Top Portland Private Sightseeing Tours

Experience Oregon from the sky with this aerial tour above some of the state’s most dramatic scenery. This flight for up to three people will take you above the Columbia Gorge, over the Mt. Hood National Forest and back. Note that prices are for the entire plane ride, so bring a couple friends and make a day of it.

Explore the eerie side of Old Town with this haunted pub tour in Portland. Learn about some of the city's scary history as you walk through 19th-century buildings. Sample local beers as you hear about Portland's era of kidnapping, gangs, prostitution and opium dens.

Discover Mount Saint Helens from a unique vantage point on a private flight tour from Troutdale. Once airborne, soar over the Colombia River Gorge and Portland. Have your camera ready as the plane flies above and around Mt. Saint Helens' crater and see the destruction from its 1980 eruption. Note: The flight route is dependent on weather and may change last minute.

Go wine tasting through the Willamette Valley on your own terms, with an expert local guide with over three decades of experience. With this tour, you'll visit around four estate wineries, with the option to customize your tour to suit your preferences. You'll also have the chance to stop for an included picnic lunch along the way, which you can enjoy during one of your tastings.

If you’ve never flown on a private plane before, this 20-minute ride over the Columbia River Gorge will be an unforgettable experience and a thrilling overview of the natural beauty of the Pacific Northwest. Your knowledgeable pilot will take you east through the Gorge toward the Vista House viewpoint, past the waterfalls and cliffs of the Gorge.

Head out to the Columbia River Gorge for half a day of visiting cascading waterfalls and scenic overlooks with this tour from Portland. You'll visit Multnomah Falls, the highest waterfall in the state, as well as lesser-known falls throughout the region. You'll also have the chance to take mini-hikes in the area to get better views of waterfalls and the surrounding scenery.

Experience the best of Willamette Valley wine country on a guided wine-tasting tour from Portland. With a small group of fellow wine lovers, spend half a day visiting three handpicked wineries such as Colene Clemens Vineyards and Montinore Estate. Meet local vintners and sample award-winning varietals while marveling at Oregon’s stunning countryside.

Experience highlights of the Portland area on this full-day sightseeing tour, including the blossoming food cart culture, diverse neighborhoods, Pioneer Courthouse Square, and the unspoiled beauty of the Columbia River Gorge. Immerse yourself in a guided tour of Portland’s fascinating history and quirky contemporary culture.

Escape the hustle and bustle of the city for the day on this guided tour to Multnomah Falls and the Columbia River Gorge Waterfalls. Travel along the historic Columbia River Highway National Scenic Byway and stop at the magnificent falls of Multnomah, Latourell, and Bridal Veil.

Immerse yourself in the beauty and bounty of Willamette Valley wine country on this full-day tour from Portland. Perfect for all level of wine enthusiast – from newcomers to connoisseurs – this 7.5-hour trip offers the insight of expertly trained guides and visits to 3-5 vineyards to sample unique varietals including renowned pinots, chardonnays and rieslings. Tasting fees are not included.

Immerse yourself in the beauty of Columbia River Gorge on this full-day trip from Portland to Mount Hood! With your small group, take a guided tour of such iconic Oregon destinations as Multnomah Falls and the famous Timberline Lodge, and enjoy lunch in the charming city of Hood River.

Species seen nowhere else in the world, dramatic basalt lava flows nearly a mile deep, and some of the world’s most beautiful waterfalls are a few of the sights that await you on this tour. Come experience the grandeur of the Columbia River Gorge, one of the United States’ most photographed Natural Scenic Reserves. We will drive along the oldest scenic highway in the US, stopping at sweeping viewpoints, flowing falls, a historic lodge, and the famed Bonneville Dam Sturgeon viewing center.

Combine hiking and bicycling on this small-group tour of the Columbia River Gorge, ideal for active travelers. After a minivan ride from Portland to the Gorge, you'll hop on your bike and start exploring, stopping at the Vista House, Bridal Veil Falls, and Multnomah Falls along the way. You'll also visit Latourell Falls, where you'll take a hike al long a 2.1-mile loop trail up to the lower falls.

Experience the unrivaled beauty of the Columbia River Gorge, Cascade Mountain Range and Mount Hood on this full-day trip from Portland. In the comfort of a luxury vehicle, enjoy a guided tour of the Gorge’s top destinations, including dramatic waterfalls, the Bridge of the Gods, Hood’s Timberline Lodge, and the charming city of Hood River.

Immerse yourself in immaculate Pacific Northwest scenery—and indulge in some special beverages along the way—on this private tour by e-bike. Meet your guide in Hood River, get acquainted with your bike, and then zip off. You’ll go for a 7-mile (11 -kilometer) ride along the Historic Columbia River Highway State Trail, will visit a local winery and brewery for tastings, and can opt to finish with a short hike.

Exclusive! Private! Customized to your desire! - Chauffeured in a classic Rolls-Royce, the only one in Portland, a brand that sets the highest standard of luxury, comfort, and elegant. Complete hand built by the Brits! - Travel and arrive in style! Make every head turns, wherever you go. - Taste some of the finest wines that second to none in Oregon, and it is included in the package! - Make the deal sweeter with complimentary charcuterie board with selection of cured meats, stone-ground mustard, crisps. - Flexible to extend beyond 4 hours or customize the itinerary to visit any wineries that you already have reservations.

Spend an afternoon exploring Portland with a guide on this private tour. You’ll visit downtown Portland's Pioneer Courthouse Square, the trendy Pearl District, the International Rose Test Garden, and Tilikum Crossing, the biggest car-free bridge in the country. You will then head out to Oregon City, a short drive from town, to see Willamette Falls and ride on the 130-foot-tall Oregon City Municipal Elevator.

Explore Portland from above on a private flight. See the city’s skyline and natural landscapes as you fly low over the Columbia River Gorge, and industrial cityscapes. See Bridgetown from a new perspective as you soar through the sky and hear historical and geographical insights from your pilot. The small-lightweight plane can hold 1-3 passengers plus the pilot. Forget about traffic and see the city from the sky on an airborne adventure.

Take a scenic cruise along the Willamette River while you learn about Oregon's history. Your captain will take you on a 44-mile journey, showing you historic attractions such as the Wheatland Ferry Crossing, which first began operations back in 1845. This tour is totally private and up to six passengers can be accommodated.

Portland is home to a buzzing array of neighborhoods, historical highlights, and natural attractions—and this private, half-day tour makes for a seamless introduction. Pick between morning and afternoon tour times and hop aboard your luxury, air-conditioned vehicle. You’ll visit the International Rose Test Garden and Pittock Mansion, and will drive past landmarks like the Oregon Zoo, Portland Art Museum, and more as you explore the city’s neighborhoods.

Explore the northern stretches of the Oregon Coast with a local guide on this private, customizable tour from Portland. You'll get to ride along the Pacific Coast Scenic Byway, take a hike through old-growth forest, and stop at one or two local towns or attractions of your choosing along the way.

See Oregon’s infamous waterfalls from above on a private airplane tour through the Columbia River Gorge. Get 360-degree views as you soar over the Vista House, Booneville Dam, the Bridge of the Gods near Cascade Locks, and more. This private experience allows you to customize your itinerary to fit your preferences. 

Enjoy a private tour of Portland waters on an up to 90-minute sailing cruise. Bring up to five others on a leisurely meander along the Willamette River, choosing between an up river journey to the forested Elk Rock Island or a ride taking in the city skyline and bridges. Relax, unwind and simply savor postcard views as well as time with your friends and loved ones. You can enjoy BYO snacks, beer and wine to savor while soaking in the surrounding atmosphere.

During this walking tour you'll discover Portlands's unique character and rich history. Led by a knowledgeable guide, you'll explore charming streets, picturesque plazas, and bustling public spaces, learning about the city's role as a hub for trade and transportation.Experience Portland's commitment to sustainability as we pass through green spaces and highlight the city's innovative environmental initiatives. Along the way, we'll share fascinating stories and fun facts about Portland's past and present, including its cultural significance as a center for the arts.This tour will include stops at hidden gems and local favorites. The guide will provide insights into the city's vibrant culture and  share local tips on the best places to eat, drink, and explore. Whether you're a first-time visitor or a long-time resident, this walking tour is the perfect way to discover the best of downtown Portland.