I arrived in Key West at 11pm on Friday night after leaving Philly at around 5pm. The flight was $450 and that included the flight from Miami to Key West, which I would recommend opposed to a bus that takes 3 hours. The hotel was the Southernmost resort which consisted of 261 rooms and had 3 pools, a few bars, and was right on Duvall. Checks off all my boxes.

The group had gotten in earlier and wasn’t partying when I got there so I went to sleep and woke up early to go for a run and checked my surroundings. I met up with Evan and we started drinking at the pool where we saw the Atlanta Falcons punter Matt Bosher. Later in the afternoon there was a sunset cruise where I was easily the drunkest person socializing. I have no idea if the following picture was taken there. I literally took 1 picture the entire time.

After the cruise I remember hanging out with the group at some dock bar and then the world’s smallest bar. It gets a bit unclear, but I think the group went different ways and I remember jamming out with some cover band by myself before wandering to the wrong end of Duvall and taking a cab back. No damage done.

Saturday was the wedding so I decided to take it easy… LOLOLOL. Evan and I went to Irish Kevan’s and listened to live music before heading back to the pool where I drank some “light” beer and chatted up the bartender from Philly who I swear liked my style. I was talking to this bro at the bar and we were talking blackjack when he said, “I always split tens”, and we had an immediate bond and advertised the site. There was one dime piece who walked up to get a drink and after some initial chatting I said, “you look great, do you do a lot of yoga and exercise?” She was flattered and I mention it to give some context of how far I was pushing the envelope on this trip. It gets further.

The wedding was at 4pm and I kept it together appropriately. We took a trolley to a very cool part of the beach for the ceremony. You can watch it here.

Ryan and Lindsae were awesome at keeping it short and entertaining. That was a joke obviously as they were awesome with their vows and the entire beautiful ceremony. Huge congrats to the newlyweds.

We then went to a restaurant where at least 5 speeches were given and dinner was well done. The night maintained at Sloppy Joe’s where we were all jamming out to the band and I asked some 50 year old to bed. She had a 22 year old daughter there as well where things could have gotten interesting when she asked where I was the following night. The night concluded at the Green Parrot where I remember not even being able to have a sip of beer at the end.

Monday was spent hanging out with the bride and groom’s family and I’m sure I was already wearing out my welcome (I’m fairly sure this is a joke, but no guarantees). We played bags on the beach and drank by the poolside bar for most of the afternoon. At 8pm I did a shot of whiskey and passed out until 9:30pm where I drunkenly picked Iceland and Peru in an 8 person World Cup Pool where you get 2 teams (I was 8th pick fwiw).

I met up with the group after that where we shot pool, threw quarters into a fish’s mouth, and hung out until 3:30 where we once again concluded at the Green Parrot. Another hilarious part was this total babe with tattoos up half her body asked me to play Foosball and my coordination was so sad that she beat me 9-0. I could barely hit the ball with my men.

Tuesday was a day from hell as my innards were trying to be outards and my body wasn’t having it. The flight went fine and I got back safely.

Now to the fun part because I feel like if I didn’t give enough details to the trip, this part wouldn’t be nearly as fun.

What I Learned From Key West

• Make Money Money – Going to Key West worrying about money would ruin the time. I easily spent $500 dollars on drinks and food for 3 days and I didn’t even eat a dinner on Monday. The hotel is obviously a cash cow.

• The Wild Card – Without a doubt I was the loose cannon. People my age are, for lack of a better word, responsible. They have family’s and it looks inappropriate to rage. I don’t have anyone to tell me not to do anything and I would have to imagine I have the most fun out of anyone there (except maybe Ryan).
• Socializing – Someone there who I didn’t meet the first night, but did the 2nd said, “You’re Tom, the guy who’s very social.” Now I don’t know who was talking to this guy, but socializing can also be evaluated as being hammered. I enjoy meeting people and don’t put up a lot of blockades when I speak. I listen well (even drunk) and I engage. I’m not perfect, but I’m not a bump on the log. Many people like to talk to people they know. That’s not fun.
• Having Fun – When I go on vacation, I go to have fun and not sleep in a hotel room. I stay out as late as possible and experience as much as I can. This is life.

• Paying For Having Fun – The simple formula for having fun is 1 day of recovery for every day of fun. 3 days of having fun requires 3 days of recovery. This is my 3rd day. The last 2 were not fun (I did bowl a 269 yesterday somehow in a league). When you aren’t feeling 100% and have to work, you should never try to make any important decisions and wait to recover.

What I take from the trip is that there are awesome people on this planet. They know what a good time is and they don’t take life too seriously. Don’t work to make money that doesn’t get spent. Work to live life. I did exactly that this past weekend.