The Key West Mystique

Key West Island News


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Key West Parking Sticker October in Key West

Key West parking stickers | The coveted island badge you just have to have

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


Let’s get the headline out of the way first: If you’re reading this on Saturday, Oct. 30, in the Key West Citizen, you have one more day before your residential parking sticker expires. Technically. You’ve got two choices: Panic and head to social media for an outrage festival. Or, go back to the coffee and weekend chores and forget all about it.

I’m opting for choice two. Sooner or later, Key West’s lovely neon hot pink, residential parking window sticker will arrive in the mail, Ranger Ed will slap it on the windshield and we’ll be good to go until Oct. 31, 2022, when we do this all over again.

The Key West residential parking sticker is a coveted island perk. Always a colorful design, the sticker is an at-a-glance visual clue that one belongs here. It says the vehicle is owned by someone who has made a long-term commitment to the island of Key West. Some folks opt out of removing old stickers, lining them up in a conga dance up and down the windshield. We wear those stickers with pride — and we get some free parking to boot.

Key West Island News

Other than the occasional critical sniffing at the annual design changes or the whining of off-island drivers who aren’t eligible for a residential sticker, the annual parking sticker purchase was a non-event. One walked into the Monroe County Tax Collector’s office at the corner of Truman and White, showed proof-of-residence documents, paid $20, was handed a sticker and off one went.

Until this year when Monroe County cut loose the City of Key West and said “Parking stickers? You’re on your own, my friend. We’re not doing it for you anymore.” Why? Honestly, I didn’t bother to ask because (a) it doesn’t matter; and (b) it’s probably because the county didn’t want to foot the bill for handling walk-in sticker seekers for what is clearly a city-only service.

Pretty much at the last minute, Key West was left to scramble for a solution. I can empathize with the “Oh-Crikey” moment when the city parking folks learned their worlds were about to get, well, messy. Nothing like a parking brawl to get locals tuned up on social media.

The city turned to Passport Labs Inc., a Charlotte, N.C., company specializing in parking solutions. Passport manages the Key West smartphone parking app, which works pretty much flawlessly these days. I use it regularly, including for the free parking in the designated lots. (For those who remember the early, not-so-user-friendly days of the app when the free locals parking didn’t work, they’ve fixed that.)

Passport, working with the city, quickly launched an online residential parking permit registration system — and all, well, heck, broke out. First up in a series of Mary-Joseph-and-the-Wee-Donkey moments: No stickers. Let the brouhaha begin.

How to improve the Key West parking permit registration next year

I was all for doing my permit online, even with cumbersome scanning and uploading documents. But no stickers? How were the ticket writers and tow-ers going to tell who was parking in residential-only spaces? We will check license plates came the answer from the city. I beg your pardon? With stickers, one can quickly figure out who was parking illegally. Without stickers, enforcement was clearly going to be a nightmare. Within days, the stickers were back and folks calmed down.

Until they tried the new online registration system on Oct. 1. First, one has to be online savvy and one must have the equipment — documents have to be scanned or photographed first. Not everyone has a scanner. Smart phone photos are so huge the Passport software has trouble digesting them. Not everyone has access to a workable device. The user interface is cumbersome, clunky and not particularly intuitive. (Note to Passport and the city: For next year that UI needs a redesign and better quality assurance testing.) And, then there’s the sticker shock: What we thought was a $20 permit costs $39.13 because of online fees.

Perhaps the biggest challenge was the lack of information on troubleshooting the system, on whether there were in-person alternatives and how long everything would take. The how-to info that is available on the registration site is sketchy and confusing. That’s an easy fix for next year.

A few days into October, the city quietly started issuing permits in person at City Hall. From all reports, it was a quick in-and-out. Next year that needs to be an option. I’ll gladly stick with online, but the online application should allow me to renew without having to upload duplicate documents. Simply pay for the renewal permit to be mailed — or let me stop by City Hall before (set a deadline) and pick it up.

I figured it out and got the email saying I’d be notified when my permit was approved and then I could pay. It would have been nice had the email said that could take three weeks. I got the “you’re approved” email and I paid. Those various auto-generated emails will need a serious re-working for next year.

The window sticker is supposedly going to arrive “next week,” which could mean it’s in my mailbox as you read this. Or it could fall victim to the ubiquitous delivery delays. I’ve been assured parking enforcement will cut me some slack until the new decal arrives.


  1. Lou Lou Mcintosh

    Are you still able to use the passport app for your 4 free hours .

    • Linda Grist Cunningham

      Yes. In designated lots and for local residents who have purchased a city parking permit.

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