The Anti-Wanderlust of Wintertime New York

There is a habit of New Yorkers to head South for the winter once they’ve reached a certain age or level of financial security. I can understand why but will fight to stay north for the winter as long as I can.

The deep chill of a January and February in New York can be no fun. The outdoors is windblown and desolate, and the normal stroll through the city that is normally a joy is an appointment with wincing pain. The chill combined with the dry air of the indoor heat stresses and fractures the skin, our eyes tear with windy cold, and we fumble for our gloves and try to find the way to both be agile of hand and not feel frostbitten.

But give me the most frozen winter on record and it will still be preferable to the constantly warmer climate of regions south. I can say this with certainty as I’ve had to go to Florida twice in the past three weeks for work and don’t wish to live in a perpetual spring and summer all year.

My first trip to the Fort Lauderdale area earlier in January was a suitable introduction to the tourist-fueled aquamarine madness of South Florida. Just because your company sends you someplace nice for work doesn’t mean that the real word stops, and it’s hard to enjoy the seaside camaraderie when you know a thousand emails are piling up on your laptop.

One of the more interesting parts of the trip was talking to the Uber drivers that ferried me about. In one evening I met a woman from Costa Rica who was an animal rights activist and got caught up in some controversy in her home country around money she raised for abused animals. Later on that night I had a driver whose full-time job was inspecting airplanes that were manufactured; he had been burned in a recent divorce settlement but was working his way back to fiscal and emotional health and had no problem telling a perfect stranger that (well, Uber passengers aren’t perfect strangers – the drivers arrive knowing your first name and have the right to charge your credit card; this may count as intimacy in this day and age).

My second trip to Florida was to attend a financial conference, the biggest of its kind for the investing niche it represents. It was so popular that I could not get a room at the hotel where the conference was held, and instead found shelter a few minutes’ drive away at the Margaritaville of Hollywood Florida.

As it sounds the Margaritaville is a hotel chain based on Jimmy Buffet’s tropical music. And despite this it’s actually a nice place. The room I had was nice with a balcony that had an ocean view. When I arrived, I thought the woman ahead of me at the check-in desk was wearing a pair of beige pants that made her look crudely exposed. But I was mistaken: my fellow hotel guest was speaking to the hotel clerk wearing nothing below the waist except a flimsy G-string bikini bottom and a pair of flip flops. This is what Floridians refer to as “business casual.”

Again, it was the cab drivers that wind up giving you a better flavor for the place. On my final day in Florida, I got to speak with a driver who had moved to Florida from New Jersey in 1973 (you meet very few native-born Floridians in Florida) and had seen it change tremendously. He liked it when it was less populated and he was younger. He had the easygoing manner of someone who had escaped the rat race years ago and could enjoy whatever life threw at him. He was a moderate liberal Yankee who was at ease with the easygoing ways of South Florida and could drink all afternoon with more right-wing friends and still go home friends. He maneuvered around the traffic islands and stoplights with an ease that escapes many of the ride-share drivers of today’s generation. It was a good way to begin my final day in the Sunshine State.

As the conference wound down, people were finishing up their business and making arrangements to get out of town. I managed to book an earlier flight and quickly caught a cab to the airport.

It was 75 degrees when I flew out of Fort Lauderdale and 39 degrees when I landed in New York. It was a strong slap in the face of cold air, but it felt like home.