Credit Card Touring: San Francisco to San Luis Obispo

These past few weeks have been incredible. I just returned home from Europe after spending a week in France cycling the Alps and catching a stage of the Tour de France followed by some time spent in Barcelona. What I am about to recall is not the freshest thing in my mind, but it was such an awesome experience it has to be written about.

The weekend prior to embarking on my European adventure, my neighbor Michael and I rode our bicycles from our front doors near Golden Gate Park down to San Luis Obispo over the course of three days. A year prior, he and his wife got married and instead of having a bachelor party he wanted to go on a “mancation.” We had discussed different routes and San Francisco to San Luis Obispo seemed the best fit for our calendars.

The route planning involved looking over a California road map and calculating different distances to resting points in Google Maps. We ran different scenarios and ultimately chose to ride along Highway 1 for a majority of the trip since we didn’t want to miss the stretch of the 1 that runs through Big Sur. We kind of just winged it in terms of navigation, but in retrospect I probably would have liked to have a map from Adventure Cycling since we ran into some hiccups along our course.


Since we had a fair amount of distance to cover each day, we wanted to keep gear to a minimum, and we chose to stay at motels which also eliminated the need for camping gear. I was able to fit all of the gear in my handlebar and saddle bag. Michael was able to get everything into a backpack. This is roughly what I brought for three days of riding and one day of travel on AmTrak.

2 Jerseys
3 Bibs
3 Pairs of Cycling Socks
1 Cycling Wind Jacket
1 Wool Base Layer
1 Pair of Arm Warmers
2 Cycling Caps
1 Pair of Mountain Bike Shoes
3 Water Bottles (I have a third water bottle cage.)
1 Frame Pump
1 Set of Allen Wrenches
2 Tubes
1 Patch Kit
3 Pairs of Underwear (I probably could have done with less since I really only slept in them.)
2 T-shirts
1 Pair of Shorts
1 Pair of Flip Flops
Toothbrush, Floss, and Paste
Endurolyte Pills, Gels, and Bars

With all of my gear and filled bottles, my bike ended up weighing in around 38 pounds.

Day 1: San Francisco to Monterey – 125 Miles
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This was our “big” day for the trip. We had decided we were going to make a push to Monterey instead of staying the night in Santa Cruz since every inexpensive option to stay the second night in Big Sur was booked. Staying in Big Sur would have allowed us to create three days of similar distance, but since that was not an option, we had to front load the mileage.

Day one was full of mechanical issues, which seems to be expected when you are aiming to have a bit of an adventure. About a half a mile from home, Michael had to turn around to address a loose cleat and wobbly tire while I chose to add another bottle cage to my bike to bring a third water bottle. Around Half Moon Bay, Michael ran over a staple which was complicate by a valve on the replacement tube snapping in half. I ran over a drill bit near Pescadero that came out through the sidewall of my tire and that too was followed by a second flat just down the road.

The ride from San Francisco to Santa Cruz I have done a few times at this point. The only variation this time was to take Devil’s Slide just south of Pacifica. We decided on taking this path to minimize the amount of climbing, however, the tradeoff is a narrow windy road with very little shoulder and cars that travel near highway speeds. About 10 miles north of Santa Cruz, we passed by Swanton Berry Farm. I have yet to pass Swanton Berry Farm without stopping. Their strawberry shortcake is delicious and their self-service cash register is a reminder that honest people still exist.

The road past Santa Cruz was a bit tricky. We knew that keeping parallel to Highway 1, which was no longer suitable to ride on, would keep us moving in the direction toward Monterey. Meandering through neighborhoods and beach parking lots, we ran into a couple of dead end streets. Eventually we emerged onto a bike lane that ran through the farmlands of Watsonville and further south to the northern edge of Marina where we were forced onto the highway for a short stretch. At this point, the winds had shifted to a headwind and my tired legs and hungry stomach made me long to be done for the day. After not wanting to be on the highway any longer and exiting on a Marina off ramp, we were pleased to find a series of bike paths taking us through Marina, past the CSU Monterey campus, and into Monterey.

Day 2: Monterey to San Simeon – 110 Miles
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We awoke with sore legs and our bare chested Scandinavian neighbor barking some orders to somebody off in the distance. A few issues to tackle first thing in the morning then we were off.

We continued along the series of bike paths in Monterey down to Cannery Row then through Pacific Grove where we would grab breakfast. If there was a theme to our trip, it easily could have been amazing breakfasts. We were not shy when we ordered breakfast sandwiches, sides of pancakes, and extra syrup.

Growing up in Monterey, Pacific Grove, and Carmel Valley when I was in elementary school, this segment of the ride brought me back to my childhood. From Pacific Grove, we turned onto 17 Mile Drive which took us into Pebble Beach and past some of the most famous golf courses in the world. Looking at the golfers and their caddies, we smiled knowing their experiences were great, but that ours would be grand. Passing by an older English gentleman towards the edge of Pebble Beach, we struck up a conversation which led to him leading us through Carmel and to the mouth of Highway 1, which would lead us along some of the most beautiful coastline in America.

The conditions were absolutely beautiful that day. It was a surreal mix of sun and fog which made the dramatic coastline even more so. We rolled into Big Sur just past noon where we would sit down at The Maiden Publick House for a proper English meal. I could have easily sat there all day, sipped on microbrews, and enjoyed the shade of the redwoods, but we still had nearly 80 miles of rolling coastline to reach our next destination, San Simeon.

We got back on our bikes, slightly drunk from all of the calories, and pushed on. I wanted to stop every five minutes or so to snap a photo, but I knew if I did we wouldn’t make our destination before nightfall. We passed through towns every 25 miles just as our new English friend, Bill, had told us we would. We rode into the mist head on and emerged above a sea of fog just to descend right back into it at the next bend. It was dizzying at times to look over the roadside barriers that were knee high to see a sheer cliff that dropped straight into the ocean 600 feet below.

What an amazing day!

Bill warned us of a climb that had five false peaks and after every climb that felt beyond moderate, Michael and I would assure each other that the last one was it. We began what we thought would be our final descent. Descending to only feet above sea level, we arrived at the base of the climb. Bill wasn’t kidding. There were exactly five times when I said, “Fuck. That wasn’t the top?”

The sun began setting behind the ocean cliffs at our backs as we made our way slightly inland to the final stretch of the day. With a stiff tailwind and a mysterious fog straight out of Treasure Island, we formed a paceline and ripped through the final 20 or so miles of the day. The sun had set as we emerged back on the coast with rolling hillsides to our left. The moon lit up the night and off in the distance we could see the lights of Hearst Castle and San Simeon.

Day 3: San Simeon to San Luis Obispo – 45 Miles
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With all of the mileage in the bank, day 3 was all about relaxation. We stopped in Cambria for another big breakfast where I discovered that country potatoes taste better with maple syrup than they do with ketchup. We rolled along Highway 1 in the direction of Los Osos where we planned to make a left turn at some point to go to San Luis Obispo. With time at our disposal, we took every opportunity to roll down gravel roads, dirt paths, beach walkways, and swamp crossings.

Taking the final left at Los Osos, Michael thought it would be a good time to drop the hammer. We would be going “Cancellara” pace for the rest of the way. I tried to suck wheel for as long as possible, but with a 38 pound bicycle it was hard to maintain 27 miles per hour.

As we rolled through San Luis Obispo and took the final turn to our motel, we were greeted with cheers from a group of cyclists having beers at Central Coast Brewing. They poured us fresh pints and made the perfect ending to a perfect tour!

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