I’m kinda known for taking impromptu trips. My focus when planning these is on finding great deals— preferably to a destination I’ve never visited. When I saw the last-minute pricing for San Francisco, I booked a solo five-day trip and a rental car with only 60 hours’ notice. You see, I’m making it a point to teach myself how to de-stress about the whole traveling thing, and short-order trips are one way I do that.

Another self-imposed rule of mine is to avoid planning any more than is necessary for the location. I didn’t know what I’d decide to do when I arrived in the City by the Bay, but I was confident there would be plenty for me to explore. Still, one place immediately popped into my mind: Alcatraz, and because of my slight obsession with things true crime-related, I knew you shouldn’t rely on snagging same-day tickets. Therefore, the first (and only) activity I booked before arriving was a tour of Alcatraz Island. There were three options: day, night, or behind the scenes, which combines both tours plus a private guide. The group size is limited to 30 people or fewer— the other two tours each accommodate hundreds.

Fun Fact: Alcatraz Island is a National Park!

You must take a ferry to get to Alcatraz Island. It’s included with your tickets, but be careful where you purchase those. Numerous resellers charge more for the same tours. Alcatraz City Cruises is the official provider— buy your tickets only through their website. The ferry is located at Pier 33, otherwise known as Alcatraz Landing. I’d just spent a day at the infamous Pier 39, so I was familiar with the area— and the necessity to allocate time for parking, which is plentiful but requires payment. Garages, lots, and metered spots are all available. Alternatively, you can use San Francisco’s awesome public transportation system.

It was windy, overcast, and rainy when we departed. I sheltered inside and watched for signs of the island through the ferry’s large windows. Once I caught my first glimpse, I could no longer be content with sitting behind a pane, so I bundled up and headed outside to the ship’s bow.

There it was— Alcatraz Island, waiting to be boarded.

We were escorted through the prison gate and given a glimpse down the dry moat.

Our first destination was the concrete ruins of the warden’s 15-room Spanish-style mansion.

The first super-cool, totally behind-the-scenes thing happened when our guides took us past a ‘No Entry’ sign and into a tunnel.

Tunneling into ‘Little Alcatraz’

We were headed into the New Industries building, otherwise known as ‘Little Alcatraz’, where prisoners had worked and learned a variety of trade skills.

Several of the industries at Alcatraz directly contributed to the military and World War II efforts. Prisoners did laundry for the army and manufactured items such as submarine nets and deck mats for the Navy. They did so for a tiny wage—one that was difficult to spend because Alcatraz was unique among federal prisons in that it lacked a commissary.

Other prison industries at Alcatraz included furniture-making, blacksmithing, glove and clothing manufacturing, and a cobbler shop.

Next Stop: The Alcatraz Cell House

Our private tour of the New Industries building concluded, and we left the building where Al Capone, Machine Gun Kelly, and several other infamous inmates had once worked. It was almost time to visit the main attraction: The Alcatraz Cell House.

We’ve reached the end of part one. Subscribe to be the first to know when part two of my Alcatraz behind-the-scenes special is released.

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