Oregon Food, Brews & Views: A 7-Day Luxury Journey Through City, Coast & High Desert

Arrive in Portland and check into The Nines or the Heathman Hotel, both ideally located for exploring the city on foot. Portland’s culinary scene is one of its strongest highlights, with an emphasis on seasonal ingredients and creative approaches to dining. Spend the afternoon exploring nearby neighborhoods, visiting Powell’s Books (the largest independent new and used bookstore in the world, btw), or enjoying a relaxed coffee stop, I highly recommend Nossa Familia. End the evening with dinner at one of the city’s standout restaurants like Le Pigeon and a nightcap featuring local spirits or wine at 2NW5 or Multnomah Whiskey Library.

Spend the day exploring two of Portland’s most polished and walkable neighborhoods: the Pearl District and Northwest (Nob Hill). The Pearl is known for its converted warehouses, art galleries, boutique shopping, and excellent dining, making it ideal for a relaxed morning of exploring on foot.

From there, head into Northwest Portland, where tree-lined streets and historic homes create a charming backdrop for local shops, cafés, and wine bars.

These neighborhoods are perfect for travelers who enjoy great food, thoughtful shopping, and a refined yet approachable atmosphere. Plan to linger at lunch, browse independent local boutiques, and enjoy an unhurried afternoon before returning to your hotel or heading out for dinner nearby.

Travel south to Newberg and check into The Allison Inn & Spa. Today focuses on a thoughtfully curated introduction to Oregon wine, particularly the region’s celebrated Pinot Noir. I recommend visiting these wineries to allow time for scenic drives and relaxed tastings: Domaine Serene Winery, Ponzi Vineyards, and Bergstrom Wines. Return to the hotel for time at the spa. Choose from many luxurious treatments; my favorite is the Zen Den Garden Massage, a tranquil essential oil massage outside in a private serene garden. Then it’s time for farm-to-table dining at JORY, this on-site restaurant at The Allison. Don’t miss the scallops or the beef tartare, a must try!

Depart wine country and travel west toward the Oregon Coast, where forested roads open up to sweeping ocean views. Check into Headlands Coastal Lodge & Spa, located just steps from the beach in Pacific City. Spend the afternoon walking the shoreline, enjoying coastal scenery, stopping in at The Pelican Brewery to keep the trend of trying local brews going, or relaxing on your balcony with a view of Cape Kiwanda. Evening is best spent savoring fresh seafood while watching the sun set over the Pacific at the Meridian, an innovative Pacific Northwest dining experience.

Travel inland to Central Oregon, where the landscape transitions to high desert and mountain views surround you. Check into Brasada Ranch, a peaceful retreat with expansive scenery. One unique and fun activity available on site is horse back riding or you can try out what it's like to be a wrangler. Join the experienced wranglers and feed, groom, and saddle the horses. The afternoon is ideal for settling in, enjoying the views, or exploring the property at a relaxed pace. Dinner with a sunset backdrop is a highlight of staying in this area.

Enjoy a full day in Bend, known for its extensive brewery scene and easy access to the outdoors. Balance brewery visits with time to explore scenic viewpoints or enjoy a casual outdoor activity. During the warmer months, participate in one of Oregon’s favorite statewide summer pass times, river floating. In Bend, they make it easy, you can rent an inner tub, paddle board or kayak and float the river. In the height of summer, it’s basically like a big party on the Deschutes River. If you need more of an adrenaline rush, rent an ATV from Octane Adventures and explore the miles and miles of trails in the backcountry. Bend’s relaxed and sometimes exciting energy makes it easy to mix good food, good drinks, and fresh air. Return to Brasada Ranch for a quiet evening under wide-open skies and of course, dinner at one of the two dining options on site.

Spend your final morning enjoying the calm surroundings at Brasada Ranch. Whether it’s a leisurely breakfast, a short walk, or simply taking in the views one last time, this is an calm and serene way to end the journey. Depart with a deeper appreciation for Oregon’s diversity, from city food scenes to coastal beauty and high desert landscapes.