Portland Overnight & Multi-Day Tours

Small-Group Multi-Day Tours from Portland:

Our guided multi-day trips are an excellent way to get more from your time exploring the Northwest. On our small-group trips, you’ll join a few other world travelers, play outside plenty, immerse yourself in world-class landscapes, eat & sleep well, and experience more!

How to join a small group of travelers in the Pacific Northwest on a multi-day tour from Portland:


Choose Your Tour & Date

The multi-day tours below explore ‘can’t miss’ destinations in the Pacific Northwest from Portland, Oregon. Small groups, a great tour guide, and all-inclusive tours. This isn’t a big bus tour – let’s explore!


Traveler Info & Deposit

Click on any of the blue buttons below to see trip specifics and Portland tour booking details. After you’ve decided on your trip – we’ll ask for limited personal info and a deposit to hold your place.


We’ll Take it From There!

You bring appropriate layers and sturdy shoes. We’ll bring everything else: a comfy touring van, an easy-to-love guide, food, plenty of snacks and refreshments, and any gear needed.

3-Day Columbia Gorge National Scenic Area Tour

‘Ultimate Columbia Gorge’ Hiking & Rafting Tour

The Columbia River Gorge offers the perfect mix of nature, adventure, and wine. Hike in Waterfall Alley and the less-visited but more-gorgeous east end, tackle rushing rapids on a whitewater rafting trip, taste wine in Hood River, and more!

Tour Dates 2020

June 28-30
July 27-29
August 17-19
September 21-23

4-Day Crater Lake National Park, Willamette Valley, Bend, & Mt. Hood Tour

‘Beyond Crater Lake’ Walking Tour

This tension-erasing escape visits Oregon’s only National Park – epic Crater Lake, mixes in divine wine from America’s largest grape growing & winemaking region – the Willamette Valley, explores Bend, and winds up Mt. Hood! A more perfect Northwestern adventure isn’t out there…

Tour Dates 2020

July 1-4
July 13-16
August 31 – September 3
September 14-17

5-Day Columbia Gorge, Mt. Hood, Willamette Valley, Oregon Coast, and Portland Tour

‘Oregon Bucket List’ Walking Tour

To really know everything from shoreline to timberline could take a lifetime, but this adventure combines the region’s calling cards into a journey you’ll never forget. From waterfalls to snowfall, and splashing waves to wine splashing in the glass, this is our ‘can’t-miss’ best of Oregon tour!

Tour Dates 2020

June 22-26
July 6-10
July 20-24
August 10-14
August 24-28
September 7-11

Contact our team to learn more about Portland tours.

Ask A QuestionView Seattle Multi-Day Tours

Private Multi-Day Tours from Portland
New Webpages Coming this Summer!

While the scheduled small-group multi-day tours found above are also available as private escapes – the tours below are only available as private explorations. Contact our team to learn more or to schedule your private multi-day adventure today!

2-Day Oregon Coast Private Tour

2-Day Columbia River Private Gorge Tour

2-Day Willamette Valley Wine & Waterfalls Private Tour

3-Day Bend, Oregon PrivateTour

Prefer to browse single-day tours instead?

1-Day Tours from Portland1-Day Tours from Seattle

Multi-Day Tours from our Sister Company – Bicycle Adventures!

Evergreen Escapes shares the Pacific Northwest with our lovely sister company – Bicycle Adventures! Looking for an escape on a date we don’t offer a trip or want a long cycle ride in a beautiful place? Look no further – Bicycle Adventures! The links below will take you to their website.

4-Day Tour: Bend Breakaway

The ultimate cosmopolitan mountain town…snowcapped peaks punctuate the high-desert skyline. Roads are dreamy-smooth. And the weather? Some of the best in Oregon!

learn more

6-Day Tour: Hells Canyon Bike

Open prairie vistas and serene farmland into the breathtaking Eagle Cap Wilderness. Alpine lakes surrounded by the Wallowa Range. Take a tramway to the top of Mount Howard & ride deep into Oregon’s Hells Canyon.

learn more

8-Day Tour: Oregon Coast to Crater Lake

Cross the Coast Range and sail down the knobby headlands of Oregon’s craggy southern seaboard – turn inland to follow the Wild and Scenic Rogue River toward Crater Lake!

learn more