Ultimate 5-Day Portland Adventure Itinerary Itinerary

Kick off your morning with a guided Portland Guided Delicious Donut Tour with Tastings, visiting some of the city's best donut shops. Then, take a stroll through the Portland Pearl District, known for its art galleries, boutiques, and vibrant street art.

Enjoy a delectable lunch at Tasty n Alder, offering a menu of international flavors. Afterward, descend into Portland's history with the Portland Underground Shanghai Tunnel Tour with Beer Tasting, an intriguing journey through the city's hidden past.

Dine at Departure Restaurant + Lounge for a modern Asian dining experience with stunning views of the city. Cap off the night with handcrafted ice cream from Salt & Straw, known for its unique and inventive flavors.

Start with a hearty breakfast at Grassa, known for its fresh pasta and local ingredients. Then, take to the water on the Portland Willamette River 2.5-hour Dinner Cruise, enjoying the sights and a delicious meal onboard.

After disembarking, explore the city's food scene with an Portland All-Inclusive Walking Food Tour, sampling a variety of culinary delights from local eateries.

For a late-night snack, head to Clyde Common and indulge in their European-style tavern fare. Enjoy the rest of the evening at leisure, perhaps exploring Portland's vibrant bar scene.

Begin your day with breakfast at Pok Pok, known for its authentic Thai cuisine. Then, immerse yourself in science and industry at the Oregon Museum of Science and Industry (OMSI), exploring interactive exhibits and the USS Blueback submarine.

Grab a quick bite at Powell’s City of Books [13305], where you can enjoy a sandwich surrounded by the vast collection of literature. Spend the rest of your afternoon at the International Rose Test Garden, where you'll be surrounded by the beauty and fragrance of thousands of rose bushes.

Dine at Andina Restaurant, offering a menu of authentic Peruvian dishes in a vibrant setting. After dinner, take a leisurely walk through the Portland Japanese Garden, known for its tranquil beauty and traditional Japanese landscaping.

Enjoy breakfast at Ava Gene's, known for its rustic and seasonal Italian dishes. Then, set out on the Portland Mt. Hood Day Tour, where you'll witness the majestic beauty of Oregon's highest peak and the stunning surrounding landscape.

For lunch, indulge in the famous chicken and rice dish at Nong's Khao Man Gai. Afterward, take a leisurely drive to the serene Willamette Valley, known for its vineyards and world-class wines, and enjoy an afternoon of wine tasting.

Conclude your Portland adventure with a sophisticated dinner at Little Bird Bistro, offering a menu of French-inspired dishes. Reflect on your journey over a glass of wine, and perhaps take a stroll through the Portland Steel Bridge, admiring the city lights and the memories you've made.