5-Day Portland and Beyond Adventure Itinerary

Grab a quick bite at Flying Elephants at Fox Tower before embarking on a morning tour to the majestic Columbia River Gorge and its stunning waterfalls, including Multnomah Falls and Latourell Falls.

Enjoy a picnic lunch at one of the scenic spots in the Gorge. Afterward, indulge in a wine-tasting experience on the Mount Hood Wine and Waterfalls Full-Day Tour, where you'll savor local vintages amidst the natural beauty of the region.

Return to Portland and unwind with a sumptuous dinner at The Fireside, known for its wood-fired dishes and cozy ambiance.

Begin with a guided Delicious Donut Tour with Tastings, sampling some of Portland's most famous donuts. After satisfying your sweet tooth, take a morning stroll through the Downtown Coffee & Donut Tour to explore the city's coffee culture and historic landmarks.

For lunch, head to Radio Room in the vibrant Alberta Arts District. Post-lunch, immerse yourself in the city's history and haunts with the Portland Underground Shanghai Tunnel Tour with Beer Tasting or the Portland Ghosts, Poltergeists, and Psychopaths Walking Tour.

Dine at Expatriate, offering global-inspired small plates and a stylish, intimate setting. Cap off the night with a haunted pub crawl on the Portland Ghosts Boos and Booze Haunted Pub Crawl, visiting some of the city's spookiest bars.

Enjoy a hearty breakfast at Virginia Cafe before boarding the Portland 2-hour Lunch Cruise on the Willamette River. Take in the city skyline and enjoy a relaxing midday on the water.

Disembark and visit the Oregon Museum of Science and Industry (OMSI) for an interactive and educational experience. For lunch, try the eclectic menu at There Be Monsters in the Buckman neighborhood.

Conclude your day with a sophisticated dinner at The Solo Club, known for its global flavors and extensive wine list.

Begin with a visit to the iconic Mt. Hood, where you can choose to hike, ski, or simply admire the majestic peak. For breakfast, enjoy the ambiance and pastries at C-Bar PDX.

Return to the city for a leisurely lunch at Taylor Street Tavern, a local favorite. Spend the rest of the afternoon exploring the vibrant neighborhoods of Portland, perhaps visiting the Portland Art Museum or shopping at the Pioneer Place Mall.

Conclude your Portland journey with a memorable dinner at McMenamins Market Street Pub, where you can savor classic pub fare and raise a glass to the wonderful experiences you've had in the City of Roses.