A Whirlwind Tour of Jack London Square Eateries

A Whirlwind Tour of Jack London Square Eateries

And a Marina Review from Two New Sailors! 

We sailed into Jack London Square on a brightly lit fog-free morning, gently gliding under the Bay Bridge, one of the longest bridge spans in the United States. It consists of two sections; the western section, the double-decker part, and the eastern section which was reconstructed as a single layer after the 1989 Loma Prieta Earthquake.

Piece by piece, we shed our foulies–that foul weather gear we had lived in for the past few months; heavy raincoats, rain boots, stocking hats, layers of socks, and flannel shirts fell to the deck. Years ago, I had come to Oakland regularly, as an artist in the Jack of All Trades Craft Fair. Oakland has grown, has changed, and has city problems; but, she also has a piece of my heart and I was looking forward to seeing if the growth and change had warped her, and if so how badly.

The Tillicum’s crew welcomed us; our acquaintance from the sea near Neah Bay, when their transmission interrupted the quiet journey’s radio waves.

“Gypsea Explorer, Gypsea Explorer Gypsea Explorer–this is Tillicum. Can you go to channel 68 Alpha?” When we did, the next six words would build future friendships.

“Do you have wind over there?”

Tillicum met us at the dock and grabbed our lines. After exchanging greetings, we were ready for our first stop; Heinold’s First and Last Chance Saloon. I hoped it was still there.

Within moments, we stepped through the wooden door and found ourselves under 19th-century gas lamps and a world away from the one we had just left.

Heinold’s “First and Last Chance” Saloon

Built from the timbers of an old whaling ship, the room has a wooden bar and three tables. A single wrong step could send you tumbling down the steeply angled ground, sloped by the 1906 quake, reminiscent of a wayward marble in a kid’s game.

Today, vintage signs adorn the walls, and hundreds of business cards hang overhead along with signed hats and helmets from generations of the working elite; firefighters, police officers, construction workers, and sailors. The building was originally home to local oyster harvesters, but in 1833, it transformed into the much more profitable business venture of the saloon. 

In the late 1800s, seated on a barstool at the far end, you’d spot a young, struggling Jack London, peddling newspapers to make ends meet.

When Jack was seventeen, he shared his dream of studying at the University of California and pursuing writing with owner Johnny Heinold. The story goes that Heinold paid for Jack’s first–and only year–at the University; college was not in his spirit, but writing was. He wrote fifty-three books in seventeen years, outselling Mark Twain during his time; and his mentor and lifelong friend, Heinold appears in a couple of them; “John Barleycorn” and “The Tales of the Fish Patrol”. Stories from the saloon’s shipmates and patrons fueled other tales; i.e. Call of The Wild and The Sea Wolf. Although he passed away from kidney failure at 40; his novels did not. 

A few years ago, during the intense period of ‘statue removing’ and ‘whitewashing history’ that captivated the media and, by extension, our entire nation; Jack London Square—specifically the statue situated on the waterfront—became a significant point of debate and discussion. Many voices weighed in, and emotions ran high. Fortunately, this contentious idea faded away almost as quickly as it appeared, like a fleeting trend on Instagram. Today, the square continues to stand proudly as a tribute to the influential writer, celebrating his legacy and contributions to literature and culture.

Heinold’s gained its “First and Last Chance” nickname as it was the initial and final stop for sailors embarking on extended trips or toasting their homecoming, seeking liquid bravery before and after their maritime adventures.

They do not serve food at Heinolds but make an incredible Bloody Mary. Koh, our bartender, was funny, friendly and welcoming. He leaned over the bar and in a conspiratorial tone, made his first lunch recommendation; “It used to be an old brothel. You’re going to love it.” 

Heinold’s Tavern kicked off an unexpectedly delightful four-day adventure in Oakland’s vibrant Jack London Square district.

Koh’s Recommendation: The Fat Lady Bar & Restaurant

Koh did not lead us astray. The Fat Lady is eye candy from the onset; elegant, chic, and Victorian, featuring Tiffany lamps, colored glass, dark wood, red velvet wallpaper, gold-framed art, signs, and more.  Picture an adult version of Farrell’s (with drinks instead of milkshakes) but dimmer. Many items are awash in history. For example, the back bar traveled around Cape Horn in Victorian times and was once used in Mike’s Pool Hall in San Francisco, some beer signs came from old breweries, and the exit sign was salvaged from San Francisco’s long-gone Fox Theater.

The Fat Lady got her name from a painting of an unclothed woman, originally from the famous Overland House tavern in Oakland, a spot Jack London frequented. This artwork now graces the bar inside The Fat Lady.

I was craving a burger and fries. We sat at the bar, chatting easily with the bartender. I couldn’t find a burger on the menu. We got up to leave—and this is when The Fat Lady went above and beyond, outshining any service we’d experienced in recent memory. We heard someone call out and footsteps behind us. We paused and turned. Was something wrong? What happened? Could they help?

“I was hoping for a hamburger,” I explained hesitantly.

“We have a great hamburger on our menu. Right here,” she said, pointing to the menu she’d brought outside.

“Perfect. Let’s go back inside,” I replied. And we did.

As we were re-entering, a patron at the bar advised: “You don’t want to leave. The food here is great.”  He was right. We ate our burgers in stylish elegance coupled with cocktails crafted with care.

Koh’s 2nd Recommendation: Sláinte Irish Pub

Sláinte (pronounced slawn-cha), is Gaelic and it means “Cheers”; which is exactly what this Irish pub is: a place with heart, warmth, and a wonderfully welcoming spirit. Which is probably why we went there three times in four days, with friends in tow. It would have been four days; but, they are closed on Mondays.

Sláinte opened in 2017, aiming to create an authentic Irish pub. Six short years later, she announced it was closing.

During the farewell period, former employees Joe Lee and Edward Bustos visited. They jokingly texted Gallanagh, asking where she was. Her unexpected reply was, “You want to buy a pub?” Their response was, ‘Maybe??’.”

Contracts were signed, hands were shaken and just 6 weeks after its “official” closure, Sláinte reopened.

We ate so many things and drank even more. We loved Joe and Chantelle and the crowning achievement for me was my favorite cocktail prepared to perfection: a gleaming glass, filled with a rich amber liquid that catches the light just so, crowned with a plump, glossy Luxardo cherry. This, my friends, is the epitome of cocktail perfection. 

The Manhattan is history in a glass. Legend has it that The Manhattan was born in the 1870s at the Manhattan Club in New York City, created for a banquet hosted by Lady Randolph Churchill, Winston Churchill’s mother. Whether this tale is true or not, I don’t know, but over the years, The Manhattan has been loved by many. Frank Sinatra was known to enjoy a Manhattan or two, and it’s said that Marilyn Monroe learned to make the perfect Manhattan to impress her then-husband, playwright Arthur Miller. So, I feel like I am in good company!

The Cellarmaker/Nido’s Backyard and The Plank

We walked by open aluminum garage doors that invited us into the spacious, warehouse-style Cellarmaker, which used to be a Blue Bottle Coffee. A San Francisco institution with Detroit-style pizzas and a dizzying array of beers, we had to stop in for both. Cellarmaker has been around for over 10 years and has created over 600 unique beers of which 250 are IPA’s. But, what is Detroit-style pizza? It is a rectangular pan pizza with a thick, chewy, caramelized cheese crust. Yum! We dug Cellarmaker.

We then ventured to Nido’s Backyard. This open-air spot boasts vibrant wall art, desert plants, and twinkling lights. We sipped pricey drinks amid a crowd that felt too youthful and glued to their phones for our taste. To us, Nido’s seemed Mexican in name alone, lacking an authentic atmosphere.

The Plank in Oakland offers bocce, bowling, arcade games, dining, and drinks. It’s massive, but the service is terrible. We sat down but got no attention. I had to order at the bar three times. Given the poor experience, it’s not worth the cost.

The Marina or The Good, The Bad & The Ugly

We enjoyed four delightful days at Jack London Square Marina. Each morning, sunlight coaxed us out of bed, and we had fun exploring the area and sampling local drinks—but only during daylight hours. Oakland’s reputation for crime is widespread and well-known.

With nearly 500,000 residents, Oakland’s crime rate reflects ongoing economic struggles and social issues. Tree-lined streets feature many closed businesses, some with handwritten notes citing safety concerns as the reason. Realtors use Crime Maps to show potential buyers local criminal activity. Crime is indeed rising. 2023 had the highest assault and murder rates in two decades. While 2024 may see a slight dip in these crimes, robberies, home break-ins, and car window smashing to steal valuables are now most common.

This brings me back to the Marina, nestled in Jack London Square among upscale restaurants and breweries. The Marina itself is rough. Break-in signs are everywhere—locks removed from doors, restroom grates kicked in, and the washing machine secured behind two locked metal gates, each needing a different key.

The device likely functioned properly, but I couldn’t find quarters anywhere nearby to use it. No banks were around. Eateries, shops, pubs—even the harbor lacked quarters. I proposed the marina stock quarters for visitors, to which they readily agreed. As for me, I abandoned the laundry plan. I’ll have better chances in Morro Bay.

The showers and bathrooms presented a completely different set of challenges. They were consistently wet, grimy, and utterly repulsive. It remains a mystery when they were last cleaned, if ever. It’s advisable to wear flip-flops to protect your feet from unsanitary conditions. It seems likely that there is a lack of staff to maintain these facilities.

Now, let’s talk about the staff: they were truly remarkable. Despite being overworked, often overlooked, and facing an uphill struggle, they remained helpful and friendly even amidst the decay and crime surrounding them. Their dedication was evident, making the situation a bit more bearable for everyone involved.

Following our four-day stay, encompassing our San Francisco adventure, we departed the Bay, heading towards Half Moon Bay–an exciting prospect for us. Overall, our time at Jack London Square proved to be a positive experience.

Until Next Time!

Fear Less/Adventure More!

S/V Gypsea Explorer 

Me & The Kiwi

 And–here is Our 24 Hour in San Francisco Post.

5 Songs Inspired by This Trip!

“Baby Got Back”—- Sir-Mix-a-Lot

 “Oakland Stroke”—— Tower of Power

“U. Can’t Touch This”—–M.C. Hammer

“Slow Hand”—Pointer Sisters

“Made In America”— Del the Funky Homosapien

And, if this tickles your propellor, grab Amazon Prime Music Here–FREE!

Explore My Amazon Store and uncover a world of music, sailing essentials, and specialty items you won’t find anywhere else. Your next favorite find is just a click away!