San Francisco to Oregon Road Trip Tritinerary

The only thing between you and an unforgettable culinary trip is a scenic Northern Californian road trip or a short flight away. The destination? Portland, Oregon. It’s a foolish game to try and summarize the culinary scene there, except to say it’s one hundred percent a city enthralled with food.

Seafood is definitely on the menu thanks to the quality fresh supply from Oregon’s Pacific coast, especially oysters which thrive in the cool, clean water. To sample some, Interurban pairs them with excellent cocktails, while Jacqueline has oyster happy hour, 5-6pm from Monday to Saturday.

Portland is proudly a high-low city, where food carts are as revered as the best restaurants. Arranged in ‘pods’ across town, Prost is home to Matt’s BBQ, where lines form for ribs, pork belly burnt ends and brisket. Away from the carts, Earl Ninsom is a chef generating buzz with his six restaurants, each with a spin on his native Thai cuisine. From the casual Hat Yai, through to Eem, a Thai-BBQ mash up with top-notch cocktails.

Some other eats worthy of a flavor trip: Burmese-style fried chicken and noodles at Rangoon Bistro, the award-winning Ken’s Artisan Pizza, Pasture PDX’s farm-to-table sandwiches or perhaps vegan tacos from Mis Tacones are your thing. Portland has a drinks pedigree to rival its food rep. Coffee culture is strong and it’s also known as a “craft beer capital.” Breakside and Great Notion are two breweries that come highly recommended, while Teardrop Lounge is a go-to for cocktails

One of the world’s premier wine regions, scenic Sonoma County is tantalizingly close to San Francisco, making it ideal for an upscale road trip. A first stop to consider is Osmosis, a day spa set in lush Japanese gardens. Their signature is the restorative cedar enzyme bath, a unique treatment said to relieve stress and ease aches.

35-minutes further by car is Healdsburg, a picture-perfect town considered the heart of Sonoma County. Part of its appeal is proximity to three renowned wine-growing regions: Alexander Valley (top Cabernet Sauvignon), the Dry Creek Valley (famous for Zinfandel) and the Russian River Valley (outstanding Pinot Noir and Chardonnay). Cellar door tastings are available at wineries in all three areas.

If you want to dine at Single Thread, Healdsburg’s acclaimed three Michelin-starred restaurant, you’ll need to be organized: tables are released on the 1st for the month ahead. Cyrus in nearby Geyserville offers a similarly refined experience, its ‘Dining Journey’ is available to just 12 guests per sitting.

90 minutes’ drive from Healdsburg, Sea Ranch is a coastal community developed in the 1960s by architects and designers with a vision to build in tune with nature. Sea Ranch Lodge is one of the original buildings and epitomizes the area’s prototypical style: earthy and timber clad. Renovated in 2021, the lodge has 17 rooms and nine rental homes and is a masterclass in understated luxury.

The Golden Gate may no longer be the longest or tallest suspension bridge, but it remains one of the most iconic and beautiful structures you’ll find anywhere. The best way to get up close is to walk across. There’s pedestrian access from sunrise to sunset and it takes about 30 minutes one way. Bikes are also allowed and can be rented from the Marina district.

Alternatively, the Golden Gate Welcome Center is a sensible place to start your exploration. Other recommended vantage points include Fort Point (tucked under the southern end of the bridge, you’ll also get a view of Alcatraz from here) and Presidio Tunnel Tops (chill in the park and see the bridge end-to-end), while Battery Spencer is the top pick on the north side and offers an elevated perspective.

Plenty of bakeries vie for the title of the city’s best San Francisco sourdough, arguably the city’s most famous food item. Stage your own test by picking up a loaf from Josey Baker Bread, Tartine, Acme or Semifreddi’s. Two other legendary food stops in the city are La Taqueria for burritos (winner of a prestigious James Beard ‘America’s Classic’ award) and chocolate maker Ghirardelli, with three distinct venues at its namesake square.

Portland’s outstanding food and drinks may get top billing (and be the reason you visit from San Fran) but the city’s nature stops are just as impressive. Dozens of forest parks, like Milo McIver State Park and Eagle Fern Park, sit just outside the city, but if you don’t want to go too far, Forest Park is 5,200 acres of wilderness on the city’s northwest fringe: that’s six times the size of Central Park. Explore with a hike or learn about the animal and plant life by joining a tour with a knowledgeable local guide.

30 miles east of the city is Oregon’s tallest waterfall—and one of the Pacific Northwest’s most popular natural attractions—Multnomah Falls (the two-drop cascade will be familiar to fans of the film Twilight). Popular equals busy, so plan your trip and note that timed permits are required during summer. Continue another 30 minutes east of the falls and you’ll reach Hood River, a pretty town surrounded by mountains and forest. Soak up the landscape with a unique railbike experience where you pedal your way along a rail track to see orchards, vineyards, pine forests and waterfalls.

For a nature fix nearer to San Francisco, Muir Woods Monument is the closest redwood forest, about a 40-minute drive from Downtown. Famous for being the oldest and tallest trees in the world, these majestic conifers can grow as high as a 30-storey skyscraper and live for 2000 years.

Make a self-guided day trip by reserving a parking spot and choosing one of the amazing trail paths. Be sure to do both in advance as there’s no phone service in the park. Guided coach tours from the city are also readily available.

About four hours north of San Francisco, the Avenue of the Giants is a unique way to appreciate the species. A 32-mile route through a dense canopy of giant redwoods, it’s widely considered one of the most scenic drives in the world.

For a wind-in-your-hair escapade, a sailing trip on San Francisco’s famous bay is both thrilling and iconic. The catamaran tours offered by Adventure Cat are a steady and scenic ride under the Golden Gate Bridge and around Alcatraz Island—you may even spot dolphins and other wildlife. The catamarans have a protected cabin but the rear deck trampolines are the exhilarating option.

The more adrenaline-charged boating choice is a wet and windy ride on an actual America’s Cup yacht, the USA 76. The tours run by ACSailingSF enable you to get involved and steer the boat, hoist the sale or operate a winch.

For a city adventure on dry land, the Presidio is a national park in the heart of the city, with photo-worthy views of the Golden Gate Bridge. It’s here that you’ll find the newly opened Presidio Tunnel Tops, 14 acres of parkland, trails and play areas designed by the celebrated team behind New York’s High Line.

One hour out of the city and you’ll reach scenic Sonoma County and the chance for aerial adventures. For epic wine country views, book a sunrise trip with Sonoma Ballooning, or soar through redwood forests with a Sonoma Zipline Adventures experience.

A perennial inclusion on lists of the ‘best beaches’ and ‘world’s most beautiful places’, Oregon’s Cannon Beach is a road-trip-worthy destination from San Francisco, taking in Sonoma County and Redwoods National and State Parks along the way.

The extreme natural beauty of the Oregon coast translates to total tranquility for visitors. Soak up the serenity with a stroll along the beach’s sandy shores. Or head out to the iconic Haystack Rock at low tide when you’ll see mesmerizing marine creatures up close: green anemones, sea stars, crabs, limpets and coral are among the sea life.

A 10-minute drive north is Ecola State Park, a top spot for whale watching in winter and spring but also a wonderful year-round vantage point of Haystack Rock and the headlands. Keep your eyes peeled for deer, elk, and eagles in the park. While you’re in town, Sleepy Monk is a locals’ favorite for coffee and bagels, or for something more substantial, Bistro’s menu features local seafood and both European- and Asian-inspired dishes. Maintain your Zen with a stay at the Inn at Cannon Beach, a garden-set hotel where complimentary passes to Cannon Beach Yoga Arts are offered alongside a library of books and games.