Portland 5-Day Adventure: Waterfalls, Wine, and Haunted History Itinerary

Grab a quick breakfast at Stumptown Coffee Roasters to fuel up for the day. Then, embark on a morning journey to witness the majestic Multnomah Falls and other stunning waterfalls in the Columbia River Gorge on a half-day tour .

After the tour, enjoy a wine-tasting experience at the beautiful vineyards of the Willamette Valley. Sip on the finest local wines and indulge in a gourmet lunch at one of the wineries.

Return to Portland and have a sophisticated dinner at Departure Restaurant + Lounge, offering modern Asian cuisine with panoramic city views. Afterward, take a leisurely stroll in the vibrant Pearl District, known for its art galleries and upscale shops.

Begin your day with a breakfast of champions at Blue Star Donuts, where the brioche donuts are a must-try. Then, lose yourself in the endless aisles of Powell’s City of Books, the world's largest independent bookstore.

For lunch, head to Little Bird Bistro and enjoy their French-inspired dishes. Post-lunch, take a guided tour of the Oregon Museum of Science and Industry (OMSI), a fascinating place for science lovers of all ages.

Dine at Clyde Common, known for its European-style farmhouse fare, before enjoying an evening of laughter at the iconic Helium Comedy Club, where both up-and-coming and established comedians take the stage.

Enjoy a hearty breakfast at Tasty n Alder, famous for its innovative dishes. Then, set off on a full-day Mt. Hood Wine and Waterfalls Tour, combining the grandeur of Mt. Hood with the allure of local wines and waterfalls.

Savor a picnic lunch amidst the natural beauty of the region, provided as part of the tour. After returning to the city, take a relaxed walk in the Lan Su Chinese Garden, an oasis of tranquility in the heart of Portland.

Indulge in a sumptuous dinner at Le Pigeon, a renowned restaurant offering a creative and intimate dining experience. Conclude your evening with a visit to the PDX Night Market, where you can explore a vibrant mix of food, drinks, and local crafts.

Begin with a breakfast at Sweedeedee, known for its comforting, home-cooked meals. Then, set out on a full-day Oregon Coast Adventure Day Tour, exploring the stunning coastline, with highlights including Cannon Beach and Haystack Rock .

Enjoy a delightful lunch at Grassa, serving up some of the best handmade pasta in the city. Afterward, take a leisurely walk along the Pioneer Courthouse Square, often referred to as Portland's living room.

Conclude your Portland visit with a memorable dinner at Andina Restaurant, where you can savor the vibrant flavors of Peruvian cuisine. As a final treat, cap off your trip with a visit to Pittock Mansion to enjoy panoramic views of the city at sunset.