Top Oregon Private Sightseeing Tours

Q: What are the best options for Oregon Private Sightseeing Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Oregon Private Sightseeing Tours are: Guided Jetboat Tour for Six -Private Private Group Tour up to 11 of Columbia River Gorge & Waterfalls from Portland Private Wine Tour with Tastings from Eugene Private Tour of Multnomah Falls and Columbia Gorge Custom Willamette Valley Wine Tours from The Allison Inn and Spa

Q: What are the best kid-friendly options for Oregon Private Sightseeing Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Oregon Private Sightseeing Tours are: E-bike in Oregon’s Columbia River Gorges Full Day Jet Boat Tour in Hells Canyon Eugene area Waterfalls & the McKenzie River in a Tesla Guided Jetboat Tour for Six -Private Tasting the Gorge by Ebike View all kid-friendly Tours →

Q: Which Oregon Private Sightseeing Tours have Instant Confirmation?

Oregon Private Sightseeing Tours with Instant Confirmation include: Private Tour at The Hood-Columbia Loop: Timberline, Orchards, and Waterfalls Private Northern Oregon Coast Day Trip Private Multnomah Falls and Mt. Hood Tour with Gorge Waterfalls Private Northern Oregon Coast Tour Private Mount St. Helen's Volcano Tour View all Tours with Instant Confirmation →

Q: I need a ride! Which Oregon Private Sightseeing Tours have Hotel Pickup?

No problem. These Oregon Private Sightseeing Tours include Hotel Pickup: Private Willamette Valley Wine Tour from Portland Private wine tour with local Sommelier. Private Tour at The Hood-Columbia Loop: Timberline, Orchards, and Waterfalls Private Northern Oregon Coast Day Trip Private Willamette Valley Wine Tour View all Tours with Hotel Pickup →

Q: Got any more Oregon trip ideas?

We sure do. Check out our curated lists of hand-picked Oregon Tours. Top 10 Oregon 2026 Senior-friendly tours Oregon The best tours and activities for culture lovers in Oregon Top Day Trips from Oregon Things to do in Oregon this summer View all Oregon Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Oregon?

Based on our sales data over the past year, the most popular styles of tours and activities in Oregon are: Oregon Luxury & Special Occasions Oregon Luxury Tours Oregon Tours & Sightseeing Oregon Sightseeing Tickets & Passes Oregon Attraction Tickets View all tour styles in Oregon →

Indulge your senses and savor the finest wines on our Willamette Valley Full-Day Wine Tour from Portland! This unforgettable journey promises a day of delight, …More

Portland, USA

Willamette Valley Full-Day Wine Tour from Portland

Indulge your senses and savor the finest wines on our Willamette Valley Full-Day Wine Tour from Portland! This unforgettable journey promises a day of delight,...

7 hours Hotel pickup offered

from
$490

Custom Willamette Valley Wine Tours from The Allison Inn and Spa

Are you staying at THE ALLISON INN & SPA? This high-end tour offering was custom designed to take guests from the Allison to small family …More

Portland, USA

4.9 (10)

Custom Willamette Valley Wine Tours from The Allison Inn and Spa

Are you staying at THE ALLISON INN & SPA? This high-end tour offering was custom designed to take guests from the Allison to small family...

6 to 9 hours Hotel pickup offered Free Cancellation

4.9 (10)

from
$375

Private Tour in Central Cascades with Photoshoot

Choose either to explore around Mt. Bachelor and drive up the Cascade Mountain Lakes Scenic Highway or the Three Sisters Mountains including Three Creeks Lake …More

Bend, USA

5.0 (1)

Private Tour in Central Cascades with Photoshoot

Choose either to explore around Mt. Bachelor and drive up the Cascade Mountain Lakes Scenic Highway or the Three Sisters Mountains including Three Creeks Lake...

3 to 4 hours Hotel pickup offered Free Cancellation

5.0 (1)

from
$365

Visit, explore and capture the best photo spots Bend and Central Oregon have to offer. Grab your camera and head out with one of our …More

Bend, USA

5.0 (1)

Private Full-Day Photo Tours

Visit, explore and capture the best photo spots Bend and Central Oregon have to offer. Grab your camera and head out with one of our...

7 hours 30 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$360

Private - Willamette Valley Wine Tour From Portland (tasting fees included)

The Northern Willamette Valley is just an hour’s drive from the Portland metro area. This close proximity to Portland creates a perfect opportunity for a day …More

Portland, USA

5.0 (12)

Private - Willamette Valley Wine Tour From Portland (tasting fees included)

The Northern Willamette Valley is just an hour’s drive from the Portland metro area. This close proximity to Portland creates a perfect opportunity for a day...

7 hours 30 minutes

5.0 (12)

from
$285

Willamette Wine Tour from Newberg (Tasting Fees Included)

Do you want to taste the best wines in Willamette Valley? Our custom private tours are designed to take couples and groups of friends deep …More

5.0 (37)

Willamette Wine Tour from Newberg (Tasting Fees Included)

Do you want to taste the best wines in Willamette Valley? Our custom private tours are designed to take couples and groups of friends deep...

6 to 9 hours Hotel pickup offered Free Cancellation

5.0 (37)

from
$239

Winter Focused Willamette Valley Wine Tour (Tastings Included)

Are you looking for the romantic, quaint or cozy tastings rooms in Willamette Valley, but also want to experience some of the best boutique wineries …More

5.0 (2)

Winter Focused Willamette Valley Wine Tour (Tastings Included)

Are you looking for the romantic, quaint or cozy tastings rooms in Willamette Valley, but also want to experience some of the best boutique wineries...

6 to 9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$239

Private Wine Excursion Willamette Valley, Oregon - Wine Tour

Gone are the days of choosing between a drowsy shuttle bus driver or the self-proclaimed expert viticulturalist to guide your journey through Oregon wine country. …More

Portland, USA

5.0 (62)

Private Wine Excursion Willamette Valley, Oregon - Wine Tour

Gone are the days of choosing between a drowsy shuttle bus driver or the self-proclaimed expert viticulturalist to guide your journey through Oregon wine country....

7 hours Hotel pickup offered Free Cancellation

5.0 (62)

from
$230

Private Back-Country Distillery, Brewery, or Pub Tour

The perfect sanctuary for men to escape the toils of daily life, fill their gullets with fine crafted spirits and brews, and beat their chests …More

Portland, USA

5.0 (4)

Private Back-Country Distillery, Brewery, or Pub Tour

The perfect sanctuary for men to escape the toils of daily life, fill their gullets with fine crafted spirits and brews, and beat their chests...

8 hours Free Cancellation

5.0 (4)

from
$230

Spend an entire day traveling through Hells Canyon and experience wildlife, swim in the fresh water, visit our historical sites and museums and more! This …More

4.9 (14)

Full Day Jet Boat Tour in Hells Canyon

Spend an entire day traveling through Hells Canyon and experience wildlife, swim in the fresh water, visit our historical sites and museums and more! This...

5 to 6 hours

4.9 (14)

from
$219

Visit, explore and capture the best photo spots Bend and Central Oregon have to offer. Grab your camera and head out with one of our …More

Bend, USA

5.0 (1)

Private Half-Day Photo Tours

Visit, explore and capture the best photo spots Bend and Central Oregon have to offer. Grab your camera and head out with one of our...

4 hours 15 minutes Hotel pickup offered Free Cancellation

5.0 (1)

from
$200

Private - Mt Hood & Columbia River Gorge Waterfalls Tour From Portland

Join an intimate, Oregonian-led Private tour of the Columbia River Gorge and Mt Hood with Portland, Oregon's original tour and adventure company. Your seasoned, local …More

Portland, USA

5.0 (2)

Private - Mt Hood & Columbia River Gorge Waterfalls Tour From Portland

Join an intimate, Oregonian-led Private tour of the Columbia River Gorge and Mt Hood with Portland, Oregon's original tour and adventure company. Your seasoned, local...

9 hours

5.0 (2)

from
$200

Eugene area Waterfalls & the McKenzie River in a Tesla

Explore Oregon's natural beauty on this McKenzie River tour, featuring riding in style with a Tesla. Enjoy a scenic 1.25 mile hike with stunning views …More

5.0 (1)

Eugene area Waterfalls & the McKenzie River in a Tesla

Explore Oregon's natural beauty on this McKenzie River tour, featuring riding in style with a Tesla. Enjoy a scenic 1.25 mile hike with stunning views...

4 to 5 hours Free Cancellation

5.0 (1)

from
$200

Curated Wine Country Experiences Full Day Tour

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings …More

Portland, USA

5.0 (1)

Curated Wine Country Experiences Full Day Tour

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings...

7 to 8 hours Free Cancellation

5.0 (1)

from
$200

US West National Parks GPS Audio Tour Bundle (33 Tours)

Embark on an epic journey through the US West with this self-guided driving and walking audio tour bundle! Explore the wonders of Arches, Bryce Canyon, …More

Crater Lake National Park, USA

US West National Parks GPS Audio Tour Bundle (33 Tours)

Embark on an epic journey through the US West with this self-guided driving and walking audio tour bundle! Explore the wonders of Arches, Bryce Canyon,...

3 to 4 hours Free Cancellation

from
$200

Wine History Tours: Private Willamette Valley Wine Tour

Willamette Valley is world-class wine country — but the best way to taste it is with someone who can tell you why it matters. On …More

5.0 (29)

Wine History Tours: Private Willamette Valley Wine Tour

Willamette Valley is world-class wine country — but the best way to taste it is with someone who can tell you why it matters. On...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$199

This is the only commercially available scenic tour on this section of river. You will learn the rich history of the area going back to …More

Portland, USA

5.0 (13)

Guided Jetboat Tour for Six -Private

This is the only commercially available scenic tour on this section of river. You will learn the rich history of the area going back to...

3 to 4 hours Free Cancellation

5.0 (13)

from
$195

Enjoy a private photo tour to experience and photograph the clear night sky of the High Desert. Very flexible tours start at your preferred time with …More

Bend, USA

5.0 (8)

Night Sky Private Photo Tour

Enjoy a private photo tour to experience and photograph the clear night sky of the High Desert. Very flexible tours start at your preferred time with...

3 hours Hotel pickup offered Free Cancellation

5.0 (8)

from
$187

Private Mt Hood Waterfall Tour with Lunch and Wine included

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by …More

Portland, USA

5.0 (2)

Private Mt Hood Waterfall Tour with Lunch and Wine included

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by...

8 to 9 hours Hotel pickup offered Free Cancellation

5.0 (2)

from
$175

Try to wipe the smile from your face as you experience an electric bicycle while enjoying a sensory overload of smells, tastes and sights. This …More

Portland, USA

5.0 (3)

Tasting the Gorge by Ebike

Try to wipe the smile from your face as you experience an electric bicycle while enjoying a sensory overload of smells, tastes and sights. This...

4 hours Free Cancellation

5.0 (3)

from
$150

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Oregon Private Sightseeing Tours?

What are the best kid-friendly options for Oregon Private Sightseeing Tours Tours?

Which Oregon Private Sightseeing Tours have Instant Confirmation?

Which Oregon Private Sightseeing Tours have Free Cancellation?

Oregon Private Sightseeing Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Oregon Private Sightseeing Tours have Hotel Pickup?

Got any more Oregon trip ideas?

What are the most popular styles of Tours and Activities in Oregon?