The Legacy of Bay Voyager

Unique Ways to See San Francisco
March 14, 2020
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“It was called Boondocks back in the day. It was the pub where the officers used to go after their shifts an get a drink. Even after they retired, my dad and all the officers would still get together once a week to catch up and reminisce. I would join them and listen to their seafaring stories.”

Captain Charles Jennings, Bay Voyager
Captain Charles Jennings in front of High Dive, formerly Boondocks
Captain Charles Jennings in front of High Dive, formerly Boondocks

Captain Charles Jennings is a seaman through and through. He’s worked on the water his whole life, just like his father and uncle before him, and his grandfather before them. The story of Bay Voyager doesn’t begin with the company’s founding back in 2011. The story starts with the San Franciso waterfront and the captains and crew that have worked it since the city was founded in 1776.

Since the Bay’s discovery in 1769, then the Gold Rush in 1848, ships have been sailing in and out of the Golden Gate Straight nonstop. The port is a hub of innovation and integral to supplying the day to day necessities for American’s living across the United States. Many things have changed over the years; however, the importance of the waterfront, in many ways, remains the same. Fishermen still rise in the early hours of the morning and head out to sea. Tourists still flock to Fisherman’s Warf and Pier 39 to enjoy the sights and ferries shuttle people from port to port.

Cruise ships and tourism have also always played a massive part in the San Francisco maritime industry. One such cruise ship, the SS Santa Maria, was part of the Delta Line and their “M” fleet that took passengers on an epic journey around South America. The course began in the Bay and sailed south, along the Californian and Mexican coasts, through the Panama Canal, round Cape Horn, and back to San Francisco. For two months, the ship island-hopped in the Caribbean and stopped in bustling cities along the way. It was a novel and luxurious trip for the 1970s.

“Circle of Dreams” promo for Delta Line Cruises feat. Capt. Adrian Jennings.

Before every departure, after every return, it was customary for the captain and crew to have a drink at Boondocks, a pub situated at the beginning of Pier 30 in what is now the SoMa neighborhood of San Francisco. The pub is still standing, now called the High Dive, and looks out onto the very pier that the SS Santa Maria called home. While modern high rises and skyscrapers now surround the pub on the city front, when you gaze out the windows that make up the back wall, the scene is nearly unchanged. The Oakland hills gently rise on the horizon with the port visible in the foreground. The blue water of the Bay stretches between the two cities, glistening from shore to shore.

High Dive View of the Port of Oakland, Pier 30 and San Francisco Bay
High Dive view of the Port of Oakland, Pier 30 and San Francisco Bay

Captain Adrian Jennings started working on a merchant ship as an ordinary seaman – the lowest rung of the maritime ladder. Capt. Jennings worked his way up the hawsepipe to captain. His first professional venture into the ocean was in World War II when he left San Francisco and went straight to Normandy on D-Day. After the war, Jennings continued to work on boats, eventually becoming the captain of the SS Santa Maria, touring the world before he retired.

Being a hawsepiper, or becoming a captain without any formal academy training, was an extraordinary feat in the 1940s. It remains so even today. “My dad’s story, listening to his friend’s stories and hearing about the things they did and the places they went, really inspired me to make up my own story.” This inspiration eventually leads to the inception and realization of Bay Voyager.

Captain Adrian Jennings and son, Charles look at the ocean.
Bay Voyager Captain, Charles Jennings and his father Adrian Jennings look at the ocean.

While Captian Adrian Jennings never got to see Bay Voyager in person, his memory is kept alive by the sights that boating on San Francisco Bay has to offer. While navigating out of the Bay, Captain Adrian Jennings would look at the center span of the Golden Gate Bridge to make sure his ship was lined up straight before entering the Pacific. “I look at the northern tower of the Golden Gate Bridge when I’m leaving the Bay. We’d pass under it at different points, but it’s the same bridge.” It’s in this way, charting the same course of his father, and making up his own story, that Captain Charles Jennings honors his dad’s memory and runs Bay Voyager.