Top Oregon Private and Luxury - page 3

Get a prime view of the sunrise over the Portland skyline with this experience. Your guide will take you up to the hilltop Oregon Health Sciences University to catch the city's Aerial Tram. After taking in sunrise views while you dine on a breakfast of coffee and donuts, you'll hop aboard the tram and take a ride down to river-level, taking in views of the skyline along the way.

Immerse yourself in Portland's charm on this small-group half-day city tour that blends top sights with scenic beauty. Ride through lush parks, vibrant districts, and historic landmarks, including the International Rose Test Garden and Pittock Mansion. Enjoy sweeping views from the Portland Aerial Tram and learn how a modest fishing village became “Bridgetown.” With a local guide and comfortable transport, you’ll see why Portland captures the hearts of visitors worldwide.

Experience the unrivaled beauty of the Columbia River Gorge, Cascade Mountain Range, and Mount Hood—and see them all in one hassle-free, time-saving excursion—on this full-day tour from Portland. In the comfort of a luxury vehicle, travel with just your guide and a small group for company. Enjoy a guided tour of the Gorge’s top destinations, including Vista House, Multnomah Falls, Timberline Lodge, Hood River, and more.

Download GuideAlong’s self-guided driving audio tour of the best of Oregon’s Mount Hood Loop. Discover the dramatic Multnomah Falls, scenic roads through the Columbia River Gorge, lush hiking trails, alpine lakes, and the historic Timberline Lodge. Along the way, you’ll follow the Mount Hood Scenic Byway, cruise the Hood River “Fruit Loop” farm trail, and enjoy breathtaking mountain views. The expert narration along the way is an ideal companion for an unforgettable Oregon road trip. Enjoy the freedom to explore offline at your own pace, spending more time at places that interest you and bypassing any that don’t. Stories, tips, and directions play automatically based on your location Travel at your own pace Tour offline using GPS. No cell service or WiFi is needed Suggested itineraries for half, full, or multi-day use No time limits or expiry, and free updates Like having a tour guide along for the drive Purchase one tour per vehicle.

This is not a tiny-spoon tasting tour. At every stop, guests sample every available flavor and receive a full scoop per person — all included in the ticket price. There’s no choosing just one flavor, no standing in lines, and no additional purchases. The entire experience is fully hosted by entertaining local guides who handle ordering, keep things moving, and make it fun. You’ll enjoy laughs, insider food recommendations, and a relaxed walk through the heart of Portland. With multiple flavors plus full scoops at each stop, many guests say this feels closer to an almost all-you-can-eat ice cream crawl than a traditional food tour — just without the chaos or rushing. Created by Portland locals with a genuine love for ice cream and their city, this tour is designed to be generous, easy, and unforgettable — perfect for families, visitors, and serious ice-cream lovers.

Taste your way through Oregon’s renowned wine scene right in the heart of Portland! Try a variety of wine varietals and savor delicious bites, all while exploring the vibrant Pearl and Slabtown neighborhoods. What makes this wine tour special? We’ve met with the wine experts themselves and did all the research for you, so the tastings and snacks are curated and included. You’ll try 10+ wines at two winery tasting rooms plus one wine bar, including a variety of white, rosé, and red, and snack small bite pairings. Highlights: - Taste 4 Oregon wines paired with artisan popcorn at an approachable winery while learning why Oregon wine is special. - Explore 2 trendy Portland neighborhoods, blending old and modern architecture with rich history. - Dine on bruschetta paired with wine at a family-run winery. - End your evening sipping Bordeaux in a secret wine bar where you might just uncover a hidden surprise. - Learn from your tour guide and wine experts. *This tour is 21+ ONLY.

Get out of the big city and explore the stunning beaches and beautiful towns along Oregon’s northern coast on this full-day, small-group tour from Portland. Visit the charming towns of Manzanita and Cannon Beach—home of the famous Haystack Rock—browse antique shops and art galleries, and stop at several beaches to maximize your time at the Oregon Coast.

See Portland like a local—by bicycle—with this guided tour. Your guide will take you on an eight- to 11-mile ride through town, past beautiful neighborhoods filled with flowers and across the river via the pedestrian- and bicycle-only Tilikum Bridge towards downtown, with a stop at a local donut shop for some sugary fuel along the way.

Take in the sights of the Northern Oregon Coast without having to keep your eyes on the road with this small-group tour from Portland. You'll pay a visit to the iconic Haystack Rock, stop for lunch in Cannon Beach, known for its cute art galleries and restaurants, and take a short hike in seaside Ecola State Park, all with a local driver/guide to lead the way.

Visit the Columbia Gorge, easily one of Oregon's most scenic spots, with this intimate half-day tour from Portland. You'll make plenty of stops along the way, with the chance to take in the views from the aptly named Vista House and the Portland Women's Forum State Scenic Viewpoint. You'll also visit Horsetail Falls, Latourell Falls, and the most famous waterfall of them all, Multnomah Falls, the tallest waterfall in the state.

Oregon’s Willamette Valley is known for its fantastic wine, and while it’s easy to get to from Portland by car, driving yourself means limiting your consumption. This small-group tours includes the services of a driver so you can taste wine without worrying about designating a driver, showcasing off-the-beaten-path wineries that you might otherwise miss.

Discover the waterfalls and natural attractions along the Historic Columbia River Highway at your own pace with a hop-on hop-off trolley pass. The trolley's comprehensive route includes stops at Benson Bridge, Horsetail Falls, and Ainsworth State Park. Spend as much time as you like at each location, then catch the next available bus when you're ready to head to the next stop. Along the way, learn about local geography and history.

Immerse yourself in waterfall hiking in one of the most unique geologic formations in Oregon! Over the course of the three hours we are in the canyon, we will discovering South Falls' stunning amphitheater and history as the centerpiece of a failed attempt to become Oregon's first National Park. From here we will descend into the up-and-down trails that make up the gorgeous canyon, encountering century-plus-old trees, wildflowers in season, mosses, lichens, and mushrooms and a variety of fantastic rock formations. We will experience up-close encounters with some of the state's most unusual and impressive waterfall formations. On this hiking experience we will explore 4-6 waterfalls and enjoy snacks with the option to purchase a light breakfast or lunch from the cafe. Our hike will be between three and eight miles (5 - 13 km) depending on group energy and desire.

Located east of Portland, the Columbia River Gorge is home to rugged cliffs, and majestic waterfalls. On this convenient half-day tour, travel outside the city to the gorge to see several waterfalls, including Multnomah Falls, one of the tallest waterfalls in the country, and Latourell Falls, as well as sweeping views from Vista House.

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. Your tour also includes pickup from over 60 hotels in Portland and a private or small-group option.

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.

Combine two of Portland's quintessential experiences—cycling and food carts—with this small-group guided tour. You'll visit Portland's first major food cart pod, Cartopia, cycle through the flower-filled neighborhoods of Ladd's Addition and Hawthorne, and make a stop at the Scout Beer Tap House, all with a local guide to show you the way.

Immerse yourself in the beauty and bounty of Willamette Valley's renowned wine country on this full-day, small-group tour from Portland. Perfect for all levels of wine enthusiasts—from newcomers to connoisseurs—this tour whisks you to three or four top-rated vineyards. Sample a range of varietals (tasting fees own expense), enjoy a picnic lunch, and benefit from door-to-door service.

Soar over the Columbia River Gorge on a sightseeing flight that takes you from Portland to the scenic gorge. Ideal for visitors who are short on time but don’t want to miss any of the highlights, these 20 minutes of flying time show you more than you could see on a full-day ground excursion. Plus, the aerial view provides great photo opportunities.

Experience Oregon from the sky with this aerial tour above some of the state’s most dramatic scenery. This small-group flight takes you above the Columbia River Gorge, over the Mt. Hood National Forest, past Multnomah Falls, and back to the city. Note: depending on the weather, the pilot may have to alternate the route.

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.

Visit the northwestern Oregon Coast without renting a car by booking this small-group tour from Portland. Your local guide will be on hand to provide commentary as you make your way along the Pacific Coast, and can help you and the other members of the group decide on what stops you want to make along the way.

Experiences both Portland’s rugged outdoors and renowned wine scene on this small-group tour. Visit the Columbia Gorge National Scenic Area where you see waterfalls, admire the Cascade Mountain Range, and look out for bald eagles and osprey. Then explore Hood River and stop at a variety of boutique wineries to sample locally produced wines including the much talked about Oregon Pinot Noirs.

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