Oregon Coast to Cascades Private Journey

From Seascapes and Wine Country to Glacier-Clad Mountains


With wild Pacific shores, lush vineyards, and the towering peaks of the Cascades, Oregon is a wildly diverse state that beckons with endless adventure. On this delightful Private Journey, you’ll hike the trails, explore by sea kayak, bike in wine country, and taste superb wines as you move from the tide pools of the coast to the acclaimed vineyards of the Willamette Valley, then onward to iconic Mount Hood and the awe-inspiring Columbia Gorge, where the mighty Columbia River cuts through the Cascade Mountains. Daily activities with your private guide are tailored just for you, with fun add-on options that include rafting, paddle boarding, a horseback wine tour, and even a sightseeing flight. Prepare to be dazzled by Oregon’s natural beauty!

Itinerary at a Glance

Days 1-2
Portland / Coastal Hikes and Kayaking

From Portland, head to charming Cannon Beach on Oregon’s hauntingly beautiful coast. Experiencing the coast both by kayak and on foot, you’ll paddle in protected coves, keeping an eye out for wildlife, then follow majestic clifftop trails, explore tide pools, and enter the quiet world of magical temperate rainforests. Enjoy a cooking class/dinner show, with optional add-ons including a private yoga class, a fat-tire bike ride on the beach, a surf lesson, or a scenic drive with craft beer tasting. Your hotel is set right on the beach.

Surfsand Resort
Cannon Beach, USA
Days 1 to 2 (2 nights)
Stephanie Inn (Optional Upgrade)
Cannon Beach, USA
Days 1 to 2 (2 nights)
Day 3
Willamette Valley Wine Country

Heading to renowned Willamette Valley wine country, bike a portion of the Banks-Vernonia Trail, a fully paved “rails-to-trails” path through a wonderfully pastoral setting. Taste wines at three vineyards, complete with a picnic lunch and vineyard hikes. Your accommodation is a luxury inn and spa. Optional add-ons include Willamette River kayaking with lunch, a horseback wine tour, and a fun cooking class/dinner at the Kitchen at Middleground Farms.

Allison Inn and Spa
Willamette Valley, USA
Day 3 (1 night)
Days 4-6
Mount Hood / Columbia Gorge / Hiking, Winery and Brewery Tours

Explore Mount Hood (11,240’), with lunch at elegant Timberline Lodge, a National Historic Landmark built in 1937, and a choice of hikes including the famed Pacific Crest Trail, Trillium Lake, or Tamanawas Falls. Travel through the picturesque Hood River Valley, with its farm stands amid orchards, vineyards, and lavender fields. Spend a day hiking panoramic trails in the Columbia River Gorge National Scenic Area, and tour innovative local breweries. Overnights are at a farm-style bed and breakfast in a pear and apple orchard. Return to Portland on Day 6 by way of a tour of the Columbia River Gorge National Scenic Area. Optional add-ons include kayaking, whitewater rafting, a winery tour by bike, mountain biking, and a sailing tour of the Columbia River.

Sakura Ridge
Hood River, USA
Days 4 to 5 (2 nights)

Optional Add-On's Include:

  • Beach Yoga
  • Cooking Class
  • River Kayaking
  • Horseback Riding
  • Whitewater Rafting
  • Mountain Biking, Road Biking, Fat-Tire Beach Biking
  • Sailing Tour of Columbia River
*Ask our Area Specialist for details about each of these options



Explore the dramatic seaside trails at Ecola State Park, sea kayak along the coast
Bike a “rails to trails” path through pastoral farmlands
Go wine-tasting in the Willamette Valley’s best vineyards
Hike on mighty Mount Hood and in the stunning Columbia River Gorge
Taste the local craft beers, take a cooking class to savor Pacific Northwest’s best cuisine
Enjoy delightful accommodations, from a luxury spa to a cozy farm-style bed and breakfast
Choose optional biking, kayaking, horseback wine tour, and paddle boarding adventures


Length: 6 days
Cost From: $4495  
Arrive: Portland, Oregon
Depart: Portland, Oregon
Lodging: 5 nights boutique hotels and lodges
Meals: All meals included except 2 lunches and 3 dinners as indicated in the Detailed Itinerary (B=Breakfast, L=Lunch, D=Dinner)
Activity: Sea Kayaking, Hiking / Trekking, Bicycle Tours, Culinary
Trip Level:

Hiking, kayaking, and biking, tailored to be as relaxing or strenuous as you wish