Top Oregon Holidays in 2026

Are you looking for the romantic, quaint or cozy tastings rooms in Willamette Valley, but also want to experience some of the best boutique wineries Willamette Valley has to offer? Our *Winter Special* wine tour is designed to get you to the handful of tasting rooms who offer world-class wines, amazing hospitality and also have the cozy fireplace ambiance to make your getaway memorable, restful or simply magical. On this tour, we will go to three wineries at a relaxed pace; or, if desired, four wineries at a fast clip. We will stop for lunch at one of the celebrated sandwich spots in the valley and your guide will join you for lunch. If wine by the fire is what you are after, then look no further!

Explore the stunning natural beauty of the Columbia Gorge with a unique blend of adventure and fine wine. This tour takes you to two breathtaking waterfalls in the morning, followed by wine tasting at two renowned wineries in the Hood River Wine Region and finishing with some free time to stroll through downtown Hood River. Gain insight into the region's geological history from your knowledgeable guide as you traverse scenic byways and enjoy views of majestic Mt. Hood and Mt. Jefferson. Whether you're a seasoned wine connoisseur or a casual enthusiast, this tour promises a day of exploration and discovery. - Visit beautiful waterfalls and two wineries in one day - Enjoy personalized attention on this semi-private tour - Pickup and drop-off service from the Portland Metro area - Tour duration typically runs from 9:00 AM to 5:30 PM

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.

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 an opportunity to do food pairings at a vineyard or seperate lunch stop. 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.

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.

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!

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.

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!

Drive the Willamette Valley yourself, with a GPS audio guide that plays automatically as you go. Your booking unlocks the whole region in the free Wine Trails app: pick your date and starting point — McMinnville, Dundee or Salem — choose the cellar doors you want from the 170 mapped across the valley, and the app builds your personal route with turn-by-turn narration. 193 stories cover Oregon Pinot country's people and places: as you climb into the Dundee Hills you'll hear how a 1980 tasting on French soil put David Lett's Oregon Pinot Noir two tenths of a point behind Drouhin's own Burgundy — and why Robert Drouhin bought sixty acres on these same hills eight years later. No group, no schedule, no guide — pause for a long lunch on McMinnville's Third Street, replay anything, and the audio keeps working when the signal drops on the back roads. You'll need a car and a designated driver; tastings are booked and paid directly with the wineries.

Our service offers six hours of entertainment with door-to-door service, and the ability to cover up to 90 miles of travel. Enjoy games, trivia, karaoke, fun lights, and the option to wear inflatable costumes. We provide pick-ups from homes and hotels in Knappa, Astoria, Gearhart, Warrenton, or Seaside. The best part is you won’t have to worry about driving under the influence, as we'll drop you back at your home or hotel.

The Columbia Gorge NSA features waterfalls, mountains, monoliths, terraces, resort towns, vineyards, orchards, and The River, harboring a plethora of fish and birds, and unique plants and invertebrates. In the early 1900s, Portlanders would drive their Model T cars along the Columbia River Highway to gaze at waterfalls. There is said to be over 4000 waterfalls; many are hidden away, but many are just a short hike off the Historic Highway. On this afternoon half-day tour you'll make new friends while exploring "waterfall alley", including views of the Vista House and a stop at Multnomah Falls, the tallest waterfall in Oregon and most visited site in the Pacific Northwest. Your expert guide will teach you about the natural history, cultural history, and wine background of the area, as you drive the Historic Columbia River Highway Scenic Byway. You'll continue on to stop at a vineyard in the Columbia Gorge American Viticultural Area (AVA). Tasting fees included.

Overlapping the Columbia Gorge National Scenic Area, and straddling the Oregon & Washington border, are the Columbia Gorge and Columbia Valley American Viticultural Areas (AVA). The Columbia Gorge AVA is the lovechild of the Columbia Valley and Willamette Valley AVAs. The Columbia Valley AVA is the largest AVA in the Pacific Northwest, and known for big reds with a bright mouthfeel. Come see the natural beauty of the Columbia Basin and Columbia Gorge through wine tasting. Your guide will teach you about the natural history, cultural history, and wine background of the area. Lunch is included; wine is not.

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. During your full day wine tour experience there will be an opportunity to partake in food pairings at a vineyard or a separate lunch stopall with a guide/driver to help make your experience safe, fun, and informative.

Winery hop through the Willamette Valley, known for its Pinots, with this small-group tour. You will visit three different tasting rooms where you’ll get the chance to sample wine safely, without having to worry about driving. You’ll also stop for lunch along the way, included in the price of the tour.