Island Lifestyles


TThe idea of living on an island draws upon images of fruity cocktails, hammocks swaying with the breeze and glorious sunsets ablaze with orange and red puffy clouds, the perfect finale to a peaceful day in paradise. Perhaps in today’s over scheduled, high-tech world, an island lifestyle is more coveted than ever. Islands have always captured our imaginations, a timeless theme in Literature and Film-from Robert Louis Stevenson’s masterwork “Treasure Island” to countless movies, including a 1948 classic called “On an Island with You” starring bathing beauty Esther Williams, a movie with local provenance. Although the story was set in the South Pacific, many of the film’s most spectacular exteriors were actually shot right here on the Gulf Coast on what was then an unspoiled, exotic paradise – Anna Maria Island – only 20 miles north of Sarasota.

In fact, Southwest Florida is home to a wide assortment of islands, all with their own distinctive personality. Anna Maria Island is the northern most jewel in a dazzling chain of island gems that hug the coastline. Beginning at the mouth of Tampa Bay, this gorgeous assortment of islands and keys stretch to the south, hugging the shores of Sarasota, winding their way down to Gasparilla Island and rustic but elegant, Boca Grande, then Sanibel and Captiva Islands and finally the little jewel, Marco Island at the southern tip of west Florida.

Anna Maria
Gulf front Anna Maria Island

Although exploring the islands from behind the wheel of a convertible would be a blissful way to spend the day, and probably the best way to experience the personalities of each island community, to experience the sheer natural beauty, along with some of the most spectacular waterfront real estate anywhere in Florida, why not park the convertible and board a boat?

Let the crystal clear waters of the Gulf of Mexico serve as your highway as you travel south from the casual community of Anna Maria Island to exclusive Longboat Key. This 11 mile long island was once a wilderness inhabited by the Caloosa Indians, then explored by Hernando DeSoto in the early 16th century, who paddled through the north pass with his guide via a “Longboat”. Five hundred years later, Longboat Key has become one of the premier resort communities in Florida, offering world-class golf courses, tennis facilities, deep water marinas, plenty of shopping and fine dining, all of it surrounded by grand estates and spectacular condominium developments.

Longboat Key Club Condo
Longboat Key Club Condo

South of Longboat Key, and just across the bridge from downtown Sarasota, you’ll find Lido Key, which is actually a small cluster of three tiny islands. Bird Key is the name of the island as well as the exclusive yacht club community that envelops it.  St. Armand’s Key is home to St. Armand’s Circle, with its posh shopping, exceptional dining, and exciting nightlife.  And Lido Key is the home of the world renowned Mote Marine Laboratory and the lovely Lido Shores enclave, a residential neighborhood, brimming with old Florida cottages mixed among extraordinary architectural masterpieces from the Sarasota School of Architecture.

Siesta Key Home
Siesta Key

Just south of Lido we find Siesta Key, the ultimate in Florida beach casual. While Gucci sandals may be the footwear of choice on St. Armand’s, on Siesta Key, it’s all about the flip-flops. As late as the 1940s, Siesta Key had less than 300 inhabitants, while today it hosts more than 100 times that many visitors every year. Despite its growing popularity over the past 70 some years, Siesta Key has managed to retain its quaintness and charm. This may be due in part to the lasting legacy of the island’s colony of world famous artists who, beginning in the mid 1950s, escaped the stress of the mainland to imagine and create on Siesta. In its heyday, Siesta Key’s artist colony was home to nearly 100 artists, including Impressionist Syd Solomon and Illustrator and Watercolorist Thorton Utz. Siesta Key remains a place that captures the imaginations of artists, or those possessing the soul of one.

Stunning Gulf-to-Bay estate  on Casey Key
Stunning Gulf-to-Bay estate
on Casey Key

Crossing the mouth of Little Sarasota Bay, we find Casey Key, home to some of the Gulf Coasts’ most exquisite properties. Organic yet refined, Casey Key is the ideal destination for those who value unspoiled natural beauty and privacy above all else. No high rises or street lights, Casey Key is a collection of charming old Florida style beach cottages and a few Mom and Pop run motels at one end of the spectrum, and at the other, estates so grand and magnificent they must be seen to be believed. Some of the island’s extraordinary Gulf-to-Bay estates offer the waters of the Gulf of Mexico in the front yard and peaceful bay views in the back. What could possibly be more delightful? A private island, we have some of those as well.

West Wind on Casey Key
West Wind on Casey Key

Heading south again, we find Gasparilla Island’s famed Boca Grande, just south of Casey Key. Quiet, gracious, and known for some of the best fishing in the world, Boca Grande is a different way of life. One that has attracted some of America’s oldest and most influential families who for generations have made this remote tropical paradise their second home.

Little Bokeelia Island
A private island oasis,
Little Bokeelia Island

Just below Boca Grande, a myriad of tiny islands sprinkle the waters of Pine Island Sound. In fact, anyone looking to purchase an island oasis should visit the exquisite private paradise featured on page 16, Little Bokeelia Island.

Island living on Florida’s Southwest coast is as good as it gets, so whatever your personal tastes may be, there is an island lifestyle for you. And if you want to keep your options open and enjoy a little taste of what each of them has to offer, they are all just a short drive, or an even shorter boat ride away, waiting for you to explore.




Coquina Beach
Located on the south of Anna Maria Island, it is one of the most beautiful beaches in Florida, soft white sand, crystal clear waters, no crowds, a snack bar and restrooms.

Shopping on the Circle
St. Armands Circle, located across the bridge from Downtown Sarasota, offers a wide variety of shops and restaurants.

Adventure Kayak Outfitters
Rentals and Adventure Tours of Mangrove Tunnels on Lido and Siesta Keys.

Reel Intense Inshore Charters
One of Southwest Florida’s best charter fishing companies located on Boca Grande.

Shelling on Sanibel Island
Renowned for it’s seashells, this beautiful island is one of the best beaches in Florida to find unusual seashells.