Eight Florida isles, no two alike

On Siesta Key, a spectacular sunset can be even more special with a tropical cocktail in hand and one’s feet planted in the soft quartz sand. The beach rates high even with Dr. Beach. (Sarasota Convention and Visitors Bureau)

GULF ISLANDS, Fla. - If I were a brown pelican, flying high above the Gulf of Mexico near Sarasota, I imagine that I would see thin strips of land trimmed in white, surrounded by water as clear and blue as the cloudless sky above. However, I am not a bird. I am flightless, and as I drove across bridge after bridge to eight different islands in the chain, I found that though they all inhabit the same body of water, they are hardly identical octuplets.

Nor are these islands clones of the Florida Keys, the more popular and party-wise archipelago off the state's southern tip.

The Gulf Islands are arranged like steppingstones along the western coast of Florida. You can skip from one to the other - Anna Maria Island to Longboat Key, City Island, St. Armands Key, Siesta Key, Casey Key, Venice, and Manasota Key - with few interruptions. But as I ventured from one key to another, I couldn't help noticing that what I had left behind only faintly resembled what I had just arrived at. The structures, natural environments, amenities, mind-sets, and even sand compositions varied remarkably, creating islands with unique, identifiable characters.

They say that no two snowflakes or Baldwin brothers are alike; I'd add the Gulf Islands to that list.


Anna Maria Island

Low-key and all-natural

Anna Maria Island is Florida as a living diorama, with no chain hotels, a speed limit that never exceeds 35 m.p.h., and a building limit of three stories. It is also home to a genteel first lady.

"We are loath to go the route of Longboat Key, with condo high-rises," said Rhea Chiles, the wife of former Florida Gov. Lawton Chiles, whose family has owned property here since 1958. "The look of the place has been passed down from one generation to another. It's all of those words: quaint, neighborly, natural."

Chiles was the visionary behind the Studio at Gulf and Pine, a multi-use space that exhibits local artworks, including a painting of her own, and holds classes, such as the book club I was making her late for. So I left Chiles to her plot twists for the turns of a kayak.

Shawn Duytschaver, whose family opened the first gift shop on Anna Maria, owns Native Rentals, where he rents boats and preps guests before pushing them off to fend for themselves. He suggested that I paddle Robinson Preserve, a 400-acre mangrove and salt marsh reserve that opened in 2008 and is buffered from motorized traffic. (By comparison, around nearby Lido Key, kayakers must contend with the din of boats and cars, he said.)

At the put-in spot across the Intracoastal Waterway, Duytschaver handed me a laminated map and said I could probably make it to the bald eagle nest before sunset. He also warned me about the black "bugs" in the mangroves. They're not spiders, he said, but crabs. Underlying message: Don't freak out and abandon ship.

I found the small entryway to the preserve but got my left and right confused. Instead of kayaking in the wider bayou (to the right), I ended up in the narrow tunnel, where mangrove roots kicked out like chorus girls. In several areas, my paddle was wider than the channel. At one point, I was so wedged in, my only choices were stand up and pick up the boat or try an eight-point U-turn. Only the crabs know which option I took.

Abandoning the mangrove, I entered open water, where mullet were jumping so high and so close to my boat that I could feasibly have landed one with some clever maneuvering. I hadn't gotten far into my laissez-faire fishing when I spotted a bald eagle sitting stoically in a tree. Having reached my goal, I turned back, a much easier trip now that I was wise to the tangle of mangroves.

On the Gulf Islands, sunset is a momentous occasion. At the Sandbar Restaurant, on the beach on Anna Maria Island, waiters ask diners to guess the time of the sun drop. Those with the correct answer win a bottle of champagne.

The wait for a table exceeded the time left before sunset, so I watched the show from a dugout in the sand. At 6:58, a bell rang. Couples kissed and families snapped photos with the cranberry-streaked sky as a backdrop. I overheard a waiter consoling his customers about their losing time, trying to ease their disappointment with dessert.


Longboat Key

Exclusive, from gates to Gulf

I had been spoiled by Coquina Beach, the last strand on Anna Maria before you enter Longboat Key. From the road, you could see the Gulf without obstruction and reach it easily. Once on Longboat, the buildings and bushes grew higher, the water views became scarcer, and I turned into a persona non grata.

The island is dominated by gated resorts. The keeper at Longboat Key Club and Resort, a high-end property that resembles a small fortress city, allowed me inside only because I told him I wanted some brochures. The woman at the front desk was very personable, letting me check out the pool and private beach. Like a kid left alone in a toy store, I started grabbing whatever I could. My treasures included an engraved plastic cup that I filled with pineapple-infused water. For a touch of class, I asked the pool-side bartender for a splash of lime. I let him squeeze it for me.

I set foot on the white sand but could not fully relax. The valet had the keys to my car, which I'd been told to park by the front entrance, since I wasn't going to be long. So, after getting a refill of water, I returned to the car to retrieve my keys from Dane. He explained that my impressions were correct: The island is dominated by resorts and rental homes with private beach access. Most guests eat at their resorts, whose dining spots are closed to the public. Longboat does have a few restaurants (he could name only three), though many visitors drive to Anna Maria or St. Armands for meals.

For a public beach, he told me to look for the small blue signs along the road. There are five; I struggled to find one. When I finally located it, I tossed down a towel, then built a cup holder out of sand for my Longboat Key Club and Resort souvenir.

St. Armands Key and City Island

Shop by land, eco-tour by sea

Shopping is more of a necessity than a frivolity on Longboat Key, where the main stores stock groceries and pharmaceuticals. Visitors with the itch to spend travel a few miles south to St. Armands Key, a former mangrove forest developed by circus king John Ringling in the first half of the 20th century.

St. Armands Circle features a rotary of stores with a park in the middle. Along one curbside segment, plaques pay tribute to such bygone talents of the big top as aerialist Lalage, the so-called High Priestess of Rhythm Aloft, and Mabel Stark, who controlled 21 tigers and lions without suffering a bite.

The stores are divided into four color-coded quadrants. In purple, I found R&R Bond Galleries, a purveyor of Salvador Dalí sculptures and fine arts. As I pondered Woman Aflame, envying the drawers built into her body, I was joined by owner Richard Priess. He provided a quick art history lesson that touched on the woman's vicissitudes, which she stores in the compartments and that lead to her downfall. For an encore, he described his own hardships.

"This is supposed to be like Palm Beach's Worth Avenue," the dapper Austrian said. "I thought there would be more jewelry stores or designer stores like Fendi or Dior. But instead, we have island beach places like ice cream shops and T-shirt stores."

I freed myself from the retail whirlpool by jumping aboard an eco-tour at Mote Marine Laboratory and Aquarium, on City Island between Longboat and St. Armands Keys. The tour boat plies Sarasota Bay, and while we were supposed to be learning about the ecology, marine biologist Noah Hansen peppered his talk with real estate ephemera. He showed us a mansion with a rooftop tennis court, described the guitar-shaped pool of AC/DC's lead singer (a resident of nearby Bird Key), and pointed out a camera in a resident's yard. The video is not for security, he explained; we were streaming live on Seesarasotalive.com. Hi, Mom!

For the last portion of the ride, Hansen netted a cross-section of bay life for our inspection, including a sea squirt and a garlic sponge that smelled like an Italian kitchen. Frequently, he used a food critic's vocabulary to describe the fish: Snapper was "quite scrumptious," stone crab claws were "delicious," and pink shrimp "are what you eat when you order shrimp."


Siesta and Casey Keys

Beach-party vibe vs. mellow beat

Most locals I had met expressed fealty to their island. Yet, when it came to sand, they deferred to Siesta Key Beach. Even Dr. Beach has apparently fallen for its charms, ranking it as the world's No. 2 strand after Kauai.

What makes the sand so special is that it's 99 percent quartz, cool even in the swelter of summer and so soft you can powder a baby's tushie with it. "We go to different beaches every day," said Florida mainlander Karen Goloboski, who was accompanied by her 4-year-old son and a gal pal. "I would give this beach a nine."

Since the beach is 21/2 miles long and 150 yards at its widest point, I needed some extra power to properly cover the strip. Biking is permitted on the hard-packed sand; the main obstacles were sand castles, holes dug to China, prostrate sunbathers as dark as beef jerky, and flocks of birds standing in formation.

When I dead-ended at the northern tip, I veered toward Siesta Key Village, a spray of shops of the beach-party variety. At the Daiquiri Deck, slushie-style machines line the back wall, churning out more than a dozen flavors of the tropical cocktail. The signature drink is the Decksickle, a liver-challenging combination of piña colada and Deck Diesel, which is orange grain alcohol plus vodka. It is supposed to evoke an orange creamsicle, but it reminded me of the flavored cough medicine my mother used to pour down my throat.

On Sundays, dozens of musicians form a drum circle on the beach, composing a musical score for the setting sun. The event can attract as many as a thousand people, one performer told me, and sometimes turns into a spectacle approaching a John Cage-conducted bacchanal. The numbers are much smaller - and the scene mellower - on Casey Key, which holds two drum circles a week, on Wednesday and Saturday.

Casey Key is mainly residential, with enviable homes that seem untouched by the pox of foreclosures. (Stephen King is a winter resident.) Many of the estates on the Intracoastal Waterway side of the street have private wooden boardwalks that lead to the Gulf. Public footprints are not welcome. Nokomis Beach, however, could not be more populist, especially on drum circle nights.

"We are celebrating life, and the sun is part of it," said James Haydon, one of two conch blowers that evening. "The drum circle is the kind of place that brings together every nationality, every culture, every kind of person."

Performers sat on the sand or in beach chairs, drums wedged between their legs. In the center of the O, a shaman dressed in a white, sleeveless shirt and a fancy topper blessed the circle with two feathers from a great blue heron. A belly dancer swung her hips and snaked her arms toward the reddening sky. On the outer rim, spectators watched the scene as they dug into their Tupperware dinners of pasta salad.

When the sun was seconds away from its final descent, the shaman and Haydon raised their shells and blew to the north, south, east, and finally, west. "This is a sacred space," the shaman said before dancing off into the dusk.



Really old Florida

Let me just get it out there: Venice is old. But I don't mean in the senior sense. Though the island is ranked as one of the top retirement communities in the country and the average age is 68, the town is also a paragon of historic preservation.

"You still find the original Venice and many of the homes from the 1920s, '30s and '40s," said K.C. Quaretti-Lee, executive director of Venice MainStreet, a volunteer organization that works to maintain Venice's small-town atmosphere. "We want Venice to look the way Venice has always looked."

In the small downtown - a trifecta of streets - Lee drove me past the Venice Center Mall, a stuccoed structure that in the 1930s was the winter headquarters of the Kentucky Military Institute, and the cotton-candy-pink Venice Theater, built as a garage in 1927. Near Circus Bridge, a historic plaque describes the Ringling connection to Venice: In 1960, the circus relocated its winter home from Sarasota to the barrier island.

"Oh, it was such a sight to see the performers and animals walk over the bridge and through town to their homes. So many people came out to see us," said Tito Gaona, a 17-year trapeze artist who performed with the First Family of the Air and now runs a trapeze school in town. "Venice has a lot of circus history behind it."

The circus packed up in 1992, but the swells of people have not dispersed. On any given day, you'll find folks picking through the sand looking for prehistoric sharks' teeth. This is the Shark Tooth Capital of the World, after all.

I had heard that Caspersen Beach was a dumping ground of teeth. Standing on the water's edge, I peered down at a swirling mosaic of white and black fragments. I grabbed for the dark specimens, only to be tricked by rocks. After a fruitless half-hour, I asked two women walking a dog whether they'd had any luck. One woman pulled four teeth from her T-shirt pocket, all found that morning. Her friend offered some guidance: "You have to wait for the waves to bring them in and then grab them. If they go out again, they won't come back. You also have to know what you're looking for" - basically, vampires' baby teeth. Bolstered, I spent 15 more minutes wading around the shallows, surrounded by discarded shards. But then I brightened, figuring that I probably could buy some teeth in town.


Manasota Key

Just beachy

By the time I hit Manasota Key, I had forgotten about sharks' teeth. In fact, I stopped thinking entirely. The island did not have the mangrove kayaking of Anna Maria, the gated communities of Longboat, the shopping of St. Armands, the marine eco-tours of City Island, the beach biking of Siesta, the drums of Casey, or the history and fish orthodontics of Venice. It did, however, have four beaches spread over one square mile.

At Stump Pass Beach State Park, on the southernmost point, I tossed down my belongings and jumped into the cool water. I swam out to where I could glimpse the next key in line, Palm Island. Then I floated back to the only Gulf island that, for the moment, mattered.


Hopping the Gulf Islands

Places to stay

Tortuga Inn Beach Resort

1325 Gulf Dr. N.

Anna Maria Island



Spacious rooms with tasteful Old Florida decor. Across the street from the beach. Rates from $120, depending on season and hotel type.

Banana Bay Club

8254 Midnight Pass Rd.

Siesta Key



Full-service villas, apartments and cottages at two locations: on a lagoon (free use of kayaks and canoes) or near Crescent Beach. Rates from $89, depending on season and type of accommodation.

Inn at the Beach

725 W. Venice Ave.




Charming lodging across the street from the beach (the island's only hotel with such proximity) and within walking distance of town. Rates from $138, breakfast included.

Places to eat

Sandbar Restaurant

100 Spring Ave.

Anna Maria Island



Sit outside for Gulf views and sunsets. Seafood is the main event (dinner plates from $20), but burgers, pasta, and other entrees are also available.

Euphemia Haye

5540 Gulf of Mexico Dr.

Longboat Key



Upscale surf and turf, including snails with braised mushrooms ($11.50), pumpkin rum bisque ($8.75), snapper with pistachios ($30.75), and poached veal sweetbreads ($26.25). More casual dining upstairs at the Haye Loft, with gourmet pizzas, pies, and more.

Siesta Key Oyster Bar

5238 Ocean Blvd.

Siesta Key



An oyster bar, plus fried grouper bites, coconut shrimp Oriental salad, burgers, and flatbread pizzas. Dishes: $5 to $22.

Daiquiri Deck

5250 Ocean Blvd.

Siesta Key



Pair raw oysters, Gulf shrimp, and other edibles with a daiquiri concoction, such as the Critical Condition or Cheap Date. Daiquiris from $6.50.

Sharky's on the Pier

1600 Harbor Dr. S.




The island's only beachside restaurant. Seafood is the specialty. Entrees: $15 to $35.

Things to do

The Studio at Gulf and Pine

10101 Gulf Dr.

Anna Maria Island



Owned by Rhea Chiles, Florida's former first lady, the multipurpose space features art exhibits, lectures and classes.

Native Rentals

5416 Marina Dr.

Holmes Beach



Paddle a kayak on a self-guided tour of the area's mangrove swamps, salt marshes, and estuaries, such as Robinson Preserve. Four-hour rental, $29.

Sarasota Bay Explorers at Mote Aquarium

1600 Ken Thompson Pkwy.

City Island



Learn about the local marine and bird life on the Sea Life Encounter Cruise, which includes a short hike on Beer Can Island (formally known as Pine Key) and a touch tank with species found in the bay. $26 per person.

Siesta Sports Rentals

6551 Midnight Pass Rd.

Siesta Key



Rent a beach cruiser and bike on the packed sand of Siesta Key Beach or along the island's bike lanes. From $5 per hour, $10 for four hours, or $15 per day.

Drum Circle

Siesta Key Beach, Siesta Key


Nokomis Beach, Casey Key


Watch the sun drop to a percussion soundtrack Wednesdays and Saturdays on Nokomis Beach and Sundays on Siesta Key Beach. Free.

Stump Pass Beach State Park

Southern tip, Manasota Key



Admission: $3 per car

More information

Bradenton Area Convention and Visitors Bureau



Sarasota & Her Islands Convention & Visitors Bureau



- Andrea Sachs