Seven Wonders of Oregon 14-Day Loop

Seven Wonders of Oregon 14-Day Loop

Cannon Beach, Oregon

Private, Multi-Day Tour – 14 Day | 13 Night

Our Seven Wonders of Oregon Loop takes you from sheer desert cliffs to crashing coastline. Explore Oregon’s diverse landscapes through the lens of a private, naturalist guide or go it alone on a self-drive trip packed with the best accommodations and activities that include whale watching, rock climbing, jet boating, caving, and hiking. Along the way you’ll visit all of the Seven Wonders of Oregon: Crater Lake, Painted Hills, Smith Rock, Wallowas, Mount Hood, Columbia River Gorge and the Oregon coast.

From $8,000 for two adults – self drive with accommodations and activities

From $24,600 for two adults – fully-guided by an expert naturalist with accommodations and activities



  • Hike to stunning waterfalls and enjoy vista views in the Columbia Gorge
  • Plunge into the cool blue waters of Crater Lake
  • Discover the eroded sea stacks, hidden beaches, and lonely lighthouses of the Oregon Coast
  • Zoom along the Rogue River on a jet boat tour
  • Wrap your arms around the trunk of a giant redwood tree
  • Experience history in the landscapes of Smith Rock, Painted Hills, and the Wallowa Mountains
  • Cruise into the Pacific on a whale-watching excursion


Views from Washington Park in PortlandDay 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 at a farm-to-fork restaurant where we’ll review the exciting upcoming itinerary as we explore the 7 Wonders of Oregon!

Columbia Gorge ViewDay 2 | Columbia River 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 secluded falls in this lush region.

Columbia River Gorge - 3 Day TourDay 3 | Eastern Columbia Gorge

The journey along the Columbia River continues as we head east to high desert country toward the Wallowas. 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. In the afternoon we will follow the plains as they rise up into rugged alpine summits and our overnight cabin accommodations.

  • Sleep | Cabin near Wallowo Lake or Hotel in Joseph

Day 4 | Wallowa Mountains

This morning, we will take a scenic gondola ride that rises 3,7000 feet from Wallowa Lake Village to the peak of Mt. Howard. From the summit, savor views of the mountains, rolling high desert, and Hells Canyon with a leisurely hike. The afternoon is yours to relax at the lake, go for a hike or visit the quaint downtowns of Joseph and Enterprise to wander their shops and art galleries.

  • Sleep | Cabin near Wallowo Lake or Hotel in Joseph

Painted Hills Seven Wonders of OregonDay 5 | John Day Fossil Beds & Painted Hills

Take a scenic journey through the heart of Eastern Oregon and geological time as we travel to see our Third Wonder of Oregon, the Painted Hills. One of the three units of the John Day Fossil Beds, the Painted Hills get their name from the delicate colored stratification of the low-lying mountains. Millions of year of history are revealed in the colors that can vary from deep red to yellow. After a thorough visit to this dramatic landscape we will continue westward to our ranch accommodations just outside of Bend.

Smith RockDay 6 | Smith Rock & Central Oregon

From one dramatic landscape to another, today we will visit Smith Rock State Park in the morning to get roped up in a half-day rock-climbing class. For first timers and experienced climbers, we can tailor your experience! Not interested in climbing? Hike to the top of Smith Rock for breathtaking views or stay at the resort and pamper yourself at the spa or with a round of golf.

Day 7 | Free Day in Bend

Today, relax with a free day at your leisure in Bend. Choose from activities around the resort or head into town to shop, sample beers along the Bend Ale Trail, or float down the Deschutes River on a raft or Stand up Paddle (SUP) board.

Crater Lake and Wizard IslandDay 8 | Crater Lake National Park

As the sun rises over the rolling desert valley, we embark on a full-day excursion 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. We’ll drive the rim and also enjoy short hikes to scenic viewpoints over the lake.

2011_08_27_015044_AshlandRedwoodsDay 9 | Rogue River & Redwoods

Journey through the southern coastal mountains to the Oregon Coast. Along the way, go deep under the surface on a 1-hour guided tour through Oregon Caves National Monument, look to the sky at the towering redwoods of Jedidiah Smith State Park, and peer over the water at the hidden coves and rock beaches of Boardman State Park. Finish the day with a gourmet, family-style dinner at your accommodations along the Rogue River.

Southern Oregon CoastDay 10 | Gold Beach

Experience the wild Rogue River today on a half-day jet boat ride through this protected wilderness area. Learn about the unique history of this route from your knowledgeable local guide and enjoy the unspoiled beauty and abundant wildlife. To top it off, you may be lucky enough to have a black bear pose for you! For the rest of the afternoon, relax at the lodge, walk along the riverfront, or head into Gold Beach to hike to Otter Point.


Day 11 | 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.

  • Sleep | Elizabeth Street Inn

Cannon Beach, OregonDay 12 | Three Capes Loop & 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.

Day 13 | Astoria & Portland

Our journey finishes today in Astoria where the mouth of the Columbia River meets the Pacific Ocean. Learn about this once thriving fishing village and its rich maritime museum before we turn inland to return to Portland. The rest of the day is yours to explore the city.

Day 14 | Departure

Say goodbye to Oregon as your are transferred to the Portland International Airport for your return flight home.



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 wine makers 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 wine makers 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
  • 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 blends the best natural wonders, boutique wineries, and urban enchantments into small group day tours and private, custom escapes. We’re a small business with a Big Mission: to create positive change in the world by connecting people with places and nature. Our guides aren’t just naturalists, they’re Escape Artists.

We know our destinations, but we don’t know you! 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 Exploring with Evergreen Escapes!