewel of the Cascades,” by attending one of the Discovering Crater Lake Talks presented by park rangers daily.  Get out on the lake one of the daily boat tours accessible by hiking the Cleetwood Cove Trail, that take you to Wizard Island, which sits in the middle of Crater Lake. The island is a miniature cinder cone that supports a vast array of plant and animal life.  A two hour tour aboard the historic trolley navigates the 33 miles of the Rim Drive, making four stops along the way or if you would rather explore on foot, there are approximately ninety miles of hiking trails within the 180,000 acres of the park.

2 nights in Crater Lake

Day 10

Crater Lake to Bend

Between Oregon’s deepest and highest points, Crater Lake and Mount Hood, Paulina Peak juts out of the high desert in Central Oregon, surrounded by over 50,000 acres of Lava Lands. The Newberry National Volcanic Monument was created to provide a unique opportunity to view these lands, which are both seismically and geothermally active. Geologists believe that the 17 square mile caldera sits over a shallow magna body only two kilometres deep. Over 400 cinder cones are scattered throughout the area, among miles of basalt and obsidian flows. The summit area of Newberry Volcano holds two sparkling alpine lakes. There are a myriad of hiking trails within the Monument, many with interpretive material. Be sure to visit the Lava Lands Visitor Centre to learn more about the geology of this region.

You can join a tour to explore the hidden underground world of Central Oregon’s remote, desert lava caves with a naturalist guide. The three hour half day tour begins after lunch and concluding at 4:30 PM. The eruption that formed the Lava River Cave occurred about 80,000 years ago.

Enjoy a brew at the Deschutes Brewery or 10 Barrels Brewing company before or after dinner.

You can either stay in Bend or if you prefer to be in the countryside, we recommend the very comfortable Sun River Resort.

2 nights in Bend

Day 11


This morning, you can head out from Bend to the McKenzie Pass-Santiam Pass National Scenic Byway where the Cascade Mountains meet up with the Pacific Northwest’s “Ring of Fire” a series of volcanoes that created much of the geography of the region. First stop, 100 foot Sahalie Falls, where an easy 2.6 mile loop begins at the falls and descends past 70 foot Koosah Falls, returning along the McKenzie River Trail.

Nearby, the Dee Wright Observatory offers exceptional views of numerous Cascade peaks from the lava tube viewing holes of the lava stone viewing structure. Follow the Lava River Interpretive Trail through the lava beds. A stop in Sisters for lunch and some shopping brings you to the Old West of the 1880s. Galleries and boutiques abound in delightfully restored buildings.

Back in Bend, visit the High Desert Museum where outdoor exhibits at the museum continue the Old West theme you experience in Sisters, including the Lazinka Sawmill, the 1904 Miller Farm Ranch and more. Indoor exhibits illustrate how fur traders lived, the tribulations of travelling the Oregon Trail, and how early cowboys in the area spent their time. Relax later on the Bend Ale Trail, a trip through local microbreweries for those who enjoy a truly good brew.

Day 12

Bend to Baker City

Volcanic eruptions 44 million years ago sculpted the landscape on the route between Bend and Baker City today, known today as the John Day Fossil Beds National Monument. Five separate units: Sheep Rock, Painted Hills, Clarno, the Thomas Condon Paleontology Center and the James Cant Ranch Historic District are each distinct and each is worth a visit. The Sheep Rock unit features stunning geologic formations including Cathedral Rock and the blue-green volcanic ash of the Blue Basin has turned to claystone. This particular area has rendered a multitude of fossils.  The most prominent landform of the Clarno Unit is the Palisades, extraordinary examples of columnar basalt pillars. The Painted Hills features hillsides with layers of volcanic ash in a virtual artists palette. The Leaf Hill Trail passes through a 30 million year old fossilized forest. The James Cant pioneer ranch complex now serves as the headquarters of the John Day Fossil Beds National Monument as well as illustrating an early 20th century livestock ranch.

After exploring these wonderfully rich geologic formations, you’ll be on your way to Baker City, where the National Historic Oregon Trail Interpretive Centre features the story of the brave men and women who traversed the United States to settle the Oregon Territory. The location was the end of an arid trail segment where emigrants fought their way through shoulder high sagebrush having already endured four to five difficult days ascending Burnt River. Learn more of their story at the Baker Heritage Museum and the Adler House Museum. Geiser Grand Hotel, Baker City. Do visit Barley Brown’s Beer which has many award winning beers – a microbrewery where they are willing to take you on tours and discuss the beer-making process. 


1 night in Baker City

Day 13

Baker City to Wallowa Lake

Leaving Baker City this morning, you’ll be travelling the Hells Canyon Scenic Byway, a road with scenery so wonderful that it is designated one of only 31 All American Roads throughout the United States.  Your destination, Hells Canyon, the deepest canyon in North America, is 3,000 feet deeper than the Grand Canyon. Carved by the great Snake River, Devils Peak is more than 9,000 feet above the river.

You can take a jetboat into the deepest part of Hells Canyon to better experience the majestic scenery all around you. A stop to see the American pictographs and an early homestead, relates just how difficult canyon life was. The earliest date that can be proven that anyone occupied the canyon is 7,100 years ago, although there is evidence that life could have been present as early at 15,000 years ago. 

Shortly after you leave Oxbow, you’ll reach the Hells Canyon Overlook, where locals suggest “hang tight and look down!” It delivers a breathtaking view of the canyon. Further on, Wallowa Mountain and the Eagle Cap Wilderness has been called the “Switzerland of America.” After lunch in Joseph, you’ll be moving on to Wallowa Lake. Take the Wallowa Lake Tramway to the top of Mt. Howard for stunning views of the lake, the majestic peaks and the Seven Devils across Hells Canyon in Idaho.

1 night at Wallowa Lake

Day 14

Wallowa Lake to Pendleton

The remainder of Hells Canyon National Scenic Byway awaits this morning on your way to Pendleton. Begin exploring Pendleton at the Pendleton Round Up and Happy Canyon Hall of Fame. Exhibits which span 100 years of the world famous Pendleton Round Up include a full sized Teepee, Native American beadwork, saddles, clothing, Indian costumes, photographs, firearms, trophies, wagons and more. Now that you have toured the historic downtown, go underground with a tour guide to explore Hop Sing’s Chinese Laundry, the bordellos and other businesses connected by tunnels under Pendleton.  Native American culture comes alive at the Tamastslikt Cultural Institute Museum, illustrating the culture of people who have lived in the area for 10,000 years.

1 night in Pendleton

Day 15

Pendleton to Hood River

Soon after you leave Pendleton, your route will begin to parallel the Columbia River on your way into The Dalles and Hood River. Reaching The Dalles first, you’ll discover an authentic town alive with history, talking murals, historic sites, shopping, art glass and the Columbia Gorge Discovery Center.  During the Indian wars in the West, Fort Dalles was the only fort between Fort Vancouver and Fort Laramie, a vast distance between Canada and southern Wyoming. Contrast the Original Wasco County Courthouse and the Rorick House with the exquisite creations of Nicholas Art Glass to explore both faces of this interesting place.

Further on, you can visit a selection of unique Oregon wineries in Hood River, punctuated with galleries, clothing and jewellery boutiques and artisans shops. A side trip on the Mt. Hood Scenic Byway takes you to the foot of the highest peak in Oregon and the National Historic Landmark Timberline Lodge. Leaving Timberline, the Fruit Loop takes you through Columbia valley’s orchard growing region, especially abundant with pears which are grown, harvested and sold as both fresh fruit and wine.


2 nights in Hood River

Day 16

Hood River

Explore Mt. Hood, Hood River, Multnomah Falls, Mt. St. Helens and much more. There is so much to discover in this corner of the Pacific Northwest: golf courses, hot springs, wineries, rafting, biking, boating, three volcanic mountains, the quaint towns of Hood River, OR and Stevenson, WA that you might just want to spend an extra day.

Day 17

Hood River to Portland & Willamette Valley

It is only an hour to the airport so you will still have plenty of time to wander along the Columbia Gorge.  

TIP: Do take the slower Historic Columbia River State Trail along the south shore: the scenery is stunning. 

A last drive along the Columbia River will bring you back to Portland where you will drop your car at the airport and fly back to the UK.

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The View

A selection of images representing the areas and places you will be visiting to give you a glimpse of what lies in store during your holiday.

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