Top Portland Holidays

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

The Northern Willamette Valley's close proximity to Portland creates a perfect opportunity to join others on a small group public tour of Oregon’s wine country with Sea to Summit, Portland Oregon's original tour and adventure company.  Experienced, knowledgeable guides, providing fun and informative tours with unparalleled customer service, while operating the nicest and most comfortable, custom equipped 4x4 Mercedes-Benz vehicles in Portland’s tour industry. We set an itinerary with outstanding wine, great hospitality, and beautiful scenery with wine tasting fees included – all the keys to creating a unforgettable Willamette Valley Wine Tour for our clients... Created, owned and operated by native Portland Oregonian's, since 2001

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.

Visit Mt. Hood and the Columbia Gorge, with a couple of stops for wine tasting along the way, with this full-day tour. You'll visit Multnomah Falls, the Columbia Gorge's most famous attraction, hang out at Mt. Hood's historic Timberline Lodge, and pay a visit to two different wineries to taste Gorge-produced wine. There will be a hosted lunch on tour and a glass of wine at one of the wineries included. You will also be able to purchase beverages at your leisure during winery visits.

Discover Oregon's world famous wine region known as Willamette Valley and experience the best pinot noir, chardonnay, rose and other varietals guided by local wine lovers on this 8 hour tour. An excellent trip for new and seasoned wine lovers, a romantic weekend, or last minute vacation with your friends. Gain an inside perspective about the growing region, the winemaking process and the history of this valley. Expect to be pampered, entertained, and truly have a memorable trip in Oregon's Wine Country. This is a joinable small group tour for 2 persons or more. We will explore 3 of the finest vineyards in the valley and do a sit down lunch at our favorite establishment or vineyard lunch pairing. Proceed to check availability to see your exact price for the group size, we will handle all route planning and reservations on your behalf and offer door to door pickup and dropoff.

Join this walking pub tour and learn about the unbelievably weird people and events that take place in Portland. Topics include: UFO sightings, Bigfoot, cults, an exploding whale, beard competitions, hijackings, hipsters, protests and more. Our expert local tour guide will regale you with wild (but true!) stories about our beloved city. If you’re visiting Portland and want to see the city from a local’s perspective, we’ve got you covered. The tour is located outside of the downtown business district in a vibrant, walkable neighborhood. We stop at 3 funky pubs that are off the beaten path, away from overcrowded tourists traps. These local favorites have oddities covering the walls, unique artwork and one even has a 12 foot tall skeleton! Skip the places in all the books and come let us show you our favorites places. The tour explores the Hawthorne neighborhood, known for its abundant artwork, dive bars, food carts, and vintage stores.

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.

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.

From fiery deaths to watery graves: In this 1.5 mile cemetery walking tour, we weave what we know of the peoples who lived here for millennia with verifiable stories of recent centuries. We can only guess, based on our psychics’ readings and eerie coincidences we have observed, where people here before us feared to walk and canoe at night. As a wise person wrote, every story ends as a ghost story. Our ghosts are legion. We now call it Oregon; “ourigan” was ancestral home to hundreds of thousands. They have left a darkness here, expressed with stories from the earliest days of our written history to modern times. Starting with early disasters, we will tell ghost stories we have collected, from fiery deaths to those in the waters of nearby river; from self-inflicted to deaths brought by the state or a rich man’s guilt. Our route takes us through the inner eastside, where more of Portland’s disasters have happened than any other part of the city & where many early settlers are buried.

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.

The Oregon coast is one of the most majestic geologic formations that was formed by lava flows millions of years ago. We depart to the coast and have lunch in the charming town of Cannon Beach and do hiking and exploring on the coast. Explore the majestic Oregon coast, view the amazing Haystack Rock formation, and during low tide gaze at starfish and clams. We will also explore Oswald State Park for lite trail walking and see the stunning cliffs of Manzanita point. This is a joinable small group tour for 2 persons or more, door to door service. Please dress for the season, expect a full day beginning 10am and back to Portland by 6pm.

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.

This is an amazing way to see the most spectacular Oregon wonders like Multnomah Falls, Vista Point driving thru the breathtaking and rugged beauty of the Columbia Gorge. We will see various waterfalls like Multnomah Falls, Latourell Falls , a lunch stop in the quaint historic downtown Hood River, a wine tasting stop at one of the amazing Vineyards in the Columbia Gorge AVA. This is ideal if you want to do some scenic, nature stops with light trail walking and also enjoy a vineyard stop, its absolutely the most amazing way to spend 8 hours.

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

Experience the best of Oregon's nature and wineries in a single day on a small-group tour. The adventure begins with a comfortable transfer from your Portland accommodation to Silver Falls State Park. Here, you’ll follow your guide on a moderate 5.7-mile (9.2-kilometer) hike along the Trail of Ten Falls. Then, enjoy tastings at two boutique wineries (own expense) and a freshly prepared picnic lunch.

Combine a fun night out with ghostly tales of the city during this Portland Haunted History Pub Crawl Experience. This pub crawl takes you to multiple pubs, including Kells Irish Restaurant and Pub and Shanghai Tunnel Bar as you pass by city highlights such as the Benson Hotel. Hear spooky stories of ghosts and paranormal activity from your guide during the evening.

Explore Oregon's world famous wine country known as the Willamette Valley and experience the best Pinot Noir, Pinot Gris, Rose, Chardonnay and other varietals guided by local wine lovers with enough time to stop for a nice sit down lunch. Gain an inside perspective about the growing region, the winemaking process and the history of this valley at each vineyard during your tasting. Expect to be pampered, entertained, and truly have a memorable trip in Oregon's Wine Country. This is limited to 10 people in a small joinable group, but usually much smaller in our modern and comfortable 15 passenger vans.

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.

Go bar hopping with a local resident with this casual, friendly walking tour of Portland's local bars. Your enthusiastic local guide will take you and your group to some of his favorite local haunts, with a heavy focus on interacting with locals and checking out the city's neighborhood vibes.

Hear fascinating history along the scenic route, visit stunning waterfalls and historic buildings, marvel at unparalleled craftsmanship and timeless artwork, visit mountains and wineries. Among the sights we will see are Timberline Lodge on picturesque Mt. Hood, with 4-stories of heavy timber, built by artisans for the Works Progress Administration. Roll through quaint Hood River Valley, where we will visit two boutique wineries and a local produce stand. Travel through astounding Columbia River Gorge and feel the spray of majestic Multnomah Falls, where you can cross a stone bridge halfway up the waterfall and visit a rustic gift shop in the historic inn. Lunch from a gourmet food cart is included. Wine tastings can be purchased for an additional fee during your visit, if desired. So many beautiful sites to see and stories to hear! Sip, sip, hooray! Your tour guide is a seasoned professional, who delivers a dynamic tour with humor and insight.

Wine-lovers rejoice, this one’s for you! Enjoy a full year of wine-tasting experiences and exclusive discounts on purchases from more than 450 wineries across the United States’ renowned wine-making regions. With convenient access to a concierge service that helps you get the best value out of the priority pass, your year of wine-tasting and vineyard tours is as easy as raising a glass.

Oregon's Willamette Valley is known for its Pinots and it's a fantastic place to go wine tasting, provided you leave the driving to someone else. This private tour will take you to three wineries, where you'll sample wine and learn about the ins and outs of Pinot production. You'll be able to sample safely, knowing that someone else will be doing the driving.

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.