Top Portland Seasonal & Special Occasions

Explore Oregon’s rocky northern coastline, dotted with beaches and sea cliffs, on a scenic full-day trip from Portland. Travel the picturesque US Highway 101 through quaint beach towns, stopping in Cannon Beach, Ecola State Park, and Oswald West State Park. Enjoy panoramic coastal views, geological wonders, and wind-swept beaches without the hassle of self-driving, and learn more from your guide than you would going alone.

**City Lights & Tiki Nights Cruise – Tiki, Tunes & Waterfront Views** Step aboard for Portland's most unique evening escape: the City Lights & Tiki Nights Cruise. This 21+ one-hour cruise along the Willamette River combines the fun of a floating lounge with views of the city skyline sparkling against the night sky. Sip your favorite drink as you glide past glowing bridges and the illuminated waterfront while music and social vibes set the mood. Every cruise is unique as the vibe tends to align with the energy of the group onboard, often ending in one big dance party. Whether you're planning a date, celebrating a special occasion, simply gathering with friends, or looking for a new way to enjoy Portland after dark, this cruise blends scenic views with lively island-style energy. **August:** 9:30 PM check-in, 10–11 PM cruise. **September & October:** Usually 8:00 PM check-in, 8:30–9:30 PM cruise. Please review all booking details and communications carefully before your cruise.

Escape the city for an afternoon exploring some of greater Portland's most scenic falls. Travel along the Columbia River Gorge, home to the largest concentration of waterfalls in the country, stopping at the epic Latourell Falls and Multnomah Falls. Enjoy panoramic views from the Crown Point Vista House and hear about the local legends and natural history of the area from your guide.

An unforgettable tour of the Columbia River Gorge's top 5 waterfalls and the Crown Point Vista House. With Waterfall Shuttle the views are better, the crowds are lower and you get an expert guide to show you around in a small group. Plus, we pick up from over 50 Downtown Portland hotels so you can access the wonder of the Columbia River Gorge without a rental car. Starting from your hotel in Downtown Portland, we start with a 45 minute drive out to the Waterfall Corridor. Working our way back one waterfall at a time we spend 2.5 of the 3.5 hours walking around and exploring each of the waterfall state parks. Plenty of time to take pictures, enjoy the natural beauty and make unique memories. Waterfall Shuttle is a tour designed to show visitors the best of our area. We strive to create unique and memorable experiences so that your time with us is some of the best of your whole vacation.

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.

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 the history and legends behind Portland’s Shanghai Tunnels on a small-group walking tour. Follow your guide beneath a restaurant to the tunnels, which once connected local businesses and hotels to the Willamette River. Learn about subterranean historic events and perhaps catch a glimpse of Nina, the resident ghost. Afterwards, resurface and enjoy three tastings and a full pint of locally produced beer.

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.

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.

Enjoy Portland from the water on this relaxed, island-style sunset cruise along the Willamette River. This 2-hour experience blends scenic views, tropical vibes, and a welcoming atmosphere for a memorable evening on the river. **August:** Check-in 6:30 PM, cruise 7–9 PM PT. **September & October:** Check-in 5:00 PM, cruise 5:30–7:30 PM PT. Cruise past floating homes, historic riverside properties, Waverly Country Club, and under 10 iconic bridges as the sky glows with sunset colors and the city reflects on the water. The route includes a unique stretch behind Ross Island for a quieter perspective rarely seen from shore. Enjoy open-air seating plus a covered palapa rooftop with wind screens for comfort in colder weather. Snacks and drinks, including cocktails, mocktails, beer, wine, and cider, are available for purchase. Whether sightseeing, celebrating, or simply unwinding, this sunset cruise is a fun, social way to experience Portland from a whole new view.

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.

Enjoy lunch along the Willamette River on a 2-hour cruise in Portland. Great for newcomers and locals alike, the leisurely cruise presents an expansive vista of Portland from the water. In addition to exceptional views and food, the afternoon tour also includes commentary from your captain and live entertainment. Prepared with local ingredients, your meal can be upgraded to include an appetizer and dessert.

This is Portland’s elevated sushi night out: a small-group, omakase-style progressive dinner across three top sushi spots downtown. Instead of tiny samples, you’ll sit down at each stop for chef-selected dishes—crafted to highlight different styles, cuts, and techniques—so you leave genuinely full and seriously impressed. Over 2–3 hours, you’ll enjoy a curated progression that can include nigiri, sashimi, specialty rolls, and seasonal plates (selection varies by night). Your guide keeps it fun and approachable while explaining what you’re eating, how to spot quality, and how to order with confidence the next time you’re at a sushi bar. All food is included, and group size is capped so the experience stays personal and high-touch. —and if you have dietary needs (gluten-free or vegan), message us after booking so we can plan your best possible menu. Why this is worth it: you’re getting a guided, chef-curated sushi progression at three restaurants in one night—without the guesswork.

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.

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.

Visit the gorgeous waterfalls of the Columbia Gorge without renting a car or sorting permits with this package, which includes round-trip transportation to the Waterfall Trolley from Portland and all-day access to the trolley shuttle. You'll have the freedom to visit different waterfalls and scenic areas with hop-on, hop-off access for added flexibility during this 8-hour experience.

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.

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.

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.

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

Experience the Willamette Valley, Oregon's largest wine region, on this wine-tasting tour from Portland. In a small group, head south of Portland to the Willamette Valley wine region, famed for its Pinot Noir. Spend the day tasting different wines (at your own expense) at three select wineries and learn about the region, and Oregon’s wine industry, from your guide.

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.

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.