Admit it—you’re intrigued. Sarasota, this place that you’ve stumbled upon, seems like a real find. It might be nice to have a place here. Now that you have the time and money to get out of New Jersey—or Illinois, or Ohio, or Connecticut—for the winter. And then you could eventually retire here. . .

But what would it be like, living here, month after month? Is there enough to do, other than go to the beach? Who would you make friends with? Would the “culture” seem a little second-rate after what you’re used to in Chicago and New York? Can you even afford it?

And most of all—you certainly don’t want to turn into an old retired person living in a condo in Fort Lauderdale, Clearwater, Boynton Beach, Sebring or Kissimmee. How is Sarasota different? You need somebody who really knows the place. And that’s where I come in. Let’s have a drink at the Ritz and I’ll fill you in on everything you have to know about life in Sarasota.

 

What makes Sarasota better than all the other towns in Florida?

Three things. First, the beach. Siesta Key Beach is now recognized as the best beach in the country (read more by clicking here), but that’s only part of the story. Locals find their own favorite, and the variety is enormous—Coquina, Caspersen, Lido, and my own personal favorite, Beer Can Island, which is officially located in Manatee County but close enough to call our own. With 35 miles of white sand beaches, Sarasota has something no other town in the country can offer.

Second, the scale. Sarasota is the perfect size. Everything is 10 or 15 minutes away. Downtown, the malls, the beach, the golf coursel—even the airport. You’re not going to spend hours in traffic. Yes, the Tamiami Trail—aka U.S. 41—can get a little crowded during the season, but it’s nothing compared to the endless six-lane roads of Naples or the urban sprawl of Miami and Fort Lauderdale or the bumper-to-bumper freeways of Orlando.

Third, the sense of history and community. Sarasota is a real town with a fascinating past: the circus, the artists’ colony of the 1950s and ’60s, the Sarasota School of Architecture. And it’s been lucky to have a great writer describe it—mystery novelist John D. MacDonald, who defined its moral code and probed what lurks beneath the beautiful surface. Today’s boisterous arts scene continues this tradition and provides a glue that other towns in Florida just don’t have.

 

 

What are my housing options?

You’ve probably figured out a lot of this already, as poking around the real estate market is a favorite preoccupation of visitors. But here’s a quick guide to how much buys what.

Under $200,000: a nice condo or small house on the mainland in a good neighborhood that will feel more suburban than beachy.

Up to $500,000: A great price point these days. You can get a brand-new four-bedroom pool home in a fancy gated golf course community, a two-bedroom luxury condo in a downtown high-rise, or a nice if not too elaborate place on one of the keys.

$1,000,000: The sky’s the limit. A beachfront condo on Longboat, a big house on Siesta (maybe not on the water), a palace-like mansion in a gated community. Sarasota specializes in dream houses, and at the moment you have your pick.

 

What will I do with my time? What will my days be like?

You’ll get up and have breakfast, hopefully in your pool cage, a horrible-sounding phrase meaning the screened enclosure surrounding your swimming pool. If you’re of snowbird age, you will probably read the newspaper. It’s pretty good, as are most of Sarasota’s media outlets. Soon you’ll be engrossed in the human comedy that is life in Sarasota these days—the parking debacle, the saga of attorney/power broker David Band and his family, not letting the homeless sit down in the parks, etc.

Budget for sunblock, as you will be outdoors a lot. Most people use their move here to improve the physical aspects of their lives, and Sarasotans are great walkers, runners, kayakers, cyclists, paddleboarders, rowers, bird watchers. The opportunities are endless; and don’t forget, it’s year-round.

The long sunny afternoons are perfect for antique and thrift shopping, going to the movies, and naps. You’ll go out to eat a lot; many of those condo kitchens are used strictly as pantries, not places to actually cook. Part of the fun of living in Sarasota is trying the new restaurants.

And in the evening you’ll discover that all this arts capital stuff is not hype. The arts are one of the town’s biggest businesses, and you know what that means—not just performances and exhibitions but lots of feuds and egos and controversies to follow and take sides on. You’ll soon discover your niche as an audience member, be it the musicals at the Players, the BluesFest, the Friday Art Walk. The first place to dip your toe is the Van Wezel, where every season you’ll find out what happened to the stars of 20 years ago—they tour Florida every winter. This season we have Dolly Parton, k.d. lang, Neil Sedaka and Frankie Valli, just to name a few.

 

 

How will I meet people?

I have never in my life had to “meet people.” I always relied on school and then work to provide me with a steady stream of friends. Many snowbirds find themselves in this same position, and it can be daunting.

The traditional answer to this question is to volunteer. I’ve always found this a little annoying. Volunteer at what? With whom? The first time I volunteered I found myself making fund-raising phone calls from a list I was handed. Not my idea of fun. And I made more enemies than friends.

They say to pick organizations that fit your interests, but even that is a little vague. I’ve found the most foolproof volunteer venue is politics. You will find like-minded people who share your values, and with any luck you’ll be thrust right into the middle of the action. Local politics, national politics, they’re both good. But local politics will be a crash course in how the town works.

Keep your eyes open for “only in Sarasota” experiences. Southeastern Guide Dogs needs people to train and socialize puppies so they can work with the handicapped. And the arts provide a never-ending stream of hands-on activities. Don’t just think in terms of ushering, though that’s fun as long as you’re not dyslexic and have comfortable shoes. I was a super at the opera in a production of La Traviata—I played a waiter—and watching an opera come together and then actually performing in it was a once-in-a-lifetime experience.

 

What are the people like?

In general the town is much more liberal than most wealthy Florida enclaves. Planned Parenthood is a big deal, and Sarasota was a pioneer in AIDS fund raising. There are a surprising number of women running things—publishing, real estate, medicine, the arts, philanthropy.

It is also more intellectual than you might suspect. It has always drawn thinkers. When you take a look at Sarasotans who have changed the world, you find a diverse list of overachieving intellectuals with unusual passions—Eugenie Clark (she pioneered shark research), John D. MacDonald (he invented the Florida mystery novel), Paul Rudolph (famous Modernist architect), Chick Austin (early champion of modern art and as director of the Ringling Museum laid the foundation for Sarasota as an arts town), Pee-wee Herman (comic genius and product of the local arts scene). Today the tradition continues with novelist Stephen King, the ultimate Sarasota snowbird. He divides his time between Maine and Casey Key.

But chances are you won’t find yourself living next door to an eccentric genius. Your neighbors will be a lot like you—late middle age, stylish but not flashy, sociable, glad to have access to all the town’s amenities, but more interested in their children and grandkids. And their children and grandkids will be interested in them. No one ever lost points with their relatives by buying a place in Florida.

Are there any drawbacks?

In a word, September. It’s worse than August. The heat continues and the town is cranky and half-empty. The threat of hurricanes hangs over everything. (Although I must point out that in the 30 years I’ve lived in Sarasota there has never been a serious hurricane here—knock wood. This year more people were killed by hurricanes in Vermont than in Florida.)

It isn’t all sweetness and light. Sarasota is a real town, with life in all its various dimensions. We have murders and crimes and Ponzi schemes. The 9/11 hijackers lived among us for a year. The murder of two British tourists here in April—one was from a snowbird family on Longboat—showed an ugly side of Sarasota, an unhappy mix of alcohol and racial tension. But as we keep telling ourselves, that could happen anywhere.

 

What do I do first?

Start going to the Farmers Market. It’s every Saturday morning downtown. You’ll find local produce, baked goods, jams and salsas, crafts, live music. Everybody goes, and the socializing is great.

Visit the Woman’s Exchange regularly. Not to exchange women, but to purchase high-quality used furniture, dishes, artwork for your new house or condo. It’s the Saks Fifth Avenue of secondhand stores.

Walk on the beach at sunset. Chances are you’ve already done this. It’s a thrill that never diminishes. Here the sun sets over the water, a rarity on the east coast. If you ever wonder, “Why did I move to this dump?” just go to the beach at sunset and you’ll remember why. An instant cure for Snowbird Remorse.

Adopt a dog. Sarasota is a great dog town. Most restaurants with outdoor seating welcome them. There is a doggie beach and several doggie parks. And if your snowbird status makes you nervous about hauling a pet back and forth, consider fostering a puppy or a kitten for a month or so.

 

If Sarasota is so great, why isn’t it more famous?

In a word, jealousy. The other towns spend millions touting their inferior wares, while Sarasota just sits back and lets people discover it. They out-shout and out-hustle us, and frankly that’s the way most of us want it. We’re above the fray—a shining city on the beach, rich with amenities, a vibrant intellectual life and some rock-bottom real estate prices, too.

Senior editor and novelist (My Search for Warren Harding, Love Junkie) Robert Plunket has written about Southwest Florida for The New York Times, Barron’s and other publications.

 

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