My free parking dilemma

After two months of adjusting to a new addition, we’re back on the road again. No flying, but after a two hour drive we’re in our favorite local weekend destination: Portland, Maine. We’re back at the Hyatt Place Old Port (no suite though this time), and even if the rest of the weekend is a bust I’d already consider this trip a success. I’ll have more on that later, but wanted to write a quick post about a random “issue” I have.

For some reason, I have a major philosophical opposition towards paying for parking. It goes beyond just saving money, I think, I just go very far out of my way not to pay for parking at all. I’ll circle in Chinatown for 45 minutes before paying $10 to park in a garage.

How this relates to our trip to Portland is due to the $18 valet parking charge at the Hyatt Place. Last time we were here we arrived on Saturday and stayed on Sunday and Memorial Day, so I was able to street park for free after 6 PM. Arriving on a Friday night, I’m going to have to deal with parking all day tomorrow.

Still, I refused to pay the $18 for the convenience of parking. I hate valet parking in general, since I like having access to my car immediately. Though you can see the foolishness in that kind of thinking since I can’t have my car immediately if it’s parked on the street blocks away.

Instead of paying $18, I’m going to move my car all throughout the day tomorrow, probably paying about $10 in parking altogether at meters. Now that I’m typing that out it seems even stupider that I didn’t pay for parking, and that’s not even including the fact that I’m risking a ticket if I don’t get back to my car in time.

Theoretically, I feel like chasing these tiny dollars, especially when it comes at the cost of a ton of convenience and with a decent amount of risk, is completely stupid. In practice, I just can’t bring myself to pay the parking fee. Am I crazy? Do other people treat paid parking in a similar fashion? Or are there other areas where you save a few pennies even though it’s basically irrational? I’d love to know.

Oh, and I should add, I blew all the money I saved on parking on like, four oysters. Delicious, though.

Just an average joe trying to fly his family for less

18 thoughts on “My free parking dilemma

  1. I’d argue that this falls right in the “$10 Rule” area… Its so small a cost that you would probably get greater value from paying it and having that peace of mind… But, I couldn’t imagine myself in your position, even if I tried.

      1. Is your time in doing all this not worth $8-$10 for the time you could be spending with your family and the peace of mind of not having to worry about the car? I would pay the parking fee whenever I am travelling just for that. Money is not everything. One of the reasons I pay especially in a busy city are the in/out privileges of parking in a hotel lot.

          1. Ahh, Yes. Must be an Asian thing (Not being racial or stupid here, I am one myself). Our an predecessors have taught us when growing up about saving money and it can get in-grained in you. Heck, my relatives would take the train by using an unlimited train pass, swipe once, than wait 20 minutes before the second person gets on or they would walk to the train station to swipe another relative in and walk back home just to save the train fee.

  2. I do the same stuff – my piece of mind is knowing i got the best deal possible. Rarely i will take the costly yet easy way – usually after a few drinks

  3. I agree with you on not wanting to pay for parking. I live in the suburbs, and it’s very rare that I pay to park anywhere. In this case, I’d just pay the money to park just for the peace of mind. It’s not worth risking a ticket a paying more or your time. A few weeks ago, I had a weekend trip planned to Chicago. I was using points to pay for the Radisson Blu, booked pre-devaluation. Though the hotel was free, I had to pay $50 a day to park. I really didn’t want to spend $100 to park my car. So, I ended up taking the train to avoid paying parking, then just used Uber in the city. It was 3,000 UR points roundtrip which I thought was a great value. The train departed at 5:13 a.m. which was not fun, but still a great experience for my kids.

  4. Having grown up in Portland and as someone who still goes back three or four times a year, I’d advise you just pay the $18. Parking enforcement in the Old Port is pretty darn efficient, and if you are only saving $8 or $10 per day it just doesn’t seem worthwhile. I start getting stressed at the 90 minute point (of a 2 hour meter) and then moving and finding a new spot isn’t easy on busy weekends – so you are either dealing with your car or thinking about your car roughly half the time you are there.

    That said, I agree with you, I hate paying inflated hotel parking fees – usually I’ll taxi or train in from an airport and then rent a car from a city rental office just for the day/days it really is needed. But obviously you drove to Portland, not an option for you.

  5. For small.charges, think in terms of miles. It gives you peace of mind. Instead of thinking you saved $10, think you saved 1000 ur points. People go out of their way to earn/save 1000 points. 1 million posts have been written about CSP FIRST Fridays which would earn you hardly 1000 ur points in a lifetime. Congrats on saving 1000 points 😀

  6. The stress ain’t worth the money . Usually when someone says ” it’s the principle ” , there ain’t no principle . It’s just an excuse to beat themselves up and make life harder . When you finally decide that you’ve suffered enough , pay the money and get on with your life . You can’t get more time .

  7. Not me, so much. But Husband, absolutely. For the first five years that we regularly attended the Gopher volleyball games–there’s one tonight, whee–he would crab about paying for parking near the Athletic Center. And, of course, if there was a men’s basketball game, or a men’s hockey game going on at the same time, the prices jumped, as did his complaints.

    Every time, I would point out that he should consider paying for parking just part of the cost of attending the matches. And, if that made the cost too high, he should stop going. It took five years, but it finally sank in.

    Maybe, you could start doing something similar. Know ahead of time that parking (or valet parking) costs X. And if you decide it’s too much, you can always skip the trip. With a wife and two tiny kids, you really are doing ALL of you a big disservice by causing such delays, because it cuts into the precious time you have together, just to save $24 for an entire weekend. Holy cow, Joe! Skip three glasses of wine for the entire w/e, and the extra cost is paid for. AND you have a whole lot more time with the wife and the kiddos.

    1. I already said it was a bad idea 🙂

      But yeah, ended up working out this time because we decided it was easier to drive to our destinations vs. pushing two strollers, so very little stress was added. Doesn’t mean it was the right decision last night, but sometimes bad decisions work out. Even broken clocks are right twice a day. But yes, probably won’t do the same thing next time, but hey, don’t gotta worry about anything tonight or tomorrow parking cost wise so that’s next time’s problem!

  8. So after 6pm on Saturday, you didn’t have to feed the meter anymore? Were the meters in effect all of Sunday or only free after 6pm? I’m planning a trip there and I have my eye on the HP, but it’s the parking that’s holding me back! I had the same headache when we drove to DC (also arriving Friday). I’m Chinese myself so this has to be an Asian thing haha!

  9. I hear you, believe me. In this case, time is golden, you got two little ones to be with, give your self a rest with your car next time. Enjoy your family time! Gorgeous weekend for you. Have fun.



    1. Had a thought. Cultural mores are hard to overcome, certainly. But every culture has dictates about the importance of family. Maybe you could allow THAT one to override the “Don’t spend a penny you don’t have to on non-essentials.”

      Which, for all of us, becomes some nutty version of that. Mine isn’t parking. But you haven’t used up a tube of toothpaste, or gotten the last drops out of a bottle of shampoo, unless you do it with the singlemindedness that I do!

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