8 Great San Francisco Spots to Lose Your Hat

“I left my heart in San Francisco.”

— Tony Bennett

“I lost my hat in San Francisco.”

— Charles McCool

After losing my hat in San Francisco, and realizing I would not see it again, I sang (in my head) variations of Tony Bennett’s classic song.

“I left my hat in San Francisco.”


“I lost my hat in San Francisco.”

Oh, by the way, losing my hat (or losing your hat) is not a euphemism. I really lost my hat.

I think I know exactly where I lost my hat.

It was a gorgeous San Francisco day, wonderful temperature for walking. I brought along my sweatshirt and hat; to be prepared for weather changes and because it was slightly chilly when I set out. During my few hours walking from my lower Nob Hill hotel, through Chinatown and North Beach, up Lombard Street to Coit Tower, and up and down the steep San Francisco stairways, I removed my hat and sweatshirt several times. Each time I removed or put on my sweatshirt or hat, I opened and closed my backpack.

Coit Tower, San Francisco
Coit Tower, San Francisco

Well, you can imagine how I lost my hat. It fell out of my backpack.

I last wore my hat walking up the Filbert Steps. Somewhere during the steep ascent, I stopped to take pictures (and catch my breath) and stow my sweatshirt and hat when I got too warm. Then I got cool along the relatively flat walk on Montgomery Street toward the Transamerica Pyramid building. At the Vallejo Steps I put my sweatshirt back on. I did not put on my hat because the sun was out and felt good.

My hat either fell out of my backpack when I took pictures on the Filbert Steps or when I took my sweatshirt out of my backpack at the Vallejo Steps. So, that is an excellent first place on my list.

Vallejo Steps, San Francisco
Vallejo Steps, San Francisco

8 Great San Francisco Spots to Lose Your Hat

  1. San Francisco Stairways. You will exert yourself walking up and down the steep San Francisco stairways. Be careful with the opening and closing of backpacks, so that you do not lose your hat (as I did).
  2. Ferries. A ferry ride in San Francisco Bay will provide beautiful views of San Francisco, Alcatraz, Angel Island, Bay Bridge, Golden Gate Bridge, Marin Headlands, and more—but hold on to your hat. Golden Gate Bridge and sailboat in San Francisco bay
  3. Golden Gate Bridge. Walking or biking across the Golden Gate Bridge is a San Francisco treat. It is usually very windy, though, so you can easily lose your hat.
  4. Cable Car. Leaning outside a cable car is something everyone simply must do. When the cable car is in motion, especially going around a corner, is prime time for a loose fitting cap to go flying off.
  5. Municipal Pier. Views of the city, Alcatraz, and the Golden Gate Bridge are fantastic from the Municipal Pier. Just like being on a ferry or the Golden Gate Bridge, though, it can be windy so mind thee chapeau.

    San Francisco Municipal Pier
    San Francisco Municipal Pier
  6. City Lights Books. City Lights does not require patrons to remove their hats. The store has eclectic collections including sections on Beat literature, Muckraking, Dada and Surrealism, and Spiritual Traditions. You will want to remove your hat to allow your head to breathe. If you lose your hat in City Lights, you may have left it on this chair. City Lights Books, San Francisco
  7. AT&T (Giants) Park. Many people wear hats at baseball games. Be careful trying to catch a foul ball or home run with your cap. Ever try that? Oh, and if you are sitting near the top row, I guess your hat can became a flying object.SF Giants park sign
  8. Your hotel room. OK, so you can forget anything in your hotel room when packing to leave. Did you know the items most frequently left in hotel rooms are chargers? McCool Travel Tip: I ask at the front desk to borrow a charger before buying a new one.

I did not discover my hat was missing until I was leaving the Ferry Building an hour later. This was the second hat from White Sands National Monument I have lost. The other flew off my head while I was on a bridge on a hike in remote Virginia.

Should I buy another White Sands hat, assuming third time’s a charm? 

Where have you lost a hat?

Looking for an inexpensive downtown San Francisco hotel?

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2 thoughts on “8 Great San Francisco Spots to Lose Your Hat”

  1. Just made me nostalgic of my trips to SFO. I love running at Chrissy Field with the view of the bridge.

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