Top Ten Road Trip Experiences: Portland to Big Sur

In the 757 miles between Portland and Big Sur lie dramatic coastline, gigantic trees, rugged cliffs, wineries and plenty of time for self-reflection. I was hosting a group of clients at Pebble Beach and chose to drive these magical miles instead of fly. Pacific Coast Highway is regarded as one of the most fascinating road trips in the world.  You can find countless tips and guidance while planning your road trip using a book or online resource such as Northern California by Lonely Planet. I did plenty of research and landed on the following itinerary:

Portland –> Rogue River Valley –> Guerneville –> Russian River Wine Country –> Pebble Beach –> Big Sur –> Monterey –> Mendocino –> Redwood National Forest –> Portland

In ten days, I took in so much beautiful scenery and had so many adventures that I can’t possibly cover it all – so for this post I will just highlight my top ten 100 Percent experiences.

Top Ten 100 Percent Experiences

1.)  Putting this peanut butter pie in my face.  Guerneville Bank Club serves up fresh homemade ice cream and both savory and sweet pies. In my humble pie opinion, this ranks as the second-best peanut butter pie in the entire world. Enough said.  (Ranking first can be found at Screen Door in Portland, OR)

2.)  Sipping my way down Wine Road. Guerneville offers more than just peanut butter pie – it also delivers easy access to Sonoma wine country’s Russian River. The wine road consists of 50 miles showcasing 200 vineyards focused on perfecting pinots and zinfandels that will make your pretty little taste buds explode. I focused on Russian River Valley, a section that includes 130 wineries growing 30 different types of grapes. I planned my route over brunch and set out to cover Westside Road to West Dry Creek Road. The fall colors in the vineyard made it difficult not to stop every 20 yards to take photographs. My favorite winery was Porter Creek Vineyards due to its logo resembling a heart, exceptional service and even more exceptional chardonnay.

3.)  Floating off my wine coma on the Russian river. Fast forward about seven hours after my wine wanderings, and I found myself floating on an old inner tube at an old schoolhouse nature reserve. Recovering from a day of wine tasting never felt so good. And bonus critter sighting; as I was floating along I noticed a beaver fewer than ten yards away working much harder than I was.

4.)  Watching the evening happy hour ritual bagpiper at the Inn at Spanish Bay. Every evening as the last golfer walks off the course, a bagpiper serenades a lively happy hour crew at the fire pits and patio overlooking the sunset. When it’s foggy, grab a hot drink such as the Nutty Scotsman to warm your hands, throat and stomach.

5.)  Teeing off on #7 at Pebble Beach Golf Course. Although only 106 yards, I soon learned this hole is one of the most iconic in golf. Waves crash on the cliff that supports the green. I am not a golfer, but it seemed appropriate to take a swing in all its glory. The course also came with bonus critter sightings: Throughout the course you can find deer waiting eagerly for you to feed them Spanish moss from the trees.

6.)  Taking a picture of the most photographed tree in North America, the Lone Cypress. Since we were staying at The Inn at Spanish Bay, we had free access to the gated 17-mile drive which took us through scenic coastline views to the Lone Cypress, a native 250-year-old Monterey cypress and the inspiration for the famous Pebble Beach logo.

7.)  Finally seeing McWay Falls. McWay Falls in Big Sur has been on the top of my list for a couple years and rightfully so. Although only 80 feet tall, the dramatic landscape surrounding the waterfall beckons photographers from across the world. And, it came with yet another bonus critter sighting: On the drive there, I abruptly pulled over when I saw a flock of large California condors resting on a rock.

8.)  Appreciating the sunset from the headland trail of Russian Gulch State Park. Sometimes you have moments in life that remind you that every step that got you to this moment was perfect and in exactly the right time even when you felt out of rhythm. I don’t know who planted these daisies on the side of the trail or what they represented when they were planted. I don’t know how they survived in this cold and windy climate, or if the person who planted them knew how beautiful they would appear at sunset. I only know what they meant to me and how grateful I was to stumble upon them at exactly the right time in the perfect step.

9.)  Eating a beautifully prepared vegan meal at Ravens in Mendocino. Ravens is a celebrated vegetarian restaurant at the Stanford Inn by the Sea – featured in Oprah magazine, Sunset magazine, the San Francisco Chronicle and now I would recommend the tamales, but you really can’t go wrong with anything on this consciously prepared menu.

10.) Standing next to majesty in the Redwood National Forest. These trees have a special power to rejuvenate every cell in your body and mind. After spending a significant amount of time by yourself in a car, a lot of feels can come up to be processed. They did for me at least. These trees were my saving grace before my final stretch back to Portland.


  1. Jessica Lockley
    November 3, 2016 / 10:39 am

    Wow–absolutely amazing Bre. You inspire me!!❤️

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