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Oregon wine country

Oregon Fly-Drive

11-day tailor-made self-drive from £1,330 pp incl. flights

Special offer: Save up to £540pp


Short description

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


  • Explore Portland's artisan food scene and artistic innovations
  • Take in the dramatic beauty of Crater Lake National Park
  • Visit Newport's famed aquarium, a centre for marine conservation
  • Ride a buggy through the Oregon Dunes National Recreation Area
  • End with a stay in Sunriver, a region of outstanding natural beauty

In Brief

  • 1 Night 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 USA fly-drive starts in the beautiful city of Portland, Oregon, before taking in Newport, Grants Pass, Sunriver and the beautiful Crater Lake National Park. Beginning in trendy Portland, you'll explore the city's thriving arts and dining scenes before driving out to Newport, the heart of Oregon Wine Country. As you head south along the spectacular Scenic Byway, call into historic lighthouses and sleepy fishing villages, all framed by spectacular Pacific Ocean views. Visit Newport's Oregon Coast Aquarium to watch playful sea lions, seals, and otters. Then, driving to Florence, you'll pass through verdant spruce forests, stopping to take an optional buggy adventure in the Oregon Dunes National Recreation Area before nights at Grants Pass, Sunriver and Bend bring your tour to a fittingly scenic conclusion.

Day by day itinerary

Day 1
London - Portland

Catch your flight from London to Portland. On arrival, start your self-drive in Portland, a hip urban outpost known for its cuisine, vibrant arts scene, and funky shopping districts. The city had many intriguing neighbourhoods, each with its own unique flavour and heritage. For arts, nightlife and fashion, head to the Pearl District, whilst Nob Hill has plenty of boutique shops. Visit Old Town Chinatown for entertainment - it's home to the famous Portland Saturday Market, Voodoo Doughnut and Lan Su Chinese Garden. Don't miss the historic Mississippi Avenue, that combines originality, variety, style and energy. 

Stay: Benson Hotel

Day 2

Today, you will travel through the heart of Oregon Wine Country, with over 100 wineries, on your way to the magnificent Oregon Coast. As you head south along the spectacular Scenic Byway, you will pass historic lighthouses, sleepy fishing villages and amazing vistas. See the gorgeous seven miles of beach in Lincoln City, and stop at the charming Depoe Bay, which has spectacular views of the Pacific Ocean. Newport’s Historic Bay Front is home to one of Oregon’s largest commercial fishing fleets, and you'll see shops, art galleries, restaurants, fish processing plants and turn-of-the-century storefronts. 

Stay: Elizabeth Oceanfront Suites

Meals: B

Day 3

Newport is located between coastal mountains, the Pacific Ocean and Yaquina Bay, in an area of great natural beauty. Top attractions include the Yaquina Head Lighthouse, and the Oregon Coast Aquarium. 

Stay: Elizabeth Oceanfront Suites

Meals: B

Day 4

Today, your drive will be short. Stop at Cape Perpetua, an exquisite natural landmark, before taking a short hike to the Heceta Head Lighthouse. Don't miss the Sea Lion Caves, before you reach the delightful and historic Florence. In the afternoon, take an optional dune buggy ride in the Oregon Dunes National Recreation Area on 47 miles of sand. 

Stay: Driftwood Shores Resort

Meals: B

Day 5
Grants Pass

Drive the Charleston to Bandon Tour Route today, which is a lovely stretch of coastline that includes six state parks, two National Wildlife Refuges, and the wildlife area of Cape Arago where you can watch seals and migrating whales. Stop for lunch at Bandon, the unofficial cranberry capital of the Pacific Northwest. Enjoy some magnificent coastal scenery before you head inland to Grants Pass.

Stay: Weasku Inn, Grants Pass (Superior)

Meals: B

Day 6
Grants Pass

Grants pass is a classic river town that's ringed by forested mountains. Enjoy its history, friendly small-town atmosphere, myriad of wineries and scenic byways or just relax in the tranquil setting of Weasku Inn.

Stay: Weasku Inn, Grants Pass (Superior)

Meals: B

Day 7
Crater Lake/Sunriver

Drive along scenic byways to Crater Lake National Park, one of America's most dramatically beautiful places. Crater Lake is surrounded by sheer cliffs, and is the 7th deepest lake in the world. Be sure to take the the 33-mile drive around the rim for spectacular views. Continue north and take the Cascade Lakes National Scenic Byway through Deschutes National Forest on your way to Central Oregon's high desert and the Sunriver Resort. 

Stay: Sunriver Resort

Day 8

Situated on the volcanic Cascade peaks, the town of Bend is cosmopolitain, and has an impressive range of restaurants and breweries, a vibrant nightlife, and a growing arts scene. The town is also world famous for its outdoor pursuits and pristine beauty, and majestic snow-capped peaks. Between Sunriver and Bend the land is covered in beautiful geological wonders. Don't miss the Newberry Voclano, an 18-mile caldera containing East and Pauline Lakes, The Lava Lands Visitor Centre, and the Deschutes River Trail that winds through Bend passing some beautiful cascading waterfalls. 

Stay: Sunriver Resort

Day 9

Depart Sunriver via Sisters, and 1880s themed town, before driving along the McKenzie Pass-Santiam Pass Scenic Byway along which you'll see lava fields next to calm, clear lakes. Stop at the Mt. Washington Scenic Overlook, which offers spectacular views of the volcanic peak and basin. Continue on the West Cascades Scenic Byway, that has some excellent views of thundering waterfalls, lush ancient forests, rushing whitewater and cool, placid lakes. You'll also have excellent views of Jefferson, Washington, Three Fingered Jack, 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 drops 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 a microbrewery, wine bar or art enclave. 

Stay: The Benson, Portland (Superior)

Day 10
Depart Portland

Enjoy some last minute tax-free shopping, before boarding your plane and departing Portland. Board your overnight flight to London.

Day 11
Arrive UK

Arrive in London and continue your journey home.



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

Accommodation rating: Superior Deluxe

11-day tailor-made self-drive from £1,330 incl. flights


Special Offer

Save up to £540 pp.

Book by: 15 June 2019

Low Season

from £1,330 pp. incl. flights

High Season

from £1,775 pp. incl. flights


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

High season: Jul-Aug

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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