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Oregon Fly-Drive

12-day tailor-made self-drive from £2,340 pp incl. flights


Short description

A luxury Oregon road trip taking in the spectacular landscapes of America's Pacific Northwest


  • Explore Portland's artsy intrigue
  • Take in the dramatic beauty of Crater Lake National Park
  • Taste Newport's world-class wines
  • Ride a buggy through the Oregon Dunes NRA
  • End with Sunriver – a region of outstanding natural beauty

In Brief

  • 2 Nights Portland
  • 2 Nights Newport
  • 1 Night Florence
  • 2 Nights Grants Pass
  • 2 Nights Sunriver
  • 1 Night Portland


Recommended for:
History & culture | Natural world | Self-drive

This curated itinerary showcases the best of Oregon's myriad highlights. You'll begin with a city great, taking in Portland's thriving arts and dining scene before heading out to Newport – the heart of Oregon Wine Country. Indeed, as throughout your trip, you'll be treated to gorgeous drives along scenic byways, characterised by historic lighthouses, sleepy fishing villages and enormous views of the Pacific Ocean views. Keep your eyes peeled for whales and sea lions. Then, moving away from the coast and the great sand dunes, you'll head into the mountains for gaint peaks, spruce forests and the wonders of Crater Lake National Park. It's a perfect mix of natural beauty and small-town charm.

Day by day itinerary

Days 1-2

After making the most of your complimentary airport lounge access, catch your day flight to Portland. You'll pick up your hire car on arrival for the short drive to your accommodation – a 1931 landmark hotel in the city's centre. You'll quickly discover Portland's famous cuisine, vibrant arts scene and funky shopping districts, wrapped up in intriguing neighbourhoods. Each has its own unique flavour, from artsy Peal District and Nob Hill's boutiques to Old Town Chinatown's infectious buzz. It's home to the famous Portland Saturday Market, Voodoo Doughnut and Lan Su Chinese Garden. Don't also miss out on the effortlessly hip Mississippi Avenue.

Stay: The Benson, Portland (Superior)

Days 3-4

Today, you will travel through the heart of Oregon Wine Country, passing over 100 wineries on scenic byway, alongside sleepy fishing villages and amazing coastal vistas. Depoe Bay's Pacific-Ocean views and Lincoln City's seven miles of beach are particular highlights. You'll then arrive in Newport to stay at one of its most impressive properties, where the private balconies of your traditional room invite in gorgeous ocean views. The complimentary homemade cookies are a nice touch. From here, you'll be perfectly poised to explore Newport's delights, from beach walks and historic lighthouses to its turn-of-the-century storefronts and bohemian enclaves. Expect wine tastings, barking sea lions and unique art galleries. The seafood is also excellent.

Stay: Elizabeth Oceanfront Suites (Superior)

Meals: B

Day 5

Today, a short-but-scenic coastal drive will bring you past national-forest-backed beaches to historic Florence. Be sure to stop at Cape Perpetua's cragged views and take a short hike to Heceta Head Lighthouse. The Sea Lion Caves are a special favourite. In Florence, you'll stay right on the oceanfront, where views are invited in by elegant rooms and a cocktail bar. Along with the town's quaint waterfront old town, the optional buggy rides in Oregon Dunes National Recreation Area are a genuine trip highlight.

Stay: Driftwood Shores Resort (Superior)

Meals: B

Days 6-7
Grants Pass

Drive a lovely stretch of coastline that includes no fewer than six state parks, two National Wildlife Refuges, and the wildlife area of Cape Arago. Here, you can watch seals and migrating whales. Perhaps stop for lunch at Bandon, the unofficial cranberry capital of the Pacific Northwest, before you arrive in Grants Pass. Ringed by forested mountains, it's the perfect destination for some adventure, from hikes and fishing to white-water rafting and jet-boat cruises. There's also a myriad of wineries to sample before retiring to your historic guesthouse – a former fishing lodge beloved by Walt Disney. The homely cabins are a delight.

Stay: Weasku Inn, Grants Pass (Superior)

Meals: B

Day 8
Crater Lake/Sunriver

Drive along scenic byways to Crater Lake National Park, one of America's most dramatically beautiful places. It's surrounded by sheer cliffs and is the seventh-deepest lake in the world. Be sure to take the the 33-mile drive around the rim for spectacular views before continuing north along the Cascade Lakes National Scenic Byway through Deschutes National Forest. You'll arrive at Central Oregon's high desert and the Sunriver Resort, its rustic chic set to dramatic views of the Cascade Mountains.

Stay: Sunriver Resort (Superior)

Day 9

Although situated on the volcanic Cascade peaks, the town of Bend is surprisingly cosmopolitain, with an impressive range of restaurants and breweries, a vibrant nightlife, and a growing arts scene. It's also world-famous for its outdoor pursuits and pristine beauty, characterised by majestic snow-capped peaks. Indeed, your drive between Sunriver and Bend is blessed by beautiful geological wonders. Don't miss the Newberry Volcano, an 18-mile caldera containing East and Pauline Lakes; The Lava Lands Visitor Centre; and the Deschutes River Trail. It winds through Bend, passing some beautiful cascading waterfalls. 

Stay: Sunriver Resort (Superior)

Day 10

Depart Sunriver via Sisters, and 1880s-themed town, before driving along the McKenzie Pass-Santiam Pass Scenic Byway to take in spectacular views of the volcanic peak and basin. Continuing on the West Cascades Scenic Byway, you'll be treated to some excellent views of thundering waterfalls, lush ancient forests, rushing whitewater and cool, placid lakes. You'll also have the fantastic backdrop of Jefferson and the Three Sisters mountains. Then, heading out along the Historic Columbia River Highway, you'll enjoy panoramic views of the gorge below and the impressive Multnomah Falls, which drop 620 feet. Finally, take the Mt. Hood Scenic Byway to see some of the state's most beautiful scenery, including temperate rainforests, lush valleys and rich pioneer history. In the evening, why not visit one of Portland's microbreweries or wine bars.

Stay: The Benson, Portland (Superior)

Days 11-12
Depart for UK

Drop your hire car off at the airport and board your overnight flight home.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Superior Deluxe

12-day tailor-made self-drive
from £2,340 pp incl. flights


Low Season

from £2,340 pp. incl. flights

High Season

from £3,525 pp. incl. flights


  • Complimentary UK airport lounge access
  • Return flights between London and Portland
  • 10 days Compact hire car and road book
  • 10 nights accommodation in typically 3+* (Standard) and 4* (Superior) hotels on room only basis

High season: June-September

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0636 to discuss how we can tailor your holiday.

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Every step of the way

Every step of the way

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