Why You Should Vacation In Boca Raton, But Only If You Are A Certain Type Of Person

A number of years ago, I made the quite unexpected decision to move to Boca Raton, Florida. I wasn’t doing much at the time, and there was a certain person in my life whose company was well worth following to the beach. During our nine months in Boca, she and I stumbled upon a Big Life Truth, the kind of philosophical certainty that can serve as a guidepost for a lifetime. That revelation was this: Southeast Florida is perhaps the most deeply insane region in this country. The madnesses which populate the narrow strip of civilization running from West Palm Beach to Key West are of a wild variety and sun-baked intensity unparalleled in my experience. It was my time in Boca that inspired my theory of Winter the Assassin and Warm Weather Insanity, as detailed here.

Upon returning to the Midwest, we were initially relieved to have stepped back to a much more understated level of insanity, but after a few years, the bizarre lure of Boca called us back, if only for vacation-length periods of time. In January, we embarked on our fourth Boca Raton winter pilgrimage in the last four years (the tropical location from which I watched the NFL Playoff Game Which Shall Not Be Named). It takes a certain kind of person to enjoy the unusual mix of peaceful beaches, insane residents, absurd wealth, and great eating, and if you are that person, you should definitely go and enjoy these, the ingredients that make up the mad mad sandbox of Southeast Florida:

1. The People.
Boca Raton is a people-watcher’s Garden of Eden. If you take pleasure from observing the constant comedy that is the General Public, then you’ll love watching the behavior of and interaction between the three major population demographics:

The Miserably Retired:
Using only your facial muscles, stretch the corners of your mouth down and outwards in an expression of displeasure. Maintain this expression for thirty years, and you will have achieved the basic facial appearance of the multitude of retired New Yorkers who populate Boca Raton. Now add a thick east coast accent, a mid-level Mercedes sedan, a half-million dollar condo, and an inexplicable sense of deep discontent with every aspect of the universe, and you are ready to move to Boca! Go to nice restaurants, split a hamburger, and tip miserably! Walk on the beach in dress socks and sandals, bemoaning the heat! Dispose of the words “thank you” and the emotion gratitude! And, most importantly, when the idealistic manager of your local Whole Foods decides to not only put out a complaints box but to post the complaints and his responses to them on a bulletin board, make sure that there is never a square inch of that board showing! Plaster that sucker with angrily scribbled rants such as, no kidding, “All of your food is TOO SPICY!!! I can’t eat anything, it’s TOO HOT!!! And your prices are going up too fast! Five months ago soup was $3.89 and now it’s $4.09!!!”

The Beautiful People
This one is easy. If you’re a man, make more money than God, usually in investment banking. Be single at age forty-five, drive a car costing slightly less than the gross national product of Ecuador, wear a watch that costs five figures, spend hundreds on expensive tequila, tan a lot, and ignore the ugly people. If you’re a woman, cut and color, lipo, implant silicone, get a nose job and face lift, tan tan tan, shop exclusively at Bebe, be staggeringly dumb but with an attitude, and sleep with the aforementioned men so they can fund your self-mannequinization. Also ignore the ugly people.

The Immigrants
Come to America, get a job in the service industry, make twenty times what you made in your home country, and get abused by the Miserably Retired and ignored by the Beautiful People. The only rational reaction to this, of course, is not to give a rip shit about the quality of your work (which is sometimes great and sometimes hilariously neglectful), because it’s going to be derided or ignored pretty much no matter what you do, so you’d better develop some thick skin.

Take these three demographics, add them liberally to a Boca Raton beach, restaurant, or grocery store, shake well, and there are endless moments of entertainment, if you like that sort of thing.

2. Driving.
I don’t know why there are so many roller coaster-filled theme parks in Florida, because the highways are much more exciting. On our recent visit, we were on I-95 for no more than ninety seconds before a brand new Ferrari F360 Sypder passed us going at least 105. Because the Miserably Retired are going fifty-seven in the carpool lane (and randomly dispersed throughout of the other lanes), he was going 105 in an insane, gas-brake-gas, zig-zag manner, tailgating and swearing a lot. This is completely normal. The F360 Spyder could just as easily have been a beat-up Chevy pickup filled with landscaping equipment, although the Chevy’s exhaust tends to contain a bit more oil smoke.

If you do survive the highways, be very careful navigating the side streets, because they are designed, casino-like, to trap innocent drivers who can’t tell the difference between Southwest 2nd Terrace, Southwest 2nd Street, and Southwest 2nd Court, all of which are within five hundred yards of each other. And two of them intersect. And one of them is not a court, despite its name. You must therefore drive offensively and stay on the main roads, which is a nice challenge, if you like that sort of thing.

3. The Opulence.
Boca Raton is absolutely dripping with ostentatiously spent cash. The city itself is immaculately manicured, with palm trees and parks and cool South Florida architecture everywhere you go:

The people, as you might have gathered, are pretty well off, and they expect to be treated as such. There is valet parking everywhere. Everywhere: At the grocery store. At the movie theatre. And, of course, at the upscale outdoor mall, Mizner Park, where the valets send the boring Cadillacs and BMWs off to the parking garage but leave three or four especially shiny cars sitting by the valet stand for everyone to see. On this latest trip, we drove by the Mizner valet stand at about 2:00 on a Thursday afternoon and saw, lined up neatly bumper-to-bumper, an Aston Martin V12 Vanquish, a Lamborghini Diablo, and Ferrari 575 Maranello. This is a mall, a car show, a fashion show, and a dog-and-pony show. This is also completely normal, and extremely entertaining, if you like that sort of thing.

4. The Eating
The aged and the wealthy sure don’t do a lot of home cooking, so the concentration and variety of restaurants in Boca Raton is pretty well off the charts. Food from all around the world is available at an excellent variety of unique, non-chain eateries. I recommend Max’s Grille in Mizner Park, not just because I worked there, but also because the food is nothing short of ridiculous. Ask for a table outside by the fountain, enjoy the warm night air and bustle of the dinner hour in Mizner, and order the Pistachio-Crusted Grouper with Wasabi Smashed Sweet Potatoes. If, of course, you like that sort of thing.

5. The Sun and Sand.
There is something to be said for walking outside in mid-January and not having to brace yourself for the soul-tearing wind, and Boca Raton is a good place to go if you need a break from winter. As advertised, the sun shines constantly, the breezes are balmy, the humidity is low, and the temperature – average January high: seventy-six degrees – is perfect (Well, perfect in the winter. Summer is slightly cooler than fire.) The beaches are just what you’d expect from South Florida: sky-blue water, soft sand, fluttering palms, and an assortment of the aforementioned General Public. Add a spectacular ocean-side jogging trail and some beachfront restaurants, and Boca Raton on the Atlantic is a delightful and relaxing place to sit on a beach chair and read a good book. If you don’t like that sort of thing, then why are you still reading?


As you might have possibly gathered, the Boca Raton beach vacation is not for everyone. Personally, I love it, and I can’t wait to go back next year. The weather is utterly relaxing, the food is unbelievable, the beaches are splendid, and the populace is guaranteed to provide a healthy dose of human comedy. I also love a quiet, nature-filled vacation on a regular basis, but variety is an important thing. So go, you food lovers, you people watchers, you January tanners, go to Boca Raton and enjoy the beautiful insanity of South Florida.