21-Day Classic Cascadia

21-Day Classic Cascadia

All-Inclusive | Private Multi-Day Itinerary

21 Day | 20 Night

See it all in one trip to Cascadia! From the rain forests of the Olympic Mountains to the golden beaches of the southern Oregon coast and everything in between, this 21-day tour features National Parks, wine country, stunning landscapes, active adventures, and food finds that define the region.  For those interested in gaining a thorough understanding of the Pacific Northwest region, this is the trip you’ve been looking for!

MSR Rainier34


  • Discover the serenity of the San Juan Islands and Olympic National Park
  • Make memories in the Cascade Mountains with visits to Mt. St. Helens, Mt. Hood, Mt. Bachelor and Crater Lake National Park
  • Taste the Oregon difference in Portland with a craft-brew tour and wine tasting in the Willamette Valley
  • Soak your toes into the sand on the Oregon Coast
  • Rediscover your adventurous side in central and southern Oregon


Space Needle Garden of GlassDay 1 | Seattle

Arrive in Seattle, where you are escorted to your luxurious hotel in downtown. This evening join your Escape Artist guide for an exploration of this eclectic city’s unique neighborhoods. See Pike Place Market, check out Lake Union, and learn the history of this city on the water. Tonight, we’ll dine together at a welcome reception and go over our exciting upcoming itinerary!

Day 2 | San Juan Islands

Leave the hustle and bustle for the laid-back island life. Wander Friday Harbor’s downtown and enjoy the town’s culinary treats. You may choose to explore a winery, a lavender farm, sculpture park, or take a kayak out for a spin at Roche Harbor.

  • Replenish | Breakfast, Cascadian Safari Lunch
  • Sleep | Island Inn at 123 West

Day 3 | San Juan Islands

After more exploring, hop aboard a whale-watching trip to seek out the resident orca whale pods that call the area home. These still-mysterious animals have inspired natives of the regions for thousands of years – join the club.

  • Replenish | Breakfast, Cascadian Safari Lunch
  • Sleep | Island Inn at 123 West

Kayaking from Willows InnDay 4 | San Juan Islands

Island hop today, exploring Lopez or Orcas Island by ferry. These less-inhabited islands offer beautiful vistas and great cycling or walking opportunities. Enjoy your last night on San Juan Island watching the sun set at Lime Kiln State Park, where orcas and porpoises often swim right by.

  • Replenish | Breakfast, Lunch at local cafe
  • Sleep | Island Inn at 123 West

Day 5 | Olympic National Park

Cross back to the mainland on the Washington State Ferry, and explore the artist’s colony of Port Townsend, with a possible visit to a local cidery. Discover the ‘banana belt’ of the Sequim area, in the rain shadow of the Olympic Mountains, and then head up to Olympic National Park’s iconic Hurricane Ridge, before settling in at Lake Crescent Lodge for the night.

Day 6 | Hoh Rainforest

Hike near Lake Crescent this morning before making your way into the Hoh Rainforest, the only temperate rainforest in the lower 48 states boasting giant old growth trees dripping with moss and plenty of wildlife. You’ll travel along the rugged Olympic Coast today to tonight’s lodges, before making S’mores on the beach!.

Day 7 | Puget Sound

Take out a kayak this morning, and watch the boats go by on scenic Hood Canal. Enjoy a leisurely day of local exploration, and activities around the resort.

EcoParkResort_MtStHelens_WADay 8 | Mt. St. Helens

Today we will start our trip south toward Oregon with a stop at Mt. St. Helens National Volcanic 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.

  • Replenish | Breakfast, Cascadian Safari Lunch
  • Sleep | Skamania Lodge

Day 9 | Columbia River Gorge

Explore two of the greatest attractions of the Pacific Northwest – the Columbia Gorge and Oregon wines! Learn the ins and outs of the Gorge while spotting for waterfalls and wildlife and hearing tales of historic grandeur, before visiting boutique wineries for sipping and learning about the art of viticulture.

Day 10 | Portland

This morning we drive into Portland to get to know the sights, sounds and flavors of this city with many names – Stumptown, Beervana and Bridgetown to name a few. From its eclectic neighborhoods to its hip downtown and Pearl district, Portland features endless opportunities for foodies and urban explorers. We’ll sample some of Portland’s best beers, urban wines and sweet treats as we also take in Portland’s iconic landmarks, including the International Rose Test Garden, Mt. Tabor Park and Powell’s Bookstore.

  • Replenish | Breakfast, Cascadian Safari Lunch
  • Sleep | The Nines

Day 11 | Willamette Valley

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

  • Replenish | Breakfast, Lunch at local restaurant
  • Sleep | The Nines

Day 12 | Astoria & Cannon Beach

This morning, our destination is Astoria where we’ll start our three-day adventure following the rugged rocky cliffs and soft sandy beaches of the Oregon Coast. Peruse local shops, landmarks and historic monuments before taking interpretive walks along the beach and through a coastal rain forest, all while spotting for abundant marine life and sea birds.

  • Replenish | Breakfast, Lunch at local brewery
  • Sleep | Ocean Lodge

Day 13 | Central Oregon Coast

Continuing south, the morning includes visits to Oswald West State Park to learn about the coastal rainforests and watch surfers at Smugglers Cove, a drive along the Three Capes Scenic Loop, then lunch and beach time in Pacific City. Thensearch for spouts from Pacific Gray Whales and learn about their migration from Alaska to Baja before docking in Depoe Bay, the world’s smallest harbor. Safely back on dry land, we’ll depart for Newport and our overnight accommodations. Once settled in, head down to Nye Beach to dine at one of the city’s delicious fresh-seafood restaurants.

  • Replenish | Breakfast, Lunch at local cafe
  • Sleep | Elizabeth Street Inn

Day 14 | Southern Oregon Coast

Today will start with a quiet morning in Newport and a visit to the Hatfield Marine Science Center to learn about the diverse eco-system that thrives on Oregon’s varied coastline. Departing Newport, we’ll enjoy another scenic drive on our way to Yachats and Florence with stops at the Sea Lion Caves, Heceta Head Lighthouse and other secluded beaches. After a staple seafood lunch in old town Florence, guests can go on a scenic dune buggy ride in the Oregon Dunes National Recreation Area before we continue the southerly drive to Gold Beach.

Day 15 | Redwoods National Forest & Grants Pass

Take it easy this morning and enjoy the riverside serenity of Tu Tu Tun Lodge. The calm day continues as we depart and follow the Oregon coast. Watch waves crash at Boardman State Park and enjoy lunch in Brookings. Then we’ll cross into California for an afternoon exploring the sky-scraping forests at Jedediah Smith Redwood State Park.

  • Replenish | Breakfast, Lunch at local cafe
  • Sleep | Weasku Inn

Day 16 | Rogue River & Applegate Valley

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 historic Jacksonville and enjoy wine tasting around the Applegate AVA and a trolley ride to “ooh and ahh” over the spectacular historic homes. The evening climaxes in Ashland with a performance by the folks at the Shakespeare Festival.

  • Replenish | Breakfast, Cascadian Safari Lunch
  • Sleep | Boutique hotel in Ashland

LonsomeDuck_CraterLakeORDay 17 | Crater Lake National Park

As the sun rises over the rolling desert valley, enjoy a guided walk through Lithia Park and spot for wildlife waking up. Enjoy coffee or tea and morning pastries in the park before 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.

Day 18 | 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 19 | 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 thrive in this beautiful landscape. Tonight we spend out on the town with a brewery tour around Bend and then dinner together at the Deschutes Brewery.

Portland_washingtonparkDay 20 | Mt. Hood & Portland

It’s our last day on the road. As we make our way back to Portland, stretch your legs with a short nature hike at Smith Rock State Park and watch rock climbers scramble up the geological wonder. As we cross over the Cascade Mountains, we’ll stop at historic Timberline Lodge on the slopes of Mt. Hood to take in the mountain’s splendor. Say farewell to Oregon while looking out over the blue and green mountains and dining in style at 6,000 feet.

  • Replenish | Breakfast, Lunch at Timberline Lodge
  • Sleep | The Nines

Day 21 | Departure

Say goodbye to your gregarious guides and start day-dreaming about your next trip to the Pacific Northwest on your flight or train ride home.

  • Replenish | Breakfast



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


 Surrounded by stunning wilderness and waterways, the Emerald City is defined by its natural beauty and eclectic urban charm. Iconic landmarks, historic districts, city woodlands, locks, and Discovery Park, the city’s most spectacular natural preserve are what the locals are most proud of. Spot for wildlife and learn the local and natural history, culture and geology of this diverse region.  Even learn how this city is changing world views on progressive and sustainable initiatives.

Olympic National Park

Discover this gem of a destination with an expert naturalist at your side. Hike the country’s oldest forests down to prehistoric-looking beaches. At the Dungeness National Wildlife Refuge, take an interpretative walk out onto the sand spit. Twice a year, waterfowl and shorebirds descend on these parts. Head up to Hurricane Ridge for a panorama of jagged peaks, alpine meadows, and the sea. Embark on a journey to the wild and rugged coast and the jaw dropping rainforest that makes this park one of only 20 UNESCO World Heritage Sites in North America.

Whidbey Island

Washington’s largest island, Whidbey, provides an impressive diversity of unique natural, historical, and agricultural experiences.  Once the home of several Coast Salish tribes, Whidbey now claims to be Puget Sound’s largest artist community, and supports many well-known painters, writers, and entertainers, among others.  It’s no surprise they choose to live here, considering Whidbey Island’s stunning scenery (Whidbey boasts Washington’s most popular State Park, Deception Pass), wealth of local agriculture (including aquaculture and the world-famous Penn Cove Mussel), and intriguing history (Ebey’s Landing is the nation’s first National Historic Reserve, as established by the National Park Service).  Simply put, Whidbey Island is a fantastic representation of all the best that Western Washington has to offer!

San Juan Island

The San Juan archipelago harbors near-mythical beauty amid its undeveloped islands and seascapes. Its historical relevance is just as intriguing. Spend the day discovering this remote wilderness with a naturalist guide. As the ferry cruises to Friday Harbor, keep an eye out for animals. Embark on a 3-hour orca search by kayak, passing wildlife refuges and rugged coastline. Picnic with local fare and a glass of wine, then explore historic British and American “Pig War” camps. As evening sets, visit an island winery or lavender farm.

North Cascades National Park

Nicknamed the “American Alps” for a reason, this park is one of the most remote and rugged in the U.S.  A hike into its solitude and grandeur is unforgettable. Explore the park’s alpine meadows, cross its rocky ridges, and see the endless sea of jagged peaks veneered by blue glaciers. Spot for black bear, mountain goats and bald eagles, or explore an historic hydroelectric dam.


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.

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.

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.

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.

Columbia River 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.



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

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 Experiencing Cascadia with Evergreen Escapes!