15-Day Classic Oregon

15-Day Classic Oregon

All-Inclusive | Private Multi-Day Itinerary

15 Day | 14 Night

Whether it’s your first trip to Oregon or your fifteenth, this classic tour of Oregon includes some of the state’s best waysides, natural attractions, historic towns, and foodie hot spots. Let us introduce you to this amazing northwest destination!

EverGreen Escapes van heading to Mt. Hood, Oregon



  • Explore Portland and its eclectic neighborhoods
  • Hike to stunning waterfalls in the Columbia Gorge
  • Make memories at Crater Lake National Park
  • Experience Oregon’s active lifestyle in Bend
  • Soak your toes in the sand at the Oregon Coast


Day 1 | Portland

Arrive in Portland, the Rose City, and meet your guides as you are escorted to your luxurious hotel in downtown. This evening we’ll get to know the sights, sounds, and flavors of the city. From its eclectic neighborhoods to its hip downtown and Pearl district, Portland features endless opportunities for foodies and urban explorers. Finish the night with a welcome dinner, where we’ll review the exciting upcoming itinerary as we explore Classic Oregon!

  • Replenish | Dinner at local farm-to-fork restaurant
  • Sleep | The Nines Hotel

Day 2 | Mt. St. Helens National Monument 

Today we head up and into the Cascade Mountains to visit Mt. St. Helens National Monument, one of our region’s most iconic, well-known, and powerful attractions. Your naturalist will share the drama of the geological events surrounding the 1980 eruption through a variety of stories, facts and walks. Then we’ll turn our headlamps on as we spelunk deep into a lava tube at the Ape Caves.


Gorgeous view of Vista House from Chanticlear PointDay 3 | Columbia Gorge & Mt. Hood

Explore two of the greatest attractions of the Pacific Northwest – the Columbia Gorge and Mt. Hood! Learn the ins and outs of the gorge while spotting for wildlife and hearing tales of historic grandeur, before visiting the historic Timberline lodge at 6,000 feet on Mt. Hood. We’ll visit Multnomah Falls, the tallest waterfall in Oregon and hike to two or three other secluded falls in this lush region.

Day 4 | Salmon River & Hood River

Wake up on the wild side this morning with a half-day on the Salmon River tackling class III and IV rapids.  Then calm your nerves with an afternoon of wine tasting around Hood River.

  • Replenish | Breakfast, lunch at a local cafe
  • Sleep | Skamania Lodge

Day 5 | Eastern Columbia Gorge

The journey along the Columbia River continues as we head east to high desert country. Watch for birds and wildlife roaming the basalt cliffs before heading to the Columbia Gorge Discovery Center for some fascinating history and culture, including the treacherous journey of Lewis and Clark in the early 1800s.

  • Replenish | Breakfast, lunch at a local cafe
  • Sleep | Skamania Lodge

Smith RockDay 6 | Central Oregon

Say goodbye to the lush green landscapes of the Gorge as we travel south and over the Cascades to central Oregon. Stretch your legs with a short nature hike at Smith Rock State Park while watching rock climbers scramble up the geological wonder.  Then enjoy an afternoon exploring downtown Bend.

Day 7 | Mt. Bachelor & Deschutes River

This morning we will head to Mt. Bachelor, a world-class ski resort in winter, to ride the alpine chair for an unbelievable vantage of the surrounding mountains. As we return down the mountain, enjoy scenic waysides and nature walks along the Cascade Lakes byway. After lunch get ready to get your feet wet on an afternoon float on the Deschutes River or guided stand-up paddle boarding excursion.

Day 8 | Bend

Today starts with a morning free to enjoy the resort or ranch. Play a round of golf on the award-winning greens, pamper yourself with a visit to the spa, or take a guided horseback romp around the grounds.  After lunch on your own, we’ll visit the High Desert Museum to learn about the native cultures and wildlife that live in this beautiful landscape. Tonight we spend out on the town with a brewery tour around Bend and then dinner together at Deschutes Brewery.

Day 9 | Crater Lake

As the sun rises over the rolling desert valley, we load up and make our way to the rim of Crater Lake, Oregon’s amazing National Park. Explore the historic lodge, snap ample photos of the azure blue lake and learn about the unique geological history that formed this iconic natural wonder.

  • Replenish | Breakfast, lunch at the rim of Crater Lake
  • Sleep | Weasku Inn

Day 10 | Rogue River & Redwoods

Get your adrenaline going early this morning with a fast and fabulous jet boat ride down the wild Rogue River from Grants Pass. After lunch we’ll depart for the Oregon Coast, where we’ll spend the next few days. En route, we’ll explore the sky-scraping forests at Jedediah Smith Redwood State Park and cozy beaches along the southern shoreline.

Day 11 | Gold Beach

Enjoy a leisurely day with activities at the beautiful Tu Tu Tun Lodge and explore the community and sandy shoreline of Gold Beach.

Day 12 | Florence & Newport

Recharged, we’ll hit the road again and make our way along the Pacific Coast Highway to Newport. Take an exciting dune buggy ride on the central coast’s expansive Oregon Dunes National Recreational Area and wander old town Florence before watching the sunset from Nye Beach.

Day 13 | Cannon Beach

Today we’ll continue our journey north along the Oregon Coast. Visit small secluded beaches on the scenic drive along the Three Capes Loop and spot for spouts with a morning whale watching excursion from the smallest harbor in the world.

  • Replenish | Breakfast, lunch at a local cafe
  • Sleep | Ocean Lodge

Day 14 | Willamette Valley

Boasting more than 300 wineries and tasting rooms, Willamette wine country delivers on elegance but leaves pretense at the door. Tour the vineyards and taste at four award-winning wineries today, while learning about the art of viticulture from an expert guide and sometimes the winemakers themselves.

Day 15 | Departure

Say goodbye to your guides as they drive you back in the morning to Portland for your flight or train ride home.

  • Replenish | Breakfast


Please call for a tailor made version of this incredible adventure
Toll Free | 866-203-7603


The “Rose City” is adored by all who visit, Portland is unique, vibrant, sustainable and beautiful. Iconic views abound of the surrounding volcanic peaks, waterways and dense forest. Explore the quirky neighborhoods, urban parks and learn of the local and natural history, including some of the elements that have caused Portland to be referred to as the most environmentally friendly or “green” city in the United States.

Columbia Gorge

The Columbia Gorge is among the rarest and most fascinating destinations on the planet.  On the Historic Columbia River Hwy one leaves the present behind and travels back to a time when driving was about the journey, and not the destination.  This magical place is home to, abundant wildlife, picturesque towns, breathtaking vistas and majestic waterfalls, even the second tallest perennial waterfall in the US, Multnomah Falls. See the landscape transform before your eyes as you travel from lush wet forests to high desert plains. Be on the lookout for Bald Eagles and Osprey, while admiring the towering basalt cliffs and other fascinating rock formations. On a clear day, white-cloaked volcanic peaks loom over us like sentinels guarding the majestic landscape.  Wonder into a few nearby wineries let the winemakers tell the story of the land, both natural and cultural history, so that with each sip of wine you can begin to understand and experience a little more how the forces that shaped this incredible landscape have also shaped the wine in your glass, creating a terroir that can only be found in this secluded paradise.

Central Oregon & Bend

Situated on the scenic Deschutes River in the geographic center of the state Bend is the most populated city in Central Oregon. To the east is high desert vegetation and to the west, Bend is surrounded by U.S. Forest Service land. The city is noted for its picturesque setting, mild climate, year-round recreation opportunities and growing economy. At an elevation of 3,625 feet, Bend enjoys the predominately dry climate of the Great Basin. Sunny days, cool nights and low humidity characterize the weather. Over the last century Bend has grown from a simple lumber settlement, to the thriving and vibrant urban center it is today with a rich cultural life.

Crater Lake National Park

Crater Lake has inspired humankind for thousands of years. No place else on earth combines a deep, pure lake, so blue in color; sheer surrounding cliffs, almost two thousand feet high; two picturesque islands and a violent volcanic past. It is a place of immeasurable beauty, and an outstanding outdoor classroom.

Oregon Coast

Considered to be one of the best coastal drives in the world, the Oregon coast twists and turns past picturesque lighthouses, charming beach communities, sea lion caves, and coastal monoliths like “Haystack Rock,” in Cannon Beach.  Forage for mushrooms, catch a crab, whale watch, hike or go tide-pooling; soak up nature in all its splendor along the celebrated Oregon Coast. Whatever you do, take a moment to feel the salt breeze on your face, hear the breakers crashing on the beaches and rocky shorelines and enjoy the expansive views.  And don’t forget to take your shoes off to get your toes in the sand!

Willamette Valley

In the past decade Oregon has become a world-class wine state, with 15 approved wine growing regions (AVAs) and more than 300 wineries producing 72 varieties. Our Oregon wine trail experience will introduce to you to some of the Willamette Valleys most acclaimed winemakers in an intimate and relaxed setting. Your private expert guide will be sure the spotlight is on more than just the quality of the wine and enlighten you with the rich ecology of the region, while at each stop will dig a little deeper to explore the local wine making history, the fine art of viticulture and Oregon’s commitment to sustainable farming practices.



Please call for a tailor made version of this incredible adventure
Toll Free | 866-203-7603


  • Pick-up and drop-off each day
  • Travel in adventure-outfitted Mercedes Vans and luxury SUVs
  • Highly qualified Escape Artist naturalist guide
  • Accommodations as described
  • Morning tea, coffee & scones
  • Afternoon refreshments & snacks
  • Breakfast, lunch & dinners as described
  • Local and/or organic fresh fruit
  • Local wine & craft brew
  • All gear related to activities
  • All entry, tasting and/or park fees
  • Comprehensive naturalist commentary and interpretation


Please call for a tailor made version of this incredible adventure
Toll Free | 866-203-7603

How to Pack and Prepare | FAQs | Terms & Conditions

Evergreen Escapes is Cascadia’s premier sustainable adventure travel company based in Seattle and Portland. Providing private and small group naturalist-led adventures in bio-fueled Mercedes vans. Specializing in crafting upscale and authentic nature, epicurean and education based experiences for the responsible, curious and discerning traveler.

We know our destinations, but we don’t know you yet! Even if you’ve been inspired by one of our multi-day tours, we’ll need to know your hotel preferences, activity level, travel style, etc. to craft you the perfect Northwest travel experience and address logistical concerns such as the cost!

The more you share, the better we can source our knowledge, enthusiasm and personal connections to design an Escape Plan personalized to your interests and passions. An expert Escape Artist will contact you shortly to answer any questions you may have and start planning your trip!


Thank you for traveling with Evergreen Escapes!