Oregon's Mountains, Coasts, and Valleys

Discover the stunning natural scenery, culinary delights, and diverse wonders of beautiful Oregon. Explore the the Hood River Valley by bicycle. Practice yoga with the rocky coastline of Cape Kiwanda as your backdrop. Hike through ancient forests to some of the 90+ waterfalls found in the Columbia Gorge National Scenic Area, set against nearby peaks of the Pacific Northwest's Cascade Mountain Range. Sip wine in the Willamette Valley and try your hand at cooking the freshest local ingredients to fully appreciate the bounty of this region. Welcome to Oregon where adventure awaits!

Daily Itinerary

Day 1: Arrive Portland

Arrive Portland
Daily Summary
  • Transportation: Airport Transfers
  • Other: Portland Welcome Dinner
  • Accommodation: Dossier Hotel
  • Meals: D

Upon arrival to Portland, you will be picked up at the airport and transferred to your hotel in the city.

Portland Welcome Dinner

Portland's thriving restaurant scene is full of character, prestige, and plenty of farm fresh local ingredients. The creative and entrepreneurial spirit of the city means there's a plethora of options for a welcome dinner. From an exclusive tasting menu hosted by a James Beard award wining chef to a progressive dinner tour, the sky's the limit for a memorable welcome to Portland. (This service is on a private basis.)


The Williamette Valley was inhabited by indigenous Chinook people prior to pioneers founding a settlement near the ending point of the Oregon Trail in the 1830s. Over the course of its near 200 year history, the city evolved from rough and tumble port town to the progressive counterculture hotspot it is today. Portland is home to approximately 2.4 million people and is the largest city in the state of Oregon. While "Portlandia" is jokingly said to be "stuck in the 90s" with flannel shirts and a laid back feel, it is well respected as a leading green city, has a thriving coffee culture, numerous local breweries, and a flourishing arts scene. The city has many excellent spots to visit such as Washington Park home to the International Rose Test Garden, the Portland Japanese Garden, and hiking trails like Wildwood Trail, Maple Trail Loop, and more.

Day 2: Portland - Pacific City

Portland - Pacific City
Daily Summary
  • Tour: Oregon Coast Tour
  • Accommodation: Headlands Coastal Lodge & Spa
  • Meals: L, D

Oregon Coast Tour

Located an hour and half from Portland, lies Oregon Coast's rugged and spectacular coastline traced by jutting headlands and dotted with awe inspiring vistas, lush old-growth forests, and Maritime community charm.

On this full day tour, your private guide will show you some of Oregon's most treasured state parks by foot and wide open shorelines by fat bike. You'll enjoy sea-views at a local brewery and end your day with a bonfire and s'mores on the beach. (This service is on a private basis.)

Pacific City

Perhaps best known for the stunning coastline of Cape Kiwanda, Pacific City is a peaceful beach side town perfectly positioned for hiking, kayaking, walks along the shore, and is a mecca for surfing. Explore Kiwanda and Sitka Sedge State Natural Areas, Whalen Island, or nearby Bob Straub State Park nestled between the Nestucca River and Pacific Ocean.

Day 3: Pacific City - Willamette Valley

Pacific City - Willamette Valley
Daily Summary
  • Tour: Cape Kiwanda Hike
  • Accommodation: The Allison Inn & Spa
  • Meals: D

Cape Kiwanda Hike

This morning, the ocean is your backdrop for an early wellness activity to start your day. Enjoy a guided beachfront yoga session or ascend the sand dune slope of Cape Kiwanda for a meditative hike and dramatic sea cliff views. (This service is on a group basis.)

Spend an evening at a family-run winery nestled in the Chehalem mountainside. Hazelfern focuses on making high-quality small lot wines and is a boutique producer of Chardonnay and Pinot Noir. After sampling through their catalog we'll enjoy a cellar dinner in the beautifully renovated tasting room barn. (This service is on a group basis.)

Willamette Valley

The heart of Oregon Wine Country, the Willamette Valley stretches approximately 150 miles north to south along the Willamette River. The Cascade Range and Oregon Coast Range provide natural east and west borders, while the Calapooya Mountains are found just to the south. The region's rolling hills and cool moist climate are an ideal environment for vineyards producing some of the finest Pinot Noir in the world.

Day 4: Willamette Valley

Willamette Valley
Daily Summary
  • Tour: Willamette Valley Wine Tour
  • Accommodation: The Allison Inn & Spa
  • Meals: L, D

Willamette Valley Wine Tour

On this full-day private guided tour you'll spend the morning at the region's largest and most renowned winery, Willamette Valley Vineyards, where you'll immerse yourself in wine country with a traditional grape stomp followed by a wine-pairing lunch from the terrace of the estate's panoramic tasting room.

Later this afternoon, you'll venture to Red Ridge Farms and Durant Vineyards, a unique property that's home to the only Olioteca (specialty producer of high quality olive oil) in the Pacific Northwest. Your guide will provide a walking tour of the vineyards and olive grove, followed by a chance to learn about their state-of-the-art Italian olive mill. To top it off you'll enjoy a wine tasting and incredible sweeping valley views. (This service is on a private basis.)

This evening, roll up your sleeves for an immersive on-farm cooking class where you'll learn to prepare a gourmet meal using local seasonal ingredients. Enjoy a nibble and wine along the way before digging into your culinary creation. (This service is on a group basis.)

Day 5: Willamette Valley - Columbia Gorge

Willamette Valley - Columbia Gorge
Daily Summary
  • Tour: Mt. Hood Excursion
  • Tour: Dinner and Wine Tasting at Marchesi
  • Accommodation: Sakura Ridge
  • Meals: L, D

Mt. Hood Excursion

From the Willamette Valley we will wind our way up to Oregon's tallest peak, Mt. Hood, and spend the day exploring the mountain's historic and natural treasures. First stop will be Timberline Lodge, a National Historic Landmark and home to the only year-round skiing in North America. After touring around the Cascadian style lodge, we'll have lunch with stunning mountain range view, followed by a short hike to the Pacific Crest Trail crossing just behind the lodge. From there we'll have the opportunity for several different hikes either along the shoreline of Trillum Lake or up to Tamanawa Falls. Skirting along the east side of Mt. Hood is the picturesque Hood River Valley, home to the "Fruit Loop" a collection of orchards, vineyards, farms, and lavender fields. We'll stop in at one of the many farm stands to pick up some local produce for a late afternoon snack. (This service is on a private basis.)

Dinner and Wine Tasting at Marchesi

Located on the Heights of Hood River, Marchesi Vineyards is a small boutique winery specializing in Italian Grape varietals. Reminiscent of Piedmont, Italy, where the owner and winemaker Franco Marchesi was born and raised, we'll sample varietals such as Barbera, Dolcetto, Pinot Grigio, and Pinot Noir alongside an intimate dinner on the patio overlooking the vines. (This service is on a group basis.)

Columbia River Gorge

Located approximately 100 miles east of Portland between Oregon and Washington states. The Columbia River Gorge is the largest national scenic area in the United States at 292,500 acres. The region is made up of a diverse mix of landscapes including desert, alpine meadows, and lush forests along the the Columbia River through the Cascade Range. Its rich history dates back over 10,000 years when Native Americans first lived in the region and on to European explorers and later Oregon Trail pioneers settling and the development of industry in more recent times. The Gorge has an abundance of hiking trails with stunning views of the various terrains and the greatest concentration of waterfalls in North America including the famous 620ft Multnomah Falls. In addition to trekking, visitors can find excellent skiing, snowboarding, kayaking, biking, rafting, and more at their fingertips.

Day 6: Columbia Gorge

Columbia Gorge
Daily Summary
  • Tour: Hood River Valley Bike Tour
  • Tour: Columbia Gorge National Scenic Area Tour
  • Accommodation: Dossier Hotel

Hood River Valley Bike Tour

Take a serene tasting tour through rural private roads and orchards along the east side of the lower Hood River Fruit Loop known as Pine Grove. This guided tour has an abundance of historical charm and natural beauty – with century old farms, vineyards, historical sites, and breathtaking views of both Mount Hood and Mount Adams along the way. There's a broad range of tasting options including Farm-to-Food-Truck lunch experience, kombucha, cider, beer, and multiple seasonal farm stops along the way! (This service is on a private basis.)

Columbia Gorge National Scenic Area Tour

Enroute back to Portland, we'll explore the Columbia River Gorge National Scenic Area, home North America's most concentrated stretch of waterfalls. Driving along the oldest scenic highway in the US, and stop at sweeping viewpoints, flowing falls, a historic lodge, and more. (This service is on a private basis.)

Day 7: Columbia Gorge - Portland

Columbia Gorge - Portland
Daily Summary
  • Tour: Washington Park Hiking Tour
  • Transportation: Airport Transfers

Washington Park Hiking Tour

Washington Park is Portland's centerpiece of monuments, parklands, gardens, old reservoirs, and even a stretch of natural forest. This loop hike will begin at the monuments, take you through the landscape of the old zoo, then up to the Wildwood Trail to the Portland Japanese Garden and, finally, Portland's world-renowned International Rose Test Garden. Although only four miles, the walk invites many stops and explorations, so you could spend an entire day investigating the various sights. (This service is on a private basis.)

This afternoon, you will be transferred to the airport in good time to board your flight home. We hope you had an amazing experience exploring Oregon with us!


Dossier Hotel

Dossier Hotel

This downtown Portland hotel embodies the city’s cultural ethos, in harmony with its natural surroundings. Each of Dossier’s art-filled rooms and suites features locally-inspired amenities designed to bring the spirit of Portland into the hotel. Wake up refreshed and ready to explore the region’s endless opportunities for adventure, culture, and cuisine.

Headlands Coastal Lodge & Spa

Headlands Coastal Lodge & Spa

An inviting sanctuary on the stunning Oregon coastline. Sink into the pillow-top bedding, a restorative bath or a plush seat by the gas fireplace. Watch the waves from your private balcony. Experience the colors and textures of the Northwest in the comfortably elegant design and furnishings. Enjoy easy access to spa and wellness options, outdoor hot tub, Meridian restaurant and bar, concierge services and more.

The Allison Inn & Spa

The Allison Inn & Spa

An oasis in beautiful Oregon Wine Country, the Allison Inn & Spa is the perfect base for luxurious restoration and exploring the region's 500+ wineries. Enjoy mountain views, spa services, and easy access to local vineyards where a glass of Pinot Noir awaits.

Sakura Ridge

Sakura Ridge

Located on a pear and apple orchard, this farm-style bed & breakfast blends pasture views with a snow-capped backdrop of Mt. Hood. The onsite garden and farm provides an abundance of fresh ingredients which appear on the breakfast table daily. While guest rooms have an intimate cozy lodge feel, complete with private decks and rocking chairs.

Pricing and Details

Starting from $ 8,125 per person

*Pricing is based on two persons traveling together, based on availability, subject to change.

Price Includes

  • Full support before, during & after your trip
  • Meals as mentioned
  • Accommodation as mentioned
  • Tours/activities as mentioned
  • Transport as mentioned

Price Excludes

  • International & domestic flights
  • Travel insurance (highly recommended)
  • Entrance visas when applicable
  • Other services not mentioned
  • Tips and gratuities to guides, drivers
  • Taxes and fees

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