Sarasota is famous for its extravagantly beautiful homes, from the ornate mansion John Ringling built in the 1920s to such modern architectural marvels as the two (count them, two) Gulf-front homes, both designed by Sarasota’s Guy Peterson, that just made a national list of the 10 Coolest Beach Homes in America. We regularly feature homes like that—in fact, one of those beach homes, a $15 million Sanderling property, was our June “Home of the Month”—and we’re always talking to architects, designers and other building professionals in search of the next big sensation.

But I have to confess that the homes we love most are often places that we happen to stumble upon and that evoke an instant emotional connection. That’s what happened when we were planning this Home & Garden annual. Our art director, Gigi Ortwein, was cruising off Jewfish Key, a 39-acre island east of Longboat that’s only accessible by boat. In the golden light of early evening, she glimpsed an idyllic scene. Two little girls were playing on swings beneath the wide, wooden porch of a house surrounded by Australian pines and palm trees and overlooking a sliver of beach. As she watched, the children tumbled off the swings, and, shrieking with laughter, disappeared into the woods. She turned to a friend and said, “We have to write about this place.”

That’s almost exactly how Steve Ellis and his family discovered the site that was to become their vacation home. A lifelong sailor and boater, Ellis anchored off Jewfish Key a few years ago so he and his wife and their one-year-old daughter could play on the sandbar just offshore. As they splashed in the water, he looked up and saw a “For Sale” sign among the pines. Ellis, who is a partner in a green building company, had an epiphany: “In just 40 minutes, we could travel by boat from our Sarasota house and be in another world.”

In this issue, you’ll share a weekend with the Ellises at their island getaway, where simplicity, intimacy and comfort rule. His aim in designing the house was as simple as it was successful: to recall “those nights on a sailboat when you look up and see the stars, feel the wind, and know exactly where you are on this earth.”

If you, like me, were a childhood fan of the film The Swiss Family Robinson, in which an impossibly photogenic family lived in the most splendid treehouse imaginable, you’ll fall in love with the Ellis home and another home in this issue, a Casey Key guesthouse perched in a coastal oak hammock. This striking modern structure has collected a number of prestigious awards and appeared in national shelter magazines, but like the Jewfish Key house, it’s designed in harmony with the land and for the comfort of its lucky guests.

You’ll also visit one of Sarasota’s most beloved neighborhoods, in Robert Plunket’s tour of the tree-shaded streets around the Ringling Museum, where he finds an eclectic cast of characters and some of the most interesting houses in town. And be sure to savor J.B. McCourtney’s photographic studies of the tropical plants in his garden, which he says are an homage to the home’s former owner and first gardener, the late, legendary designer Ben Baldwin.