My Encore Trip to San Fran

Alcatraz jail cell
Alcatraz jail cell

I’m not going to lie. I love California! I’ve visited it the last 3 years. My favourite city without a doubt in the Golden State is San Francisco. I don’t know if it’s the Katy Perry “California Gurls” song or the vintage trolley cars, but there’s just something that draws me to my “home away from home.”

When I went to San Fran last summer, my biggest regret was not seeing its main attraction Alcatraz. Visiting Alcatraz is something high up on my bucket list. I made the mistake of assuming I could buy tickets to Alcatraz a month in advance. Oops! The tickets were sold out until the fall. I took the boat cruise around Alcatraz Island, but it wasn’t the same.

Well, as the old saying goes, fool me once, shame on you; fool me twice, shame on me. (At least I got this idiom right, unlike George W. Bush, but I digress). I didn’t repeat this mistake. I booked my Alcatraz ticket three months in advance. Since I’m not in San Fran every day, I splurged and bought the super duper Alcatraz Behind the Scenes Tour.

Alcatraz
This quote is Alcatraz in a nutshell

I’m already pretty familiar with San Fran, so booking my flight was pretty straightforward. I also booked a flight from San Fran to Los Angeles. I’ve heard so many interesting things about L.A., so I figured I might as well check it out. Hiking up to the Hollywood Sign is also on my bucket list.

I considered taking the bus from San Fran to L.A. to save money and avoid the hassle of airport security, but when I found out it would take 9 hours on a good day, I decided against it. (Something it’s worth spending the extra money. Besides I had limited time in California.) I’ve always wanted to take the Pacific Coast Highway, as it’s known for being one of the most scenic routes in the world, but I figured it wasn’t worth being stuck in the rush hour traffic for hours in L.A.

Day 1: Tuesday, November 6

Coit Tower observation deck

Similar to last time last time, I stayed at USA Hostels. I was happy with my last stay there, so I figured, if it ain’t broke, don’t fix it.

I considered staying at Airbnb because I was planning to work while I was on the road, but decided against it. I’d be paying twice as much to stay in an unsafe part of the city. No thanks! Besides, unlike Airbnb where you might not be able to check in your luggage until 3pm or later, the hostel will watch my luggage all day, even before my check-in time, at no extra charge.

The last time I was in San Fran, one of the first things that I did was hike up to Coit Tower, a beautiful tower overlooking the Bay. Unfortunately, last time the observation deck was closed. Lucky for me, this time it was the early afternoon, so I had plenty of time to head up.

View of the Golden Gate Bridge from Coit Tower

When I made it to Coit Tower, I paid an extra $8 to take the elevator up to observation deck. It was well worth it! The observation deck didn’t look far from the ground, but it gives you a breathtaking 360° view of the city. The open top makes it that much more spectacular!

Afterward, I headed towards the Mission District to meet up with my friends Korrena and Mika for dinner. I picked the perfect night to be in San Fran. It just happened to be U.S. mid-term elections. It was interesting being in U.S. during the elections.

My friends and I dined at a tasty Mexican restaurant called Gracias Madre. It had a nice atmosphere and the food was good, so definitely check it out!

Day 2: Wednesday, November 7

View of the Golden Gate Bridge from Alcatraz at sunset

In the morning I stopped by the Credit Karma offices on Market Street. The offices were just how I remembered them, right down to the life-sized Justin Trudeau cardboard cut-out. (Our prime minister is pretty well liked in California.) I also got a chance to stop by Credit Karma’s private coffee café and get some hot chocolate.

After a delicious lunch at an upscale pizza place on Market Street, I headed towards the piers on the Embarcadero to catch my ferry to Alcatraz. To say I was excited would be an understatement. Alcatraz is America’s most famous island for a good reason.

The ferry ride to Alcatraz is enjoyable and scenic. You get a great view of the Golden Gate Bridge and the Bay Bridge. Be sure to wear a coat (even during the summer), as it gets pretty chilly on the ferry.

When you arrive at Alcatraz Island the first time, the moment is a bit surreal. It’s hard to believe you’re on Alcatraz Island or “the Rock” as the prisoners called it. It may be hard to believe, but Alcatraz Island has history dating all the way back to the American Civil War when it was used as a military garrison.

When Alcatraz was decommissioned as a military base, it became a federal prison in 1934. But it wasn’t just any prison. It was a prison designed to hold the most hardened criminals. The criminals who caused trouble at other federal prisons. Some of the world’s most famous criminals stayed at Alcatraz, including Al Capone and Birdman.

Alcatraz at night

I thoroughly enjoyed the Behind the Scenes Tour. It was money well spent. The tour guide took us to places we normally wouldn’t get to see, including a tunnel, an underground jail and a special garden with a stunning view.

Most fascinating of all were the stories. To pass the time, one of the guards used to play chess with Birdman. You can also hear about daring escape of Frank Morris, John Anglin, and Clarence Anglin, the only inmates to ever successfully escape Alcatraz.

At the conclusion of the Behind the Scenes Tour, I highly recommend sticking around for the Night Tour. On the Night Tour you can take Alcatraz’s famous self-guided audio tour and hear more fascinating inmate stories.

Day 3: Thursday, November 8

The Rainforest exhibit in the California Academy of Sciences

On  my last full day in San Fran, I didn’t have anything planned, so I decided to wing it. I went to the California Academy of Sciences in Golden Gate Park. The walk through Golden Gate Park is lovely. It’s the perfect place to go for a walk or bike ride.

I had a lot of fun at the California Academy of Sciences. Also at the Academy is the Steinhart Aquarium, home to over 900 fascinating animal species. The Rainforest exhibit with tropical butterflies and birds was pretty cool, too.

You’ll also want to check out the Morrison Planetarium. You can request a free ticket while you’re at the Academy. The Planetarium features the world’s largest completely digital planetarium dome. Films play throughout the day. I watched “Journey Through the Stars” narrated by none other than Whoopi Goldberg (perfect for Star Trek fans).

San Fran at night

Overall, I had a really great time in San Fran. My only regret is that I didn’t have time to visit Sausalito and go hiking in Muir Woods and see the giant redwoods. Oh well, there’s always next time!

I finished off my time in San Fran by walking along the Embarcadero as the sunset. It was the perfect way to end part 1 of my trip. After that I headed back to my hostel to pack up for part 2 of my trip in L.A.


Sean Cooper is the bestselling author of the book, Burn Your Mortgage: The Simple, Powerful Path to Financial Freedom for Canadians, available now on Amazon and at Chapters, Indigo and major bookstores, and as an Audiobook on Amazon, Audible and iTunes.