The Historic Way to Boat the Bay

It’s easy to see how at a glance passers through see a high/low binary between SF and the Town, but there’s so much more to see beyond the commuter water routes. And even better stories behind the sights.

· 5 min read
The Historic Way to Boat the Bay

East Bay Yesterday Boat Tour

September 19, 2025

The ferry has been my preferred mode of transit across The Bay for years. I hang out in the bike section and meditate on the views before getting on with business. Oakland’s industrialized estuary outbound, and San Francisco’s trazillion dollar skyline back. It’s easy to see how at a glance passers through see a high/low binary between the two. I chose The Town, so you can give me the finger all day, Salesforce Tower, but I rejected YOU first. Mmmkay?

But even a dyed in the wool Five-and-Dimer like me only gets the tiniest snapshot of the waterfront, the geologic feature that, in its round about way, drew us all here. There’s so much more to see beyond the commuter water routes. And even better stories behind the sights. 

And if you want stories, there’s few better go-tos than Liam O’Donoghue. Liam is a fellow multi-hyphenate hustler. Author, podcaster, journalist, docent, historian Liam O’Donoghue has led  Oakland history boat tours of the bay since 2018. I learned of the excursions from his award-winning East Bay history podcast, East Bay Yesterday, and have coveted an opportunity to set sail. That opportunity arose on Friday. 

Our boat, the Pacific Pearl, set out from Emeryville Marina around 5. The trip was BYOB, so I pocketed a microbrew. Others came better supplied. The crew gave us our safety briefing and we sailed out of the marina. O’Donoghue painted a picture.

 “Before colonization, when hundreds of Ohlone village sites ringed the bay, as they had for millenia. Each of those village sites was marked by a shellmound - the biggest one, in Emeryville where Temescal Creek entered the Bay, was over 60 feet tall.”

The “Classic Oakland Tour” stops included the Port of Oakland, Jack London Square and Alameda with Judge John Sutter Regional Shoreline the first highlight. He held a squeegee aloft. 

“This will come up later .

”The Bay Bridge arched westward while to the left was the last remnant of the old Bay Bridge, still imposing even reduced to a fraction of its former self. A few feet below us, we learned, was the trans-bay tube. Impressive when you think about all that people-moving. But that is just the now. This historical moment.

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“If there’s one major theme on this tour - it’s transformation. This tour isn’t just facts and random trivia – it’s about how and why the Bay Area has changed over the past few hundred years… how it’s continuing to change.”

Coupled with O’Donoghue’s narration, there’s the now, the old Bay Bridge’s mid-century origin story and the Bay’s pre-colonial history. Drifting into the port, one of the busiest in the nation, we were dwarfed by the container ships, and even more by the cranes. There was another of Oakland’s hidden gems, Middle Harbor Shoreline Park. The park, reclaimed from 38 acres of industrial ruin, was largely the work of activist Chappell R. Hayes. An observation tower was named in his honor, for this gift to the community. 

Union Point park caries a slightly less sentimental story. 

Sigame was Created by artist Scott Donohue. It combines the body parts of 20 different women - freakish!

It was originally at Ogawa Plaza but moved  because it looks like the woman is wearing a Hannibal Lecter-style flesh mask.”

This park’s tower is somewhat beautified landfill. There so much landfill that comprises the shoreline. So much obscured from view like jet fuel pipes, industrial grain silos (and grain-loving geese) and eccentric, floating homes. 

But the best reveals are historical. Our pass through Jack London Square brought to mind Oakland’s grafty, wild west origins. Horace Carpentier, Jack London, “King” Macmanus. Competing ferry systems that had a strong “Gangs of New York” vibe. 

And let's not forget the squeegee. “Invented in Oakland! Ettore Steccone was born in Northern Italy in 1896 and came to the US. How was he gonna get rich? As a window cleaner, of course! He invented the squeegee because he wasn’t happy with the existing window cleaning devices.”

We passed by and waved to a number of fellow water vessels. A floating, remote controlled, hot tub with two, disappointingly well-behaved passengers. FDR’s floating White House, the Potomac. Most notably, there were docked and floating Transbay ferries. The bay was linked by ferries for decades before they fell out of favor with the building of bridges and rise of trains and automobiles. There were none for thirty years until the Loma Prieta necessitated their return.

And while a great deal of the waterfront is still claimed by industry, virtually none of it was publicly accessible for much of the 20th century, and what little was often came with hazardous obstacles and pollution. This is all recent history, easily lost or obscured. Thankfully, here in the bay, the trend toward conservation and wetland renewal has continued, as has the expansion of the restored ferry system. 

I spotted a seal’s head bobbing just as we embarked on our journey. O’Donogugh pointed out osprey nests built atop posts in the shipping channel. The north west edge of Alameda Island, where the Navy Base once was, is a superfund; the land and groundwater so contaminated it’s unsafe for development, while the surrounds have seen a building boom. Nature rushed into that vacuum and is patiently doing its millenia-long work of undoing man’s harm. 

One of the bay’s protected bird species is the cormorant. We passed under a cormorant colony under the new Bay Bridge. Moving them from their digs on the old Bay Bridge was an undertaking, and cost more than $10 million. “It took the use of decoys, bird-call recordings and dried-out holiday wreaths — and a limitless amount of patience...There may be as many as 700 birds residing on the new east span.”

As if on cue, the birds released a fish-smelling shower of that night’s dinner. “Faster! Faster!” I don’t think there were any casualties. If there were, you couldn’t tell. Everyone I saw was having a blast. I’m bringing my son next time.