Top Portland Holidays

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.

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.

Experience a unique spa treatment that combines Oregon wine, self-care, and relaxation at the only vinotherapy spa in the United States.

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.

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings at 2 -4 hand selected boutique and estate wineries. Our tours can be customized to fit your desires, whether you’re interested in gourmet food pairings, private luxury experiences, or special event packages. Enjoy our transparent pricing with no hidden fees and comfortable vehicle for a relaxing day in wine country. - Explore 3-5 boutique and estate wineries with expert guides - Tailored private luxury tours for couples and groups - Enjoy exclusive reserve tastings and artisan food pairings - Flexible half-day and full-day options available

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on TripAdvisor, Google and Yelp for Private Tours & Group Tours. My commentary will give guests insider knowledge and our winery visits will give guests memorable encounters with winery staff. I can specialize the tour to suit your taste. I prefer wineries with amazing wine and beautiful views but, it's your choice. You can choose your wineries and can also pick them . Also, there are lunch choices to be made.

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 Tours, 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

Chef Sarah brings a cozy, down-to-earth vibe to this pasta-making class in Portland, making it easy for anyone to dive in and have fun with no experience needed. You’ll learn real pasta techniques in a relaxed, hands-on setting as you mix and knead fresh egg-free dough using simple ingredients like flour, water and salt. While your dough rests, you’ll work as a group with a prepared batch to practice rolling and cutting pasta with a machine. Then, Chef Sarah will show you approachable hand-shaping techniques that prove fresh pasta does not require special equipment. As you shape your dough, she’ll demonstrate how to make a rich butter sage sauce with garlic, lemon and olive oil, then cook the fresh noodles you cut together. At the end of class, you’ll sample the pasta made during the session and take home a full batch of fresh pasta to cook within the next three days.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Skip the dry history tours and lean into Portland's more eccentric side on this pub tour in the Hawthorne and Division neighborhoods. Combine beer with art as you try local brews and visit the area's most famous murals. Learn about local legends, from Bigfoot sightings to exploding whales, that you wouldn't discover on your own.

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.

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.

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.

Explore Portland's vibrant nightlife on a two-hour guided bike tour, where laughter and good vibes flow alongside refreshing drinks. The Classic Crawl takes you through the city's coolest neighborhoods and stops at three local bars, showcasing everything from neon-lit dives to quirky favorites. Perfect for groups looking to celebrate special occasions or simply enjoy a fun night out, this tour features onboard music and group photos to capture the memories. Come ready to pedal and dress up for the occasion—costumes are encouraged. - A public tour means making new friends, allowing others to join you on your crawl. - Two-hour guided bike tour through Portland's neighborhoods. - Visit three unique bars and enjoy a lively atmosphere. - Group photos and music provided for a memorable experience. - Minimum group size of 6 and maximum of 15 riders.

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!

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.

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

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.

We offer premium, curated wine experiences that are perfect for travelers, wine lovers, and private groups. Explore beautiful vineyard landscapes while enjoying expertly guided tastings at 2 -4 hand selected boutique and estate wineries. Our tours can be customized to fit your desires, whether you’re interested in gourmet food pairings, private luxury experiences, or special event packages. Enjoy our transparent pricing with no hidden fees and comfortable vehicle for a relaxing day in wine country. - Explore 3-5 boutique and estate wineries with expert guides - Tailored private luxury tours for couples and groups - Enjoy exclusive reserve tastings and artisan food pairings - Flexible half-day and full-day options available

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.

Home to some incredible bed and breakfasts, Newberg Oregon is centered in the heart of Oregon Wine Country. While you don't have to stay with one of our B&B partners, clients rave about combining our unique hospitality with that of a Bed and Breakfast experience. We offer complimentary pick-up anywhere in Newberg so you can stay in town or meet us at a convenient pick-up location. This tour is designed for individuals, couples, and small groups desiring curated wine explorations. If your goal is to find hidden gems in the valley that offer exceptional wines, incredible experiences, and that provide value, this wine tour is designed for you. These are wines you will be eager to take home, fill a wine cabinet or cellar, and those you are excited to share with friends and family. Each itinerary will feature an immersive experience to offer you a full day of unique and exceptional destinations. Grab a seat in one of our spacious and custom vehicles.

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.

Sample three of The Rose City's craft breweries, and learn Portland architecture and history, as you walk through the Pearl, Old Town, and West End districts. Taste the entire range of beer types, in the city that consistently ranks in the top three for number of breweries.