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Orlando, USA · February 2025
Orlando via Brightline
This time I took the train. Brightline runs from Miami to Orlando in about three and a half hours, which is roughly the same as driving but without the I-95 to Turnpike to I-4 gauntlet that makes every Orlando drive feel like an endurance test. The...
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This time I took the train. Brightline runs from Miami to Orlando in about three and a half hours, which is roughly the same as driving but without the I-95 to Turnpike to I-4 gauntlet that makes every Orlando drive feel like an endurance test. The train leaves from MiamiCentral downtown and arrives at Orlando's new station near the airport. The seats are wide, the Wi-Fi works, and there's a cafe car with decent coffee and surprisingly good snacks. I worked for most of the ride, which is the whole point. Three and a half hours of uninterrupted laptop time versus three and a half hours of white-knuckle Florida highway driving. Not a hard decision.
The morning departure was 7 AM, which meant I was at MiamiCentral by 6:30. The station is downtown near the government center and at that hour it's mostly commuters and a few conference types with lanyards already around their necks. The Select cabin (their business class) has wider seats, free coffee, and a quiet car energy even though there's no designated quiet car. Everyone is working or sleeping. Nobody is talking on speakerphone, which alone is worth the upgrade.
One night at the DoubleTree by Hilton Orlando Airport. The DoubleTree is near the Brightline station, which made the logistics simple. It's a DoubleTree. You know what you're getting: the warm cookie at check-in (which I ate immediately and have never not eaten immediately at any DoubleTree ever), a clean room, a bed that works. The hotel is not the story. The conference is the story, and the conference was one day.
I spoke in the morning to a room that was more engaged than I expected for a smaller event. The questions ran long, which is the best indicator. One woman in the audience asked something about building a personal brand when you work inside a large company and don't want to seem like you're competing with your employer. It's a question I hear a lot and there's no clean answer, which I told her, and then I gave her the messy answer, which involves having a direct conversation with your boss before you post anything and making sure your content helps the company more than it helps you. She nodded like that was the answer she was hoping not to hear. Honest answers are like that sometimes.
After my session I stayed for two more panels and then had lunch with the organizers at a restaurant near the hotel. Standard conference lunch: salads, sandwiches, a conversation that starts professional and ends personal by the time the check comes. One of the organizers had been following my work for a couple of years and we talked about the gap between what people see online and what the actual day-to-day looks like. She said something I liked: "Everyone shows the keynote. Nobody shows the four hours of prep the night before." I told her that's exactly exactly what people should be making. She said she knew. She just hadn't started yet. The gap between knowing and doing. My favorite subject. I told her the only thing standing between her and the first piece of content is the willingness to be mediocre in public for a few months. Nobody's first post is good. The people with big audiences started with small audiences and worse content. She pulled out her phone and took a note. That felt like progress.
The DoubleTree lobby had a small bar area and I sat there for an hour after the conference waiting for my Brightline departure, answering emails and eating a second cookie that the front desk offered when I walked past. Two cookies in one stay. That's a personal record. The bartender asked if I was there for the conference and we ended up talking about Orlando's growth and how the area around the airport has changed over the past five years. He'd lived in Orlando his whole life and had opinions about every neighborhood. He said the Mills 50 area on the east side was where the interesting food was happening. The same thing the JW bartender Marcus had told me last year. Two bartenders, same recommendation. I still haven't been. It's on the list.
The Brightline station in Orlando is new and still has that just-opened feeling where everything is clean and the signage is clear and nobody working there looks tired yet. I grabbed a coffee and a sandwich from the station cafe (the sandwich was better than airport food, which is a low bar but Brightline clears it) and settled into my seat for the return.
The ride back to Miami was the reverse of the morning: laptop open, coffee cooling, Florida sliding past the window. The landscape between Orlando and Miami is almost entirely flat and green with occasional pockets of development that appear and disappear like islands. There's a stretch south of Cocoa where the train runs alongside the Indian River and the water is visible through the trees, which is the most scenic 15 minutes of the entire route. I closed my laptop for that stretch and just watched. The water was flat and silver and a heron was standing in the shallows doing absolutely nothing, which seemed like a reasonable approach to a Wednesday afternoon.
I got back to MiamiCentral around 7 PM, took an Uber home, and was on the couch by 8. G had made dinner (pasta, simple, good) and asked how the conference was. I told her about the personal brand question and she said "that's the question everyone's afraid to ask their boss" which was a better summary than anything I'd said on stage.
The Brightline changes the math on Orlando trips. No airport security, no rental car, no parking garage, no gas. You walk on, you sit down, you work, you arrive. For a one-day conference, the train is the answer.
Travel Tips
Best TimeMarch to May
MoneyCredit cards are widely accepted everywhere in Orlando, but it's always a good idea to have some cash on hand for smaller purchases or tips.
LanguageEnglish is the primary language spoken in Orlando, but you'll hear a variety of languages due to the city's international appeal.
What to Pack
A stylish, reusable water bottleA portable power bank for the train and long days outComfortable yet chic walking shoesA lightweight rain jacket or compact umbrellaA small backpack or crossbody bagNoise-canceling headphones for the Brightline journeyA good book or downloaded playlist for the train rideA versatile scarf or pashmina
Tips We Wish We Knew
Upgrade to Premium on Brightline
Book Brightline in Advance
Explore Beyond the Theme Parks
Rideshare from the Station
Pack for the Train Ride
Trip Cost Breakdown
Business class, upgraded rooms, fine dining, and private transfers.
Est. Total Per Person$1,100
2 Days · Per Day$550
Hotels$500
Food & Drink$300
Local Transport$300
Estimates per person based on our experience. Prices may vary by season and availability.
Day by Day
7:00 AM
GoBrightline train from Miami to Orlando
11:00 AM
GoArrive in Orlando and head to the hotel
12:00 PM
StayCheck in at the DoubleTree by Hilton Orlando Airport
1:00 PM
EatLunch near the hotel
3:00 PM
DoFinal prep for the conference talk
7:00 PM
EatDinner at the hotel

