My latest trip landed me in Palm Beach, one of the wealthiest places in America. I stayed across the bridge in West Palm because I wasn’t paying $1,100 a night for the Breakers, but Palm Beach is one of those places where crossing a bridge feels like entering a different world.
My trip began at the Waldorf Astoria in Orlando because I wanted to experience what luxury hospitality actually looks like. My first impression wasn’t exactly inspiring. I arrived at 3:30pm and check in is 4pm. The concierge told me he had to check to see if a room was available.

If I was told to wait the 30 minutes it would have been a bad start. I can’t explain exactly why I would expect the room to be ready 30 minute early. Am I alone here?
Next, and I know this one, welcome to tipping nation. I paid $60 for valet and tipped the guy another $5 to park my POS Nissan Rogue. Nothing is wrong. $1 is cheap. Would I tip $5 if they are parking my Bentley? $50? I would have done self park but that was $40 so why not?
The room was nice, but not dramatically nicer than plenty of other hotels I’ve stayed in. One thing I appreciated was being able to walk over to the golf course at 4 PM with no tee time, rent clubs, and play a round for $150 on a completely empty course. I’m not sure they ever witnessed a golfer finish in 90 minutes.
Then I went to take a shower and only got lukewarm water. I’m not sure if this is ask for another room worthy.
Not luxury.
Later, I spent some time by the pool and came back to find my towels replaced and the television set to jazz music. I hadn’t been gone more than two hours and they were snooping around my shit. The only other place I’ve experienced that level of attentiveness was in Venice, where hotel staff seemed personally invested in making sure your room was perfect every time you left. Maybe that’s what makes the tip as there was a QR code to tip which I’ve never seen before.

After an overpriced dinner at the bar, I called it a night. The highlight of the stay was actually brunch the next morning. For $45, the service was excellent and the food quality was outstanding. Looking around the room, I couldn’t help but think they were doing their part to keep an already well-fed clientele even better fed. I had 2 chocolate chip cookies and a glazed donut before 8am and would have ate more if I didn’t feel like a fat ass.
From Orlando, I drove south and caught up with an old friend in Delray Beach. He showed me a country club community that costs roughly $48,000 per year to belong to. Everything was beautiful. Everything was perfectly maintained. Everything was filled with retirees.
I can absolutely see the appeal at seventy. I was the youngest person in the restaurant by decades. It felt odd.
Afterward, I headed to West Palm Beach and checked into a much more ordinary Hilton that at least managed to provide hot water. A country music festival was taking place nearby, so cowboy boots were everywhere. The atmosphere felt relaxed, the weather was perfect, and the people were noticeably more attractive than what I’m accustomed to seeing around Philadelphia. West Palm struck me as a place with a lot going for it.

The next morning, I went for a run along the beach in Palm Beach. The scenery was beautiful. The weather was hot. The ocean was bright blue. I imagine the novelty eventually wears off if you live there, but for a few days, I thoroughly enjoyed it.
Later, I met up with an old friend from high school and his parents. Larry and Susan are some of the kindest people I’ve met. There’s something uniquely rewarding about talking about life with people who’ve known you since childhood. You’re now a mature adult, and they’re reflecting on a life largely lived, which gives those conversations a depth that’s hard to replicate.
We grabbed coffee at the Breakers and had lunch at the Colony Hotel, both of which lived up to their reputations. The Breakers is one of those places that’s worth experiencing at least once. The Colony had excellent food. After lunch, we wandered from bar to bar and did some people watching.

Palm Beach has a unique quality to it. You have absolutely no idea whether the person walking past you is worth one million dollars or one billion dollars. I saw five Rolls-Royces during a short walk between stops, which tells you something about the neighborhood. I couldn’t imagine jumping out of a Ferrari in front of my house in Northern Liberties.
At one point, Larry was looking for a suit, so we visited Zegna, Brioni, and Brunello Cucinelli. Larry taught me that if you want to sound like you know what you’re talking about, you ask whether the pants are lined.
I considered whether I wanted to buy a $1,000 T-shirt. Then I remembered I’d probably spill something on it, rip it, and spend the next six months being angry about it.
Meanwhile, my friend Dave was handed a complimentary glass of Yamazaki whiskey that normally costs around $75. That’s the sort of place Palm Beach is. The entire area is spotless. There are no visible signs of disorder. People are pleasant. The service is exceptional. If I make another $10 million, I’m moving in. That seems to be about the minimum requirement for not feeling poor.

What I find most interesting about places like Palm Beach isn’t the luxury itself. It’s the opportunity to observe how wealth operates.
Walking through stores filled with $6,000 hand-stitched suits and $1,000 T-shirts didn’t make me feel jealous. It made me curious. I wouldn’t wear most of that fashion even if it were free. I imagine people have so much money that they need to spend it on something and fashion is one of the best way to promote yourself. These designs look ridiculous (in my opinion) but clearly I know nothing.
Trips like this remind me that there are entire worlds operating at levels most people never see. Exposure matters. Every time you spend time around successful people and successful environments, your understanding expands a little further.
Even feeling out of place has value. The first time you walk into an environment like that, you’re an outsider. I guarantee all those store clerks knew I wasn’t buying shit and was some schlub.
Wealth and success generally travel together, and I aspire to both. Not because I want the $1,000 T-shirt, but because I want the freedom, opportunities, and perspective that come with reaching a higher level. Every trip like this leaves me with new ideas, higher standards, and how to get there. Another trip in the books.
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