Top Portland Private Sightseeing Tours

Visit the top attractions in the Columbia River Gorge National Scenic Area and Mt. Hood National Forrest on this day trip from Portland. After spending the morning chasing waterfalls and marveling at 500 pound fish at Bonneville Fish Hatchery, enjoy a 1-hour lunch in historic downtown Hood River. After lunch, we will visit a vineyard in the region for some amazing wine tasting followed by a drive over halfway up the side of Mt. Hood to explore Timberline Lodge

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.

See the largest waterfall in the Northwestern United States. Explore Portland's downtown waterfront, urban wildlife, and beautiful bridges from the water. The Willamette river is a beautiful and calm waterway with a storied history and amazing nature up and down her banks!

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 enjoy strolling in Lan Su Chinese Garden.

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 Domaine Serene. 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 up to 3 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, and a historic lodge.

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.

Experience the diversity of flavors out of the Willamette Valley on this wine-tasting tour from Portland. In a small group, wind through the verdant hills of Portland’s surrounding wine region en route to three select vineyards. Your tasting adventure includes unique wine flights, snacks and a behind-the-scenes look at local viticulture.

Upon arriving in Portland International Airport, avoid lugging around your baggage and waiting in line for a taxi. Book this private airport transfer and get to your destination quickly and in comfort. Transfer is available to your hotel in Portland, Beaverton, Lake Oswego or Tigard.

Visit Mount Hood and Oregon's most celebrated waterfall on this private experience from Portland. You'll start with a drive out to Multnomah Falls in the Columbia River Gorge, before heading to Hood River for lunch, shopping, and a drive through the “Fruit Loop” agricultural region. Before heading back to Portland, you'll get the chance to stop at Timberline Lodge at Mount Hood.

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.

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.

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 River 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.

Embarking on a 1.5 mile (2.4 km) walk through the heart of downtown Portland offers an immersive exploration into the city's rich tapestry of history, culture, and innovation. Portland unfolds its stories through a series of iconic landmarks, bustling public squares, and artistic expressions that color its streets. You'll encounter not just the narrative of its past, but the living, breathing essence of what makes Portland beloved. Admire vibrant murals and sculptures that punctuate the cityscape. Witness the symbiosis between architecture and environment. Even the smallest park in America claims its fame among the city's green spaces. We'll share how Portland changed from a forest, to the wild-west "stumptown," to the vibrant "little" city it has become. This walk isn't just a physical journey but a passage through time, revealing how Portland's innovative spirit has shaped its identity from historic times to the present day. Each tour may vary, depending on your guide.

Take in the sights of the Oregon Coast without worrying about driving with this private tour from Portland, Your driver will pick you up at your accommodations and take you west to the coast, known for its unusual mix of forest and sandy beaches. You'll get plenty of chances to stop along the way at some of the region's prettiest viewpoints and cutest towns.

Exclusive! Private! Customized to your desire! - Minority owned and operated - Chauffeured in a classic Rolls-Royce, as seen in Netflix show The Crown, a brand that sets the highest standard of luxury, comfort, and elegant. Completely 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 the tasting fee is included in the package - Wineries including Domaine Serene, ROCO, Adelsheim, and other best quality wine makers in the region. Note: Starting 2024, we no longer bring guests to Sokol Blosser because they are not friendly to minority owned tour business. - Make the deal sweeter with one complimentary snack, e.g. charcuterie board, meatballs, etc. - Flexible to extend beyond 4 hours or customize the itinerary to visit more wineries

Explore the Willamette Valley, the largest wine-producing region, on this private tour designed with large groups in mind. You'll get the chance to visit three or four wineries and stop for an included lunch along the way, all with a guide/driver to help make your experience safe, fun, and informative.