Snowbird Confidential

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.