Celebrate Valentine's Day in Portland (Updated 2026)

Afternoon Portland City Tour
More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving...
$85

Jeff Davies has 30+ years of guiding the Multnomah Falls / Mt. Hood "Loop" Tour with Columbia River Gorge Waterfalls. I have top reviews on...
$1,334

Tasting the Gorge by Ebike
Try to wipe the smile from your face as you experience an electric bicycle while enjoying a sensory overload of smells, tastes and sights. This...
$150

Enjoy Portland from the water on this relaxed, island-style sunset cruise along the Willamette River. This 1.5 to 2-hour experience blends scenic views, tropical vibes,...
$55

Download GuideAlong’s self-guided driving audio tour of the best of Oregon’s Mount Hood Loop. Discover the dramatic Multnomah Falls, scenic roads through the Columbia River...
$20

Ever wonder what animals and plants you're seeing when you hike and what makes each one special? Wish you could have a naturalist along to...
$60

Full-day Columbia Gorge Hiking
The 85-mile (137-km) long Columbia Gorge NSA would be a national park if it weren't a critical transportation corridor. It features waterfalls, mountains, monoliths, terraces,...
$149

Join an intimate, Oregonian-led Private tour of the Columbia River Gorge and Mt Hood with Portland, Oregon's original tour and adventure company. Your seasoned, local...
$200

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by...
$175

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by...
$1,652

Discover the rugged beauty of the Mt Rainier National Park on this full-day trip. Travel aboard a comfortable van through historic Gold Rush towns to...
$350

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on City Helicopter Tours, Google and Yelp for Private Tours...
$1,292

Journey along Oregon’s breathtaking coastline stopping for viewing wildlife, pristine beaches and rocky cliff headlands. Learn about natural, Native American and regional history. Northern Oregon...
$1,334

The best wineries in Oregon lie just under an hour’s drive from Portland in the Willamette Valley, a thriving wine region known for its outstanding...
$138

City Lights and Bridge Tour
Classy pontoon boat tour by or through 10 bridges and around 4 islands! We depart in sight of the new Sellwood bridge, then cruise past the Iconic...
$99

Our Sips & Sights Tasting Cruises pair local wine tasting with a 2-hour sightseeing and social cruise on the Willamette River! Featured wineries: • Oct...
$70

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...
$35

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...
$35

Embark on an intimate, Oregonian-led private group tour of the Columbia River Gorge and waterfalls. Your seasoned, local guide will take you on a 4-hour...
$979

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...
$30

Experience Oregon’s crown jewel of state parks on this guided hiking tour of Silver Falls. Known as the ""crown jewel of the Oregon State Parks...
$179

