Top Oregon Sightseeing Tours - page 6

Visit Mount Hood and many of the highlights of the Columbia Gorge in just one day with this private tour from Portland. You’ll visit Timberline Lodge on Mount Hood, four Columbia Gorge Waterfalls (including famous Multnomah Falls), and get the chance to stop by two wineries in the region, with lunch included along the way.

Escape to an island paradise without leaving PDX on this tropical happy hour cruise! Sip a delicious drink, take in the city sights, and catch up with old friends or meet new ones aboard Portland's only tiki-style river boat. Depending on the day, crew and crowd, vibes vary from lively and energetic to chill and relaxing. Come connect, take in the fresh air and celebrate a special occasion—or just life itself! At Island Style Charters, every day is a party. **Perfect for:** Happy hour • Celebrations • Work Groups • Travelers • Afternoon Dates • "Just because" **Highlights:** Tropical tiki boat • Downtown river views • Music, drinks & snacks available for purchase **Cruise Duration:** 1 hour **August:** 4:30 PM check-in, 5:00–6:00 PM cruise. **September & October times vary** Please review all booking details and communications carefully before your cruise.

Step aboard Portland's only tiki boat for a 1.5-hour river cruise blending laid-back island vibes, scenic city views, and playful onboard fun. Relax and take in downtown landmarks and iconic bridges, sip a drink, and enjoy the breeze as we cruise the Willamette. A lively host keeps the atmosphere fun with games like trivia and cornhole, plus chances to win prizes. Whether you're here to unwind, connect with family, meet new friends, or rediscover the city from the water, this cruise is designed to flow with the moment—a perfect mix of relaxation, socializing, and river adventure, all with unforgettable island style. Most cruises check in at 2:00 PM and cruise from 2:30–4:00 PM PT. Some departures check in at 12:00 PM for a 12:30 PM departure. The first 30 minutes of the 2-hour event window is for boarding. Please feel free to email directly with questions or to confirm your scheduled departure time.

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

Columbia Gorge and Mount Hood Private Day Tour Experience the Columbia River Gorge and Mount Hood in just one day with this private tour from Portland. You'll meet your driver downtown and head out to the Gorge, stopping to take in the views at Vista House and Multnomah Falls before continuing toward Mount Hood National. Here you'll get to visit the historic Timberline Lodge, right on the mountain, before heading back to Portland.

Escape the city for half a day—and explore the scenic highlights of the popular Columbia River Gorge—on this private tour. Pick between morning and afternoon start times, set off in a luxury Mercedes, and head into nature. You’ll discover stretches of the 74-mile (119-kilometer) highway, and immerse yourself in the Pacific Northwest scenery. Discover waterfalls like Latourell Falls and Multnomah Falls, admire Beacon Rock, stop at scenic viewpoints, and more.

Take a tour of the Deschutes River as it winds through and around the city of Bend, while riding your premium electric bikes. You will find yourself cruising along the river with your guide, enjoying the sights and sounds without breaking a sweat. Enjoy awesome scenery and wildlife, while your guide shares historic stories of Bend and the local area with plenty of opportunities to take pictures and ask questions.

See the highlights of Portland in just half a day on this private tour of Portland. You'll explore downtown Portland and the nearby NW 23rd shopping district, take in city views from the International Rose Test Garden and stroll through Lan Su Chinese Garden. If you come on a Saturday, you’ll visit the PSU Farmer’s Market.

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 at 2 -4 hand selected boutique and estate wineries. Our tours can be customized to fit your desires, whether you’re interested in gourmet food pairings, private luxury experiences, or special event packages. Enjoy our transparent pricing with no hidden fees and comfortable vehicle for a relaxing day in wine country. - Explore 3-5 boutique and estate wineries with expert guides - Tailored private luxury tours for couples and groups - Enjoy exclusive reserve tastings and artisan food pairings - Flexible half-day and full-day options available

Embark on an unforgettable journey with our exclusive vineyard, stable and historic Governor's farm house. Your tour begins with seamless pickup from the airport, your hotel, or anywhere along the Portland to Eugene, OR corridor. Dive into the charm of West Hills Vineyards, where your adventure begins at the stunning West Hills Stables—home to a state-of-the-art dressage facility and a remarkable collection of Classic Cars. Explore the scenic beauty of Holmes Gap Vineyard, and conclude your day with a delightful wine tasting and gourmet meal in the historic Oregon Governor's farmhouse, built in 1857. Don’t miss this chance to indulge in luxury, history, and world-class wines!

Our 2 hour guided snowmobile tours will take you throughout the Newberry National Volcanic Monument located in the heart of Central Oregon. The massive caldera of the Newberry Volcano, is the largest shield volcano in the Cascade Mountain Range. Our experienced guides will lead you to some of the areas natural wonders such as Paulina Lake, Paulina Falls, East Lake, The Big Obsidian Lava Flow, and weather permitting up to the summit of this 7,989-ft active shield volcano! On our two hour tours, you’ll enjoy world-class views and an endless variety of trails for all skill levels and rider abilities.

Discover Portland with our self-guided tour, exploring the quirky, creative, and fiercely independent city nestled between the snow-capped peaks of Mount Hood and the rugged Oregon coast. Begin at Pioneer Courthouse Square and wander into Powell's City of Books, the largest independent bookstore in the world, filling an entire city block with over a million volumes. Stroll the warehouses of the Pearl District, then ascend into the West Hills to experience the Portland Japanese Garden and the International Rose Test Garden with 10,000 rose bushes blooming beneath Cascade Range views. Cross the Willamette River on the Hawthorne Bridge to discover the murals and vintage shops of the Alberta Arts District. Explore the Lan Su Chinese Garden, taste legendary doughnuts at Voodoo Doughnut, and marvel at the Gothic arches of St. Johns Bridge in Cathedral Park. Beyond the city, visit Multnomah Falls — Oregon's tallest waterfall plunging 189 meters down a basalt cliff in the Columbia River Gorge.

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. Welcome to The Good Vibes Tour, we specialize in transporting you directly to the experts: the passionate artisans behind these exceptional Willamette Valley vintages. It all begins with The Vibe. Our drivers are adept at gauging the group and seamlessly adapting their interaction to enhance the collective; interacting as much or as little as adds to your experience. Then there’s our meticulously crafted luxury coaches. Far from your typical passenger van or conventional limousine, our transport evokes the ambiance of the Pacific NW; complete with an open and inviting floorplan, rustic wood accents, a simulated fireplace, and modern amenities like a coffee nook, Bluetooth music and optional karaoke. Take a photo/video tour of our fleet online and book your adventure!

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 and views of Tam MacArthur Rim. Learn about the natural landscape with a local photographer by Central Oregon's best scenic view points and get 15-20 high quality edited photos to remember your time here and the picturesque Cascade Mountains.

There's no better way to explore Portland than on bicycle, and with this private electric bike tour, you'll get to see the best of what this city has to offer, like a local! This tour is led by a former city spokesperson who knows the city inside and out. There will be plenty of stops along the way for photos and snacks, and special requests can be made in advance.

Our 4 hour guided snowmobile tours will take you throughout the Newberry National Volcanic Monument located in the heart of Central Oregon. The massive caldera of the Newberry Volcano, is the largest shield volcano in the Cascade Mountain Range. Our experienced guides will lead you to some of the areas natural wonders such as Paulina Lake, Paulina Falls, East Lake, The Big Obsidian Lava Flow, and weather permitting up to the summit of this 7,989-ft active shield volcano! On our four hour tours, you’ll enjoy world-class views and an endless variety of trails for all skill levels and rider abilities.

If you’ve flown around one mountain, you know how incredible it is. Now imagine flying around three for the most up close aerial view you can have! Experience up close details of Mt. St. Helens, Mt. Hood, and Mt. Adams on this air tour that takes you around these three iconic Pacific Northwest mountain peaks. On this flight tour, you’ll see these mountains in incredible detail, including overflying vast forests filled with lakes, creeks, rivers, valleys, and trees. This will be an experience you’ll never forget.

Explore the stunning Crater Lake National Park at your own pace with this self-guided driving tour. Experience the majesty of the deepest lake in the U.S. as you navigate the iconic Rim Drive, where GPS-triggered narration brings to life the park's geological wonders and rich history. Marvel at breathtaking views from scenic overlooks, hike to hidden trails, and uncover the legends of the Klamath people as you drive through this extraordinary landscape. With no groups and no schedules, enjoy the freedom to stop and explore at your leisure. - Self-guided tour featuring GPS-triggered narration for a personalized experience. - Discover key sights like Wizard Island, Phantom Ship, and stunning waterfalls. - Drive the 33-mile Rim Drive with breathtaking views around the caldera. - Duration of 3–5 hours, allowing ample time for exploration and hiking.

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on TripAdvisor, Google and Yelp for Private Tours & Group Tours. My commentary will give guests insider knowledge and our winery visits will give guests memorable encounters with winery staff. I can specialize the tour to suit your taste. I prefer wineries with amazing wine and beautiful views but, it's your choice. You can choose your wineries and can also pick them . Also, there are lunch choices to be made.

New for 2026! Experience Multnomah Falls the easy, comfortable, and budget-friendly way — without being packed into a crowded van. This full-day round-trip tour from Portland includes narrated motorcoach transportation and extended time to explore Oregon’s most famous waterfall at your own pace. Skip the stress of Gorge traffic, parking, and timed-entry permits. Instead of squeezing into a small van with limited views and little room, enjoy a spacious motorcoach with large windows, comfortable seating, easier boarding, and room to relax. The narrated ride adds local insight along the way, making the journey part of the experience. At Multnomah Falls, take photos, walk to the iconic Benson Bridge, visit the historic lodge, enjoy a snack or meal, browse the gift shop, or simply take in the scenery. Enjoy more space, better views, more comfort, and more time at the falls — all with trusted local and worldwide sightseeing operator Gray Line of Portland.

Solve a self-guided walking quest through Ladd's Addition, Portland's hidden architectural gem in the Southeast. Decode classic ciphers, hunt for landmarks, and explore a maze-like neighborhood with diagonal streets, five rose gardens, and over 100 historic homes. Use Questo app on your phone to follow 15 stops through Ladd's Addition: Seven Corners, Ladd Circle, the historic Hat Museum house, the East and West Rose Gardens, and hidden alleys. Solve riddles, decode A-to-Z ciphers, and find architectural details most visitors miss. Each chapter has its own puzzle and a real piece of Portland history, from the 1891 diagonal street plan to the bungalow and Craftsman homes that define Southeast Portland. Start anytime, pause whenever, and pick up where you left off. Bike-friendly: works on two wheels too. Perfect for architecture fans, repeat Portland visitors looking off the beaten path, families with curious kids, or anyone who wants to keep Portland weird.

Have only a single day in Portland and want to see it all? Take our Multnomah Falls & Rose City Tour and get the best of both. See Multnomah Falls, spending an hour there and then its back to Portland to see the sights you want to see on the Rose City Hop-On Hop-Off Trolley. A full day of touring at a reasonable cost.

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

Two park rangers warm quick-witted Quinn and old-soul storyteller Boone — narrate automatically by GPS as you drive the Historic Columbia River Highway, so your eyes stay on the road and the waterfalls, not a screen. You roll past seven waterfalls and the cliff-top Vista House while they unspool the Gorge's legends and lost history. Works fully offline — the Gorge has spotty signal. Buy once, keep it forever.