Top Portland Holidays

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.

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.

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.

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.

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

Beneath Portland's vibrant streets lies a darker story. Join The Dark Below and explore the city's most chilling legends, notorious crimes, and haunted landmarks. Journey through historic Old Town and Chinatown as your guide uncovers tales of Shanghaiing, underground tunnels, tragic deaths, unsolved mysteries, and the restless spirits said to linger where Portland's darkest history unfolded. Visit iconic locations including the Shanghai Tunnel district, Old Town Pizza & Brewing, the Roseland Theater, Kells Irish Pub, and the waterfront where kidnapped sailors were once forced aboard ships bound for distant ports. Along the way, discover stories of vice, disappearances, and paranormal encounters that helped shape Portland's haunted reputation. Combining authentic local history, true crime, and ghost lore, The Dark Below offers an unforgettable journey into the shadows of one of the Pacific Northwest's most haunted cities. Guests must be at least 16 years old to participate.

Discover Portland's darker side on an adults-only haunted pub crawl through the city's historic Old Town district. Visit legendary bars, haunted landmarks, and infamous locations connected to Portland's most chilling ghost stories, true crime mysteries, and the notorious Shanghai Tunnels. Along the way, hear tales of restless spirits at Kells Irish Pub, the ghostly residents of the Benson Hotel, the unsolved murder connected to the Roseland Theater, and the tragic legend that still haunts Old Town Pizza & Brewing. Between stops, enjoy time at local pubs while exploring the history of sailors, bootleggers, performers, laborers, and outcasts who helped shape Portland's haunted reputation. Perfect for paranormal enthusiasts, history buffs, and anyone looking for a unique night out, this 21+ experience combines haunted history, local legends, and Portland's vibrant bar scene for an unforgettable evening after dark. All guests must be age 21+ and have a valid I.D. with them.

This experience combines the antioxidant-rich benefits of vinotherapy with a results-driven Caudalie Vinosource Hydra Facial. Guests begin with a wine-infused soak to relax the body and prep the skin, followed by a targeted facial designed to deeply hydrate, soothe, and restore radiance—delivering both indulgent relaxation and visible, glowing results. As the only wine spa in the USA, this is a truly one-of-a-kind experience you won’t find anywhere else.

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

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.

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.

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.

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.

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.

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.

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.

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.

Whether it's the stories of human trafficking described as the Shanghai Tunnels, the origin of the vampire tales in Twilight, or the crafty madam with the floating brothel, from fiery deaths to watery graves, we explore it all. The city of Portland Oregon was built on an ancient crossroads; known as a place to step into alternate worlds. What visit to the city would be complete without lifting the veil, for at least a minute, between the living and the spirit worlds? Weaving in historical tales with what fiction authors and filmmakers (including Twilight author Stephenie Meyer) with local ties have written about this place, we tell the stories of darkness, death and the liminal space that comes beyond. Our 1.5 mile (2.5 km) walking tour along the waterfront will include luminous views of the city lights along the river, encounters with our local corporeal spirits (the crows!), and plenty of recommendations to extend your gothic experience to restaurants, cafes and bars nearby.

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 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

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.

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.

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.