Cold Pirates & Casinos

As the weekend arrived it was time for the yearly iteration of Tampa Gasparilla - the pirate invasion. This time however the weather was floating around 40 degrees which meant it was going to be a chilly party for those accustomed to Florida weather. On the water the gusts were so strong that they even changed the invasion (boat path) to be less on the open water.

As this would be my 2nd Gasparilla ever this time Alyson and I attended a friend's party near the water so we could experience the arrival of the boats instead of the parade on the ground. While entirely possible to do both, the brutal cold temperatures convinced us to stay to a party that was inside/outside.

I don't have previous experiences to draw on, but the amount of police boats on the water was crazy. Some of the city names of the boats were from cities 2 hours away. I guess with a fancy pirate ship being towed they had to have plenty of police surrounding the ship to keep everyone safe. Though hearing from other locals around me - usually the cops are outnumbered, but it seemed most boaters skipped this year due to dangerous wind and cold.

So as we waited on a windy dock we could hear the helicopters and cannons being sounded - the boats were finally arriving. As the boats neared us cannons and people fired beads back n forth between boat and land. Plenty of beads went right into the water, but that must be why divers are out there the next day cleaning up the bay.

This experience is probably way more fun without heavy wind, freezing temperatures and an occasional drizzle of rain. Though no matter how cold it was there was still a dedicated following of parade attendees in not enough clothing for the weather. The idea of a large party once a year probably convinces most people they can handle any weather situation.

For us after early drinking and getting whipped by the cold wind and rain - we started our journey back home around 4:30pm to recover for our activity of the next day. We were heading to the casino for a bit of gambling and steak.

Now for me a visit to the casino was a 1st time experience so we went with $100 in cash as our first journey together prior to a early dinner celebration. We wandered around the smoke-free section to find some empty slot machines and stumbled upon an area that had plenty of open machines.

We sat down and put $10 or $20 in both our machines and saw the $1 and predicted that would give us 10 or 20 spins. Quickly we learned we were in a high roller slot section as each spin was taking $10 or $20 per button click. However, since we only put that much money in - we both lost all that money in one button click right out of the gate. Now I understood why someone offered to get us a drink the instant we sat down. I should have watched a YouTube video to understand the credits, denominations and different type of slots available because I was clearly confused with how a $1 bet could cost $20 for a single spin.

With the embarrassment over we left that section and wandered around to find some cheaper slots so we could kill some time with more than a single button click. As we found a different slot machine I quickly realized the pattern at play - I'd click the button a few times and get nothing and right before my credits were gone I'd get a win that would bring me back up.

It was almost like clock work that my spins near $0 would net me the biggest return, so once I turned $20 into $45 I left that machine. It blew my mind how fast you can lose money, but also how fast you can gain it. I could click a button and lose $9 in 3 seconds, but watch an animation for 15 seconds that gave me $60.

Meanwhile a guy next to me would skip every single animation whether he was winning $500 or approaching $0. Some people just looked so brain fried just mindlessly drinking and clicking a button. I also was curious how people were spending so much money without a care in the world - I felt icky just bringing $100 that I was planning to lose, but could watch a random person load in a thousand dollars and lose it in a minute.

I cashed out slightly ahead and we wandered closer to our dinner reservation and continued losing and winning money. When all said was done as we walked into dinner I had $77 in winnings, but had brought $100 to the casino so overall (-$23) net negative. I was excited though to have another steak experience at Council Oak inside the casino. It was the 5th best steakhouse we voted during our 2025 steak research & blog.

Though much like last time I hated having to be in the smoking section on the journey to the restaurant. For a non-smoker the air was so disgusting and I just felt dirty breathing the air full of 2nd hand smoke. Thankfully once we entered the restaurant we had a clean separation from the main floor and the air quality was cleaner. I felt bad for any employee who didn't smoke and was forced to work in that area.

Alyson and I split a salad and French Onion soup and both of us went with fillets this time around. I just wasn't full enough to get the smallest rib-eye size which was 24 ounces of meat. Like expected at a high end steak dining experience the steak was cooked perfectly to my liking and paired with a strong horseradish sauce.

I was happy to finally have a strong horseradish sauce that rivaled the strength I can do at home. With all the wine and bread we enjoyed though for the first time in awhile I could not finish my entire steak. So we went home with some leftovers and turned our winnings to cash.

We left with less money than we showed up with, but physiologically we were as low as $14 at one point - so to leave with $77 was something to be proud of. Though knowing the casino never loses it'll be years till we come back for another special occasion. I'm lucky that neither of us are drawn to the casino, because it seems like such an easy place to lose hard earned money. Either way I was happy to understand a bit more on how a basic slot machine works after a bit of trial and error.