Oregon Multisport & Wine Adventure

“A bottle of wine contains more philosophy than all the books in the world.”

Louis Pasteur

From its rough-and-tumble coastline to volcanic mountains, crystal-clear lakes, and high deserts, Oregon offers unparalleled diversity in landscapes and beauty.

What you might not realize is that the state is also a world-class wine region with 17 distinct winegrowing regions and more than 450 wineries producing 72 varieties of grapes (including renowned Pinot Noirs that have won many awards in recent years)!

However, Oregon is still in its infancy as far as wine tourism is considered. Oregon’s wine country is spread over thousands of acres and dominated by small, family-run wineries. Each owner and vintner we meet has a great story and we will hear many of them as we taste the local Pinot Noir, Chardonnay, Pinot Gris, and Riesling wines.

On this five-day active wine adventure, we visit wine regions ranging from the Columbia Gorge to the hip college town of Eugene to the base of Mt. Hood, to the northern Willamette Valley . . . and explore the areas by foot and by bicycle.

All this makes our wine adventure in Oregon unique and special. Join us and be in the vanguard of active wine tourism!

Trip Favorite Moments & Reviews

“I enjoyed the variety of activities and, honestly, I learned a great deal about winemaking – while having a blast doing so! The little touches by our guides all hit the spot too.”

Chris P.

“Classic Zephyr. Got to experience and explore most of Oregon wine while keeping active!”

Edward L.


Book this Tour

Past Traveler Tour Rating

4.8/5 stars

Trip Highlights

  • Explore the vineyards of large and small wineries throughout several Oregon AVAs (American Viticultural Areas)
  • Hike on beautiful Mt. Hood
  • Bike along scenic pathways through Oregon's wine country
  • Enjoy gourmet dinners, private wine tasting and tours at award-winning wineries, and a lovely olive oil tasting like you’ve never experienced
  • Visit fun towns of Hood River, Salem and Eugene

We'll meet you in Portland after lunch and travel east into the Hood River Valley. On the way, we stop for a quick peek at one of Oregon’s biggest attractions: the 620-foot high Multnomah Falls. From there, we begin our exploration of the wines of the Columbia Gorge AVA (American Viticultural Area) with a vineyard walk and tasting at one of the many great local wineries. Afterward, we can choose to explore the cute downtown of Hood River, or take in some more wines at the tasting room of Naked Wines (yes, this place is as fun as it sounds - full of double entendres!) before checking into our river view rooms overlooking the mighty Columbia River.


Enjoy a scenic breakfast on the hotel restaurant’s deck this morning, overlooking the bustling Columbia River. After that, get your hiking duds on! Destination: the historic Timberline Lodge at the base of the impressive snow-capped Mt. Hood. Choose from a casual stroll with a ranger, a hike on the Pacific Crest Trail along the base of the mountain, or a strenuous uphill hike to the Silcox Hut (and then back down). Or, if you want to soak in the mountain atmosphere, simply enjoy a leisurely lunch in the Lodge and then ride the chairlift up and watch the summer skiers having fun in the sun. After lunch, we shuttle south and into the heart of Oregon Wine Country: the large Willamette Valley AVA. We spend our afternoon in the small sub-AVA of Eola-Amity Hills, which is unique because of the breeze that arrives from the Pacific Ocean through the Van Duzer Pass, the lowest point in Oregon’s Coast Range. Late in the afternoon on warm summer days, the Van Duzer winds bring cool marine air to the ripening grapes, giving complexity, balance, and finesse to the wines. We walk a couple of miles through the vines of contiguous vineyards such as Bethel Heights, Cristom, Temperance Hill, and St. Innocent, tasting along the way. Amongst the vines, we’ll share the history of the region and the wines that come from this beautiful region. And if you want to purchase wine at our stops, no problem! Our van will pick up any bottles you buy. As the day winds down, we’ll travel to the town of Salem, and our hotel for the evening.  Tonight, we'll enjoy a delicious dinner at DaVinci’s. They, of course, have an excellent wine list!


Today while the air is still cool and with the early morning sun shining on the colorful vines, we will head north by bicycle on one of the best cycling routes in the country into the heart of the Willamette Valley.  When the Willamette Valley AVA was first authorized in 1984, its geographic description included some 3.3 million acres! Twenty-plus years later, winemakers and wine growers succeeded in creating six sub-regions within the Willamette Valley, to better describe micro climates proven over the years to be distinctly suited for the growing of wine grapes. Natural boundaries and the Willamette River create the 100-mile long, 60-mile wide Willamette Valley, home to more than 200 Oregon wineries and many wine shops. Coolest of Oregon’s wine regions, this elongated, V-shaped valley is bordered to the north by the Columbia River, to the south by the Calapooya Mountains (south of Eugene), to the east by the Cascade Mountain foothills, and to the west by Oregon’s Coast Range. A few hours later, we will end our ride at Champoeg State Park, refreshed, and certainly ready for a delicious lunch in the town of Dundee. We heartily recommend the tasty fare at the Red Hills Market!  After lunch, the folks at Red Ridge Farms will welcome us, and we will spend the afternoon exploring their beautiful estate by foot, sipping their wines and learning about the olive oil they produce, and how to properly taste it! This afternoon’s vineyard walks across the Dundee Hills AVA will take us several miles across swaying terroir. Afterward, we head further south into the Southern Willamette Valley’s vineyard-strewn hills and on the town of Eugene, our cozy hotel, and a casual dinner, perhaps with Oregon’s “other” famous beverage (beer).


After a yummy breakfast in our hotel, we enjoy a brisk two-hour hike up and down the iconic Spencer Butte.  All that hiking will build your appetite and our lunch and tasting at Oregon’s largest winery – King Estate  –  will not disappoint.  You may want to sneak in a catnap in the sun before our guided tour.  We spend the evening at our darling hotel with a wine-pairing dinner in their fine restaurant. Your guides will try to convince you to go out afterward and explore this hip college town with them.


This morning you can choose to have a leisurely morning, perhaps sleeping in, before enjoying breakfast. Otherwise, we will do as the natives love to do by biking as many of the dozens of miles of bike trails and lanes in and around Eugene you desire. We turn you loose armed with maps and a variety of mileage choices for a fun bike ride along Eugene’s river paths. We’ll get you back in time to shower and pack up before getting you to the airport or Amtrak station for an afternoon flight or train back to Portland.

Book this Tour

Trip Accommodations


It’s not often you get a view like this! Panoramic views of the Columbia River from your porch or patio, plus a private beach, and a new pool, hot tub, and fitness facility at river's edge will all make your stay ultra memorable.


Located in the heart of downtown Salem, the Grand is consistently rated the top hotel in Salem. You'll see why when you make yourself at home in your spacious and well-appointed room.


This intimate boutique B & B has a warm and cozy atmosphere and has only 14 rooms, each of them unique and each named for classical composers. Its location offers easy walking access to the vibrant University area of one of our absolutely favorite towns.

Book this Tour
Arrival & Departure

We begin in Portland and end in Eugene, two of the hippest and most fun towns in Oregon. Your Zephyr guides will meet you in either downtown Portland or at the Portland airport (code PDX) on the first afternoon of the trip. On the last day, we will drop you off at the Eugene airport (code EUG) or the Eugene Amtrack station, where you can catch a flight home or a train back to Portland. You should either purchase an “open-jaw” ticket that flies into Portland and out of Eugene or simply purchase a round-trip ticket to either city, allowing time for a train ride from Eugene to Portland either prior to the start of the trip (if flying in and out of Eugene) or after the trip (if flying in and out of Portland). We will send you further details upon booking.

What's Included?
  • At least two Zephyr guides accompany each trip and a third is added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room. Due to limited space at the wilderness lodges, there are only a few single supplements available for this trip.
  • All of your dinners and breakfasts are included, as well as lunch on Day 4. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • All trail fees and permits are included.
  • Bicycle rentals and wine tastings costs are included.
  • NOT INCLUDED Beverages, desserts, chairlift ride (optional) at Timberline Lodge, gratuities to your guides, personal expenses, and travel to and from the destination.

The average high temperature in August in the wine areas of Oregon is 80 degrees Fahrenheit, while the average lows are in the 50s. Plus, while western Oregon does get its share of rain, July and August are the driest months. So, expect hot, sunny days with little chance of rain.

Extending Your Stay

We don’t visit Portland at all during our tour and would highly recommend staying an extra day in this city. If you would like to extend your vacation even longer, two fantastic trips within Oregon are the coast and the Bend area. The Oregon Coast is renowned for its waves, beaches, and cute small towns. Bend, located in central Oregon, is a great outdoors town and a center for mountain biking, hiking, river rafting, and pretty much anything else you want to do.

Do I Need To Be A Wine Expert To Enjoy This Tour?

You definitely don’t need to be a wine expert to enjoy this tour. In fact, you don’t even need any knowledge of wines at all. All you need is an open mind, an ability to discern what you like and don’t like, and an adventurous spirit.

Ability Level

The Oregon Multisport Wine Adventure is rated for All Abilities. The hiking is gentle, the biking is gradually downhill, and no experience is required on any of our activities. We will provide more difficult challenges for those who wish them but, otherwise, this tour is designed to be a fun, active, but not challenging trip.

Changes to Your Itinerary

While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.


Book this Tour

I'm Interested

I really want to join this trip but can't book quite yet. Put me on the Interested List.

More Information

I'm interested in this tour and want more information. Get in touch with us.

Plan a Private Tour

Looking to book this itinerary as a private tour? Complete our private tour inquiry form to get started.

Get Travel Inspiration Delivered Directly to Your Inbox

Sign up for our newsletter to receive regular updates on our upcoming adventures.