Leaving Our Hearts (and Feet) in San Francisco
- Amy Digges
- Jul 18, 2023
- 6 min read
We are back on the road and it feels so good to be traveling again. I’ll admit that I have the heart of a wanderer so staying put for too long makes me antsy. Seventeen years ago, Kip and I came to San Francisco to celebrate our one year anniversary.

Now, we had the perfect reason to return. My oldest (and I mean that in the nicest way) and dearest friend, Nicole, moved out here two years ago. We met at age 5 and she has been a constant in my life ever since. So, of course, we had to visit.

Masks are optional on flights now and yet, considering the fact that Every. Single. Time. I have been on a flight to the west coast, I contract some horrible illness en route, we were not taking any chances.
We arrived at our destination, a gorgeous place in the heart of the Pacific Heights neighborhood. The area is dotted with grand Victorian homes and wide streets that seem to continue upwards and upwards and…upwards. It makes you wonder what madman saw this topography and said, “Yes, let’s build a settlement here.“

The first morning, we decided that we should get some exercise, and instead of taking an Uber to catch the boat to Alcatraz, we should take a leisurely walk to Pier 33 and see the city in the process. San Francisco is a place that is totally walkable (if you’re a mountain goat) so climbing up the roller coaster hills on foot requires a certain forward leaning posture that may or may not help the cause but seems to provide the slightest extra oomph. Clearly, we aren’t the only ones who cursed the upward climb.

Through parks and gardens we traversed the city, gawking at the celebrity homes of Francis Ford Coppola, and the setting for Mrs. Doubtfire. It’s like an episode of “Lifestyles of the Rich and Famous” (you know you want to say that with an accent, right?). One such home happened to be Danielle Steele’s monstrosity that looks more akin to the Smithsonian.

Based on the map, it was really just a handful of blocks and the water is literally right ahead! Did I completely ignore the GPS’ estimated time of arrival and think, “We aren’t such slow walkers that it will really take us an hour and nine minutes to get there?” Yes, I did. That view of the water, like a mirage, never seemed to get closer.

What I didn’t realized is that a San Francisco block is quadruple the length of a Baltimore block. Onora was lagging behind (rightfully so) and finally asked, “How much longer?”I checked the GPS, now trusting it, and sheepishly responded, “28 more minutes.” When all was said and done, it, in fact, took us about the same time as the GPS suggested. Side note: I retroactively checked the distance we covered. A mere 3.2 miles. Liam says, “On vacation I get far more exercise than at school.”
Bedraggled, we arrived at Pier 33 and sat on the asphalt near the dock eating our packed lunch. Bellies full, we asked Onora how she was feeling after the long walk and she announced, “I feel like it’s a brand new day.” She recovers quickly!

We boarded the boat to Alcatraz under a bright sun. Wind-whipped yet delightful, the ferry to Alcatraz has stunning views of the choppy seas, two bridges shrouded in fog, and a beautiful backdrop of the city skyline.


Ahead of us looms the most famous prison in the country, The Rock. Figures such as Al Capone and Machine Gun Kelly resided here along with lesser known “criminals” like James Quillen who was sent to Alcatraz for stealing $16.38 from a convenience store? Something seems fishy about that. With cells just big enough for a toilet and a twin bed, some inmates on the top tier cell block had a view of the San Francisco Yacht Club. Adding insult to injury, on summer nights the music and laughter carried across the bay.
What always strikes me about Alcatraz is the families of the prison staff who lived on the island for all those years. It‘s an odd juxtaposition. In a way, it‘s an innocent and idyllic (albeit isolated) existence for all of those children and yet they reside in the literal shadow of a maximum security prison.
Gaelan and Onora filled out an informational scavenger hunt pamphlet about Alcatraz during the tour and were subsequently “sworn in” as Junior Rangers. They took their oath very seriously.
Back at Nicole‘s, we enjoyed a cozy evening being serenaded on the front lawn by Nicole’s son Graham, sipping wine, and catching up. Though, in all honesty, there’s not a whole lot of catching up to do considering Nicole and I talk almost daily.
Thursday morning brought the usual dose of fog that hangs directly over the city. We layered up and rented bikes for our day’s adventure. Gaelan and I were tandem buddies for the day and spent much of the time cursing our incompetent bike as it clicked, rattled, and shifted gears unexpectedly, leaving it difficult for Gael and I to find a good rhythm. My favorite feature was my seat that swiveled each time Gaelan accidentally turned his handlebars. He could shift me almost 90 degrees with a minor adjustment.

Getting up the hills to the bridge proved a bit more difficult for Kip and me as we had to both pull the dead weights behind us. God bless ‘em, for as much as they tried to put power in their push, those little legs could only do so much. I walked the bike more than I rode it.
Biking the bridge itself is like playing a video game with dangerous obstacles thrown in your path. It becomes a game of chicken with bikers coming from the opposite direction as you quickly assess how much time you have until you move right and narrowly miss a pedestrian. You have to keep your wits about you as people stop mid-stride to snap a picture, serious cyclists weave around you shouting ”On your left!” and tractor trailers blow by, simultaneously shaking the bridge and sending gusts of wind that threaten to topple you off the bike. I loved every second of it but by the time we were across the bridge Gaelan‘s arms hurt more than his legs from white-knuckling the handlebars.
The Bay area has its own little micro-climates so as soon as you cross the bridge into Marin County, the weather changes dramatically and shedding those layers becomes a necessity. The ride down into Sausalito is simply a coast. No pedaling required! In fact, if I didn’t have my hands depressing the brake on the way down, I felt that our crappy little bike would have simply rattled itself to bits and shed its parts on the way down.
Ah, Sausalito…where even the trash cans are well designed and the cross walks are beautiful.

It’s a place that corners the market on picturesque. The modern bungalows that perch on the hillsides seem to defy gravity and require engineering geniuses to keep them in place. And, wow, the views from that height must be something spectacular.

With each step, Liam could be seen crouching, his face peering at a succulent, practicing his photography skills. Guaranteed his camera roll will be 99% plant life at the end of this trip.
Pulled pork tacos, falafel, burgers, and a well-earned beer at the Joinery restaurant brought the outside in as succulents hung from above the simple wooden tables and the large doors propped open to take in the view of the bay marina.

Now, this is the way to do it! Rather than hoofing it back up to at steep hill from Sausalito and across the Golden Gate, you simply park your bike on the ferry and enjoy the view back to San Francisco. Onora had the absolute time of her life and Kip joked that, if her state of joy on a boat is any indicator, she will be getting her captains license in the future.

This was the first time we had an opportunity to see the entire bridge without a part of it covered in a blanket of fog.
A wonderful night at the Tailor’s Son restaurant, just the adults, for an assortment of creative Italian dishes, was just what we needed.

My excitement at having Nicole with us all day on Friday, her day off, was off the charts. She drove us to Mill Valley to visit her old stomping grounds. Where Sausalito is ritzy and upscale, Mill Valley is upscale in a more mellowed out and approachable way. It’s like Barbara Streisand versus Keanu Reeves.
We hiked the beautiful Cascade Trail, let Quinn “zen out” a bit, and continued our way up the road by car for a delicious lunch and to see the magical, all encompassing, Pacific Coastline at Muir Beach Overlook.

Our time in San Francisco was almost up…but not quite…After we cross the interior of California, watching the mercury climb as we head four hours west to Yosemite, we will return for one more night with Nicole and family. After all of our walking, at least our feet are prepped and limbered up for the hiking we plan to do in Yosemite! Thank you, my dear friend!! Love you.
I would never say that this one was not up to your standards! I think it is wonderful and informative and shows lots of love between family members and you and Nicole as well! Great job Ame!
I love your adventures! You are some brave souls for riding across that bridge! Also, I swear Nicole does not age. You two look just the same—beautiful as ever! 💜