5 Day Itinerary: San Francisco to Portland Road Trip

How often have you heard someone wax lyrical about their fantastic road trip up the Californian coast? It seems that everyone has undertaken this drive, hitting the well worn paths from L.A. to Santa Barbara, Santa Cruz and San Francisco. But there is so much to explore on the West coast. A whole other state just north of Cali, waiting to be explored. Allow us to beguile you with the pacific coastal drive from San Francisco to Portland! A 5 day road trip through California and Oregon that will cement itself in your heart forever.

Witness the expanses of redwood forest, pines and lakes. Survey the ever changing coast, and stop by quaint but kooky towns. Drive, hike, bike and indulge your way up the coast, savouring the differences of these neighbouring states. You are going to fall in love with these lesser travelled paths, we promise!

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The San Francisco to Portland Road Trip: 5 Days of Glory

Photo by averie woodard on Unsplash

California and Oregon are two states which share a border, and a coast, but which change dramatically as you head further north. Closer to Canada’s Vancouver than it is to San Francisco, Portland has a history steeped in turmoil and triumph. It is the burgeoning hipster scene that has really gained traction for the city. But oh how it has flourished under that spotlight!

Craft Breweries in the Pearl District, gig venues strewn about town, the leafy and sprawling university campus looking far more east coast than west. Massive bookshops, secret whiskey bars, music on the streets, Voodoo Donuts. Not forgetting the marvellous display of bridges representing different ages and feats of engineering. This is a hangover from the towns burgeoning industrial phase during the second world war. When the war ended and work dried up, mob rule set in. It is a stark contrast with the city today. Their unofficial motto of the city being “Keep Portland Weird”. We’re on board with that!

Of course, San Francisco needs no introduction. The wonderful frenetic setting with its microclimate, hilly streets and stunning views. The music venues, shopping, wonderful bars and multicultural foodie title. Alcatraz and Golden Gate Bridge. Plus, it is only a short drive from Wine country! San Francisco has a colourful history and a fantastic buzz about it. So if you are planning on taking a road trip between the two, be sure to give yourself a few days either side so that you can truly experience the glory of each.

san francisco to portland road trip
Photo by Braden Collum on Unsplash

Things to do around San Francisco

Travel north over the bridge and into Mill Valley, and enjoy a long hike from the town centre to Stinson Beach. It will take around 7 hours, and is full of shifting scenery. Expansive hillsides turn to lush forests, opening up into a wonderful beach and cute little holiday town with a couple of tiny restaurants. Leave your car in Mill Valley, then take a taxi back after an early dinner.

Go to a gig at the Great American Music Hall or Slim’s. These are legendary venues that have history in their walls. Soak up some live music that could be anything from Rock and Indie to Jazz Blues and Hip Hop. You can check out the listings on their websites to pre-plan your trip.

Perhaps you could also take in a museum or two. There are a wealth of them downtown, including the SF MOMA. If you are up for a little childish fun, however, check out the Musée Mécanique on Fisherman’s Wharf. It is full of old antique arcade games and mechanical fancies, and has that true end of the pier feel. Visit on a sunny day before grabbing some fresh seafood in one of the local shacks or restaurants. Then walk back into town to burn those calories. Perhaps via Filbert St, the steepest street in San Francisco!

san francisco to portland road trip
Russian Gulch State Park, Medocino, CA – Photo by Harika G on Unsplash

Day 1: San Francisco to Eureka

Today you begin your San Francisco to Portland road trip! When driving out of the city, it is best to choose a late departure (after 7pm or so), or a super early one! Though earlier is better than late as you have the whole day to explore. Plus, seeing the morning sun over Golden Gate Bridge is magnificent. Stop in the quaint hippy town of Mill Valley for breakfast, and load up on coffee before driving to delectable wine country.

No doubt you will have heard of Napa Valley, and the wonderful wineries there. It was the iconic backdrop for films such as Wine Country and Sideways. However, if you want to do something a little different, drive to Sonoma to see the other side of wine country! Santa Rosa is bursting with glorious wineries such as Paradise Ridge. Stunning views, gorgeous wines, and an oh so Insta-worthy giant LOVE sign sits in the grounds. Surrounded by ornate iron structures. It is well worth your time.

But, if you only have time to visit one winery, we can only recommend the Coppola Winery. It is a genuinely thrilling blend of majestic scenery, fabulous wines and delectable movie memorabilia from owner and Director Francis Ford Coppola. And the whole aesthetic fits with his directorial cannon, a gothic edge amidst so much natural and horticultural beauty.

Wine tastings are super interesting too, and your guide is sure to be super knowledgeable. Sip on the splendour as they regale you with tales of the Coppola family and the inspiration behind the wines they make. Designated drivers, please remember to spit! Memorabilia, from Dracula to The Godfather and Apocalypse now, is sure to beguile the avid film buff, and when you are done sampling and perusing, there are a couple more delights to sample. Have a refreshing dip in the pool before taking lunch on the stunningly appointed veranda. We recommend the cheese board.

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This is an invigorating stop to take before you embark on the rest of your scenic drive. If you feel the need for a break, 2 hours along the coast is Mendocino, with Fort Bragg a little further up. Stop to stretch your legs, and perhaps visit the Blair house. This is the house in which Angela Lansbury lived in Murder She Wrote. If you’re not into visiting film sites, however, this is still a fantastic place to visit. Full of rugged natural beauty that is unparalleled in California.

Photo by Jim Witkowski on Unsplash

As the road veers from the coast, you will pass the Shrine Drive-thru Tree, near Myers Flat. Here, on the outskirts of Humboldt Redwoods State Park, you can drive through a redwood tree! A feat not likely on your bucket list, but an interesting experience nonetheless!

Todays journey should account for around 6.5 hours drive time in total, so you will be glad to arrive in Eureka. Your home for the night! Choc-full of old victorian buildings, the whole place is kind of eerie looking. A must see is the Carson Mansion, said to be the grandest Victorian house in America, and one of the finest examples of American Queen Ann Architecture. Stay at the Carter House Inn, dine at their in-house restaurant 301, and spend an evening relaxing whilst marvelling at the coastal beauty of Humboldt bay.

san francisco to portland road trip
A view of Mount Shasta – Photo by Andrew Sterling on Unsplash

Day 2: Eureka to Mount Shasta

Next up on your San Francisco to Portland road trip, drive 4 hours inland to Mt Shasta, close to Klamath NP. Take some time to indulge in breakfast and a morning stroll along the beach before hitting the road. It’s an invigorating start to the day! this region is rich in Redwood forests like the Redwood National and State Parks, so you can always take highway 101 north for a short spell to see the majesty of these towering ancient trees.

To get to Mt Shasta from Eureka, hit highway 299 driving east via Redding. If you fancy a break, you can find fun at the Turtle Bay Exploration Park. A sprawling complex of botanical gardens, arboretum and museum with fantastic natural history sections. Walk the famous Sundial Bridge over the Sacramento river. Designed by Santiago Calatrava, the 700 feet glass and cable bridge is surrounded by scenic park with breathtaking mountain views.

Once you have seen the sights of Redding, its time to get back in the car and cross Shasta Lake on highway 273. Crossing over the bridge is a beautiful sight, make sure you have a camera ready! This route will also take you past Shasta Caverns. If you have time, embark on a catamaran cruise on the lake, and join the guided two hour tour of the caverns. It is a genuine wonder, and guides are super knowledgeable.

From here, it is a 1 hour drive to Mount Shasta, 3600 ft above sea level. This town sits 9 miles from the summit of the ice-topped volcano, from which it gets its name. Drawing crowds of adventurers and spiritualists, the city is rich in outdoor pursuits and natural beauty. A stay here would make even the most hardened city-dweller rethink their ways. Year round, there are a tonne of activities to do and national parks to visit! And, while there are a host of hotels to stay in, you can also book into one of the many campgrounds for the night.

crater lake national park san francisco to portland
Crater Lake National Park – Photo by Cristofer Jeschke on Unsplash

Day 3: Mount Shasta to Crater Lake National Park

We are nearing the end of our San Francisco to Portland road trip! And today’s car ride will be about 3 hours, so enjoy a leisurely pace. Or perhaps head over to Klamath National Park before travelling further north! Klamath Falls is equidistant from Shasta and Crater Lake, and a great place to stop along the way to stretch your legs. It’s a fantastic jumping off point for those who like to hike, fish, hunt, or golf. It is also a top spot for bald eagle spotting, with the highest number of nesting bald eagles in Oregon making their home in the Klamath basin. To get up close to some local wildlife, Badger Run Wildlife Rehab is the one to visit. The owners are as delightful as they are knowledgeable!

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Aim to arrive early at Crater Lake National Park, as this is bound to be the best part of your trip from San Francisco. It is a chance to be immersed in nature. Make your home away from home in an onsite lodge and campground, and book in advance via the Crater Lake Hospitality website. Be sure to pre-book a boat trip on the lake, including a tour of Wizard Island. The crystal clear lake can be seen from space, and is filled entirely with rainwater and melted snow. So taking a dip will be very cold, even at the height of summer. Hike the Cleetwood Cove Trail to get down to the lake. But bring your best sturdy shoes! The steep descent can be treacherous.

Best views are awarded for those who make it up to the top of the Garfield Peak Trail. While short, it is steep, so pack some water and snacks for the top and spend a while enjoying those glorious views. Rim Village inside the park has everything you need to enjoy your stay without having to leave the site. Including a village shop for picnic supplies, a cafe and a couple of gift shops. You also have a couple of restaurants on site, if you don’t feel like cooking.

Photo by Justin Luebke on Unsplash

Day 4: Crater Lake to Hood River

Rise early to savour one last hike before you hit the road! Trust us, sunrise walk will grant you some stunning photo opportunities. This is likely to be the most serene part of your San Francisco to Portland road trip. Then it is goodbye nature as you hit two awesome towns on your 4.5 hour journey. The first is Bend, a small town in central Oregon famous for its craft breweries. The most notable being Crux Fermentation Project. It holds a large storehouse full of delicious crafty ales, alongside a delightful outdoor space. Beers are to die for, and their incredible food menu from their in-house kitchen is no different. Plus, an array of food trucks to choose from means everyone will be satisfied. This is perfect summertime hangout! If you have time, you could even embark on the Bend Ale Trail, the largest beer trail in the west.

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But aside from the mouthwatering glut of breweries, you also have lots of family fun and outdoor entertainment. You can tour of the roundabout art route, discovering local artists, visit the Mountain Air Trampoline Park, or enjoy the waters by kayak or paddle board at Tumalo Creek Park. There are also a host of water falls in the area, and even the Paulina Lake Hot Springs close by!

Tumalo Fall – Photo by Shawn McEntyre on Unsplash

Once you have had your fill of adventure in Bend, continue on highway 97, then onto the 197 toward Hood River. This is home for the night. We recommend staying at the Hood River Hotel for its rich history and perfect placement in the centre of the town.

This is where the designated driver gets the chance to experience some distinctly tasty wineries, distilleries and micro-breweries. And everyone can experience some high octane waters ports. Known as the windsurfing capital of the world, this really is the thrill seekers haven!

Yes, this is a fabulous location to experience water sports, but also hiking, biking with the fantastic mountain trails on offer, even horseback riding at Double Mountain Horse Ranch. If relaxing is the objective, enjoy retail therapy at the historic downtown shopping district. But the onus here is really on the real foodies experience. In the Mt. Hood and Columbia River Gorge area, man farms open to the public. The Hood River Fruit Loop is a majestic 35 mile route that will take you allover this land. Feel welcome to stop and sample the delights each farm and orchard has to offer. And when you are ready for dinner, you will find a wealth of farm to table restaurants in the area too.

This place is so great, in fact, you may want to schedule in an extra day to sample the extensive delights!

Photo by Isaac Ordaz on Unsplash

Day 5: Hood River to Portland

At last the time has come to meet your destiny in Portland. The ride will be over in 1 hour, so bide your time bidding adieu to the spoils of Hood. Enjoy a last action packed adventure on the trails or lake before you get back in the car.

If you have the time, (or aren’t ready to finish your San Francisco to Portland road trip), veer off track, pass Portland and visit Cannon Beach, a small city on the Oregon coast. Situated on the northwest corner, this location is famous for Haystack Rock. A 235ft sea stack resembling a large sharks fin protruding from the water, flanked by two large needles. The rock is often accessible at low tide, and has a cave system inside it! It is also protected by Oregon Islands National Wildlife Refuge due to the prominence of toucans nesting on the rock. If you are lucky enough to be there in June, there is a sand castle competition on the beach! For stunning coastal sights, reach Clark’s Point Of View using a hiking trail on Indian beach at the mouth of the Ecola State Park.

When it is time, turn the car around for the 1.5 hour journey into Portland. Your final resting spot! There are so many wonderful hotels in Portland, it can be tricky to no which one is best. To find your perfect hotel, use our handy guide of the quirkiest spots to rest your head.

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Photo by Zach Savinar on Unsplash

Welcome to Portland!

Thus concludes your San Francisco to Portland road trip. And what a city to end in! Portland is an explosion of food, craft alcohols, and culture. Visit the Japanese Gardens, or the Lan Su Chinese Gardens, get lost in the Portland Art Museum, or embark on the wonderful Underground Donut Tour. In fact, tours are ten a penny here. Everything from biking and ghost tours, to Willamette Valley wines! But if you have had your fill of tours, perhaps join a scenic cruise with lunch along the Columbia river.

There is just so much to fill your days in Portland! It is well worth doing some research before you arrive, lest you should miss out something that would make your trip even more special. But our advice is to definitely pencil in a morning of coffee and literature at the cavernous Powell’s Books store. Literally, this the worlds largest independent book store! Check their website to spy upcoming talks and events. Also, no trip to Portland would be complete without sampling the delights of the Multnomah Whiskey Library. Don’t be fooled by the bar downstairs. Head upstairs to see the endless display of whiskeys worth sampling, and sample the sumptuous menu worth salivating over. Take your time, this is worth savouring.

Now share this with your road trip buddies, and let the planning commence!

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James Ardimento has spent the last 12 years journeying around the globe ! With its precious experiences and tips he gained around Asia, South America, Europe and the US he is a precious asset for this blog and for its readers