Celebrating Financial Freedom: My Trip to San Fran

the Golden Gate Bridge

Selfie at the Golden Gate Bridge.

A promise I made to myself when I burned my mortgage was that I’d stop putting off travel and make it more of a priority. With my mortgage paid off, I no longer had a good excuse not to travel.

As I mention in my book, the best part about achieving financial freedom is that it gives you choices. You don’t have to stay at a job that you hate just to pay the mortgage. You can “seize the day” and do what matters most to you, whether it’s starting your own business, volunteering or travelling.

Going forward I plan to take at least one big trip a year. My inspiration for travelling is my uncle. For years he dreamed of taking a vacation to Europe with my aunt. He put it off because he was busy with life and raising a family. When my uncle and aunt both retired, they decided the timing was finally right to take their dream vacation.

My uncle’s trip was going great, until partway through when he started to feel pain in his stomach. He didn’t want to ruin the trip, so he ignored it. When he got back to Canada, the pain was excruciating, so he went to the hospital – and found out he had cancer. Sadly, he passed away six short weeks later.

Our health is something many of us take for granted. In memory of my uncle, I plan to travel the world while I’m still young and in good health and go on the trips he wasn’t able to.

Why San Francisco?

I knew I wanted to go somewhere to celebrate burning my mortgage, but I had a tough time choosing my travel destination. I narrowed it down to three places: Vancouver, San Francisco and Europe. In the end I chose the Golden City, San Francisco. I went with San Fran for a couple reasons. I was familiar with California, having travelled to San Diego for FinCon last year. Secondly, I made some friends at FinCon who were gracious enough to offer to show me around town. That sealed the deal. San Fran, here I come!

Planning My Trip

The continental breakfast at my hostel.

Once I settled on San Fran, I started planning my trip a couple months in advance. Since I have a PC Mastercard, I booked my flight through PC Travel. The airfare was comparable to Expedia. I even got bonus PC Points for booking a flight with Air Canada. For a roundtrip flight I ended up paying just under $700.

When I travelled to San Diego, my most costly expense was my hotel. Since I was travelling solo, to help save money I did some travel hacking and stayed at USA Hostels. I went with the most affordable option: a four-bed mixed dorm room for less than $60 a night. (A lot better than spending $200 a night on a hotel!)

This was my first time staying at a hostel, so I didn’t know what to expect. Luckily, I was pleasantly surprised. My roommates were very considerate. They went to bed at a decent time and didn’t make a ton of noise. The hostel even included a free continental breakfast with raisin bread, English muffins and pancakes – yum! If you’re looking for a hostel to stay at in California, I’d highly recommend USA Hostels.

One of the main reasons I decided to visit San Fran was because of Alcatraz. I heard from family and friends how much of a unique experience it was. I assumed the tickets worked similar to attractions like the CN Tower – you order your tickets a few days in advance. Big mistake! When I went to order tickets to Alcatraz, it was sold out for the next two month. How disappointing! (My best advice is to book your tickets as early as possible.) Since Alcatraz was sold out, I ended up buying tickets to the San Francisco Bay Cruise instead for $29. I also purchased discounted tickets to the Aquarium at the Bay.

Since this was my first time to San Fran, I wanted to make sure I didn’t miss any of the sights. I’m a big fan of tour buses. They’re a great way to meet people and see the sights of the city. I bought tickets to the Big Bus San Francisco Hop-on Hop-off Tour for $45.

Day 1: Wednesday, July 26

The view from Coit Tower overlooking the Bay Bridge.

The first day was a long day. My flight left at 8:15AM ET from Toronto, so I had to wake up at the crack of dawn – 4AM. Oh, joy! I ended up making it to the airport with plenty of time and boarding my flight as planned. The flight lasted about 5 hours. Due to the time zone difference, I arrived in San Francisco at 10:25AM PT.

Similar to Toronto, the airport in San Fran is far away from the downtown. I had several options: I could take a taxi, airport limo or BART (short for Bay Area Rapid Transit). There is a subway stop conveniently in the airport, so I chose BART. For less than $10, I found myself in downtown San Fran in less than half an hour.

I started my San Fran adventure of Market Street. This was unlike any street I’d ever seen. It’s lined with buildings with beautiful architecture. Vintage streetcars run down the centre of the street. It has a mix of financial institutions, restaurants and shopping.

After having lunch and exploring the downtown, I met up with my friends for a tour of their offices. Once the tour was over, they were kind enough to take me out to one of San Francisco’s finest restaurants. After enjoying some good food, my friends promised to take me to somewhere with a spectacular view. After traversing some of San Fran’s steepest hills and climbing a staircase that seemed to go on forever, we made it to Coit Tower. Despite the fog, this offers some of the nicest views of the bay.

Day 2: Thursday, July 27

In front of the Golden Gate Bridge.

The boat cruise didn’t leave until 11:15AM, so I took some time to explore San Fran. I walked along the Embarcadero, a beautiful boulevard that runs along the bay lined with palm trees. I stopped by the Ferry Building Marketplace and spotted some sea lions bathing on Pier 39.

I’ve been on boat cruises before, but nothing quite like the San Francisco Bay Cruise. It took us around Alcatraz Island before sailing underneath the Golden Gate Bridge. The views were spectacular, but a word of caution – be sure to dress in layers. San Francisco is pretty chilly to begin with. It gets pretty windy on top of the boat.

After the boat cruise, I spend the afternoon at the Aquarium at the Bay. This was the first aquarium I’ve ever been to. It’s certainly worth a visit, since it’s a non-profit aquarium with an important mission: to inspire conservation of the ocean.

Day 3: Friday, July 28

The San Fran Cable Car Museum is worth the visit – and it’s free!

Since I’m a bit of a transit nerd, I started my day by visiting the Cable Car Museum, a free museum dedicated to, you guessed it, cable cars. It was interesting to learn about the history of cable cars in San Francisco and see how they’re pulled along the streets.

After taking a cable car ride to Fisherman’s Wharf, I hopped on the Big Bus San Francisco Hop-on Hop-off Tour. I visited the best sights San Fran has to offer, including the Painted Ladies (the houses featured in the opening of Full House), the crookedest street in the world, Lombard Street, and the Golden Gate Bridge. Walking over the Golden Gate Bridge was breathtaking. It offers perhaps the best view of the bay (just be sure to dress warmly).

Day 4: Saturday, July 29

Ocean Beach in San Fran.

Saturday was my last full day in San Francisco, so I wanted to make the most of it. I went for a walk to the AT&T Park where the San Francisco Giants play. After that I went for a stroll in the Mission District and popped into Dandelion Chocolate to sample their chocolates and try out their Italian hot chocolate (warning: it’s super rich). For lunch, I bought a vegetarian burrito at La Taqueria, which claims to have the best burrito in America (it didn’t disappoint).

After renting a bike for $25, I spent the afternoon biking through Golden Gate Park. Situated near the Golden Gate Bridge, it offers everything from waterfalls to bison. At the end of my one hour bike journey, I found myself at Ocean Beach, overlooking the Pacific Ocean.

Final Thoughts

I had a wonderful time in San Francisco. I’d highly recommend visiting. If you decide to go, dress warmly. San Francisco is a city with a microclimate, so the temperature barely cracked 18°C. It gets chilly at night, especially with the wind, so wear a sweater or windbreaker. I didn’t get to see Alcatraz, so I’m sure I’ll be back to the Golden City one day.


Sean Cooper is the author of the new book, Burn Your Mortgage: The Simple, Powerful Path to Financial Freedom for Canadians, available at Amazon, Indigo and major bookstores.