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Orlando, USA · January 2024
Orlando in January
Five nights at the Wyndham Orlando Resort International Drive in mid-January. Conference. The Wyndham is a conference hotel and it does conference hotel things without pretending to be anything else. Large lobby, pool with a waterslide that nobody...
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Five nights at the Wyndham Orlando Resort International Drive in mid-January. Conference. The Wyndham is a conference hotel and it does conference hotel things without pretending to be anything else. Large lobby, pool with a waterslide that nobody over 12 uses, rooms that are clean and forgettable. I-Drive is Orlando's tourist corridor, and walking it at night feels like being inside a pinball machine: chain restaurants, outlet malls, go-kart tracks, and a SkyWheel that lights up in colors that would be illegal in most European cities.
One evening after the sessions I walked I-Drive for about 40 minutes just to stretch my legs. Passed a dinner theater, a Ripley's Believe It or Not, three different buffets, and a store that sold only hot sauce. The hot sauce store was the most interesting thing on the strip. The guy behind the counter had me sample something called "Stupid Hot" and my eyes watered for ten minutes. I bought a bottle. It's still in our fridge. G uses it on eggs. I use it on nothing because I've learned my lesson.
The conference itself was productive. Spoke on a panel the second morning to a room that was about three-quarters full, which for a 9 AM slot at a conference in Orlando is a win. The other panelists were sharp. One of them, a woman running a content agency out of Chicago, said something during the Q&A about how most brands are "producing content for algorithms and wondering why humans don't care," which stuck with me long after the session ended. We grabbed coffee after and talked for an hour. Those accidental connections are the actual product of conferences. The scheduled stuff is the wrapper.
The hallway conversations were good this trip. I met a founder building something in the creator space who'd been listening to my stuff for a couple years. We sat in the hotel lobby for two hours on the third night talking about monetization and audience building and the gap between what people teach and what actually works. He was further along than he realized. I told him that. Sometimes the most useful thing you can say to someone is "you're closer than you think." We stayed in touch after.
January in Orlando also means the parks are at their emptiest, which I noted but didn't act on because I was working. But if you're ever going to do Disney or Universal, January and early February are the window.
The food on I-Drive is mostly chains, but I found a Colombian place on a side street near the convention center that did bandeja paisa with a fried egg on top and rice cooked in coconut milk. The portions were enormous and the bill was $14. I went back twice. Never got the name. It had a yellow awning and a parking lot that fit four cars. On the last night, a group from the conference went to Nile Ethiopian Restaurant on International Drive, which was a step up from the Applebees-and-TGI-Friday's landscape around it. About eight of us, most of whom had met for the first time that week. We ate with our hands, shared platters of injera and doro wot and a lamb tibs that was spicier than anyone expected. The table conversation started with business and ended up somewhere around "what would you be doing if you weren't doing this," which is the question that comes out at the end of a long conference when everyone's guard is down and the wine is working. The answers were surprisingly honest. A graphic designer. A fishing guide. A teacher. Nobody said "exactly what I'm doing now," which tells you something about the people who go to conferences. They're all reaching for something slightly different than what they have. The bill was $120 split eight ways, which for a dinner that turned a table of strangers into something closer to friends felt like a steal.
The Wyndham pool became my decompression spot between sessions. I'd grab a coffee from the lobby, find a lounge chair away from the waterslide zone, and just sit for 30 minutes with no phone and no agenda. Conference days are nonstop human interaction and my brain needs gaps. The pool provided them.
Orlando in January is 70 degrees and sunny, which after living in Miami doesn't feel special anymore, but I remember how it felt when I was flying in from Toronto in January and stepping off the plane into warmth felt like cheating. Now it just feels like Tuesday. One afternoon between sessions I sat by the pool and watched a family from somewhere cold (Minnesota plates on their rental car) react to the water like they'd discovered a new element. The kids went in fully clothed. The dad stood at the edge testing with one toe for about five minutes. The mom was already in. Moms always figure it out first.
I called G from the pool one evening and she asked how the conference was going and I told her about the Chicago content agency woman and the creator space founder and the Ethiopian restaurant and the hot sauce. She asked if I'd gone to any parks. I said no. She said "you've been to Orlando four times and you've never been to a park." She's right. I've been to Orlando for conferences and I've seen the inside of convention centers and hotel lobbies and I-Drive at night and I have never once ridden a roller coaster or met a character in a costume. This might say something about me. I'm not sure what.
The flight home was unremarkable, which is the best kind of flight. Aisle seat. Direct to Miami. Landed, drove home, showed G the hot sauce bottle. She used it the next morning. I watched from a safe distance.
Travel Tips
Best TimeOctober to April
MoneyCredit and debit cards are widely accepted, but it's always a good idea to have some cash on hand for smaller purchases and tips.
LanguageEnglish is the primary language, but you'll hear Spanish spoken frequently as well.
What to Pack
A packable rain jacketComfortable walking shoesA light sweater or fleeceA pair of shorts for warmer afternoonsSunglasses and sunscreenA reusable water bottleA portable phone charger
Tips We Wish We Knew
Book Dining in Advance
Layer Up for Parks
Explore Beyond Theme Parks
Check for Refurbishments
Trip Cost Breakdown
Business class, upgraded rooms, fine dining, and private transfers.
Est. Total Per Person$3,720
6 Days · Per Day$620
Hotels$2,000
Food & Drink$900
Activities$150
Local Transport$670
Estimates per person based on our experience. Prices may vary by season and availability.
Day by Day
3:00 PM
StayCheck into the Wyndham Orlando Resort
7:00 PM
SeeWalked down International Drive to get a feel for the area
8:30 PM
EatGrabbed a quick dinner at a chain restaurant


