Best Golf Course: Tiburón (Naples) Finalists: Old Collier Golf Club (Naples), Olde Florida Golf Club (Naples)
Residents of  Tiburón golf community share their greens with guests of the Ritz-Carlton Golf Resort, Naples. The Greg Norman-designed Tiburón is tough enough for the most PGA-hardened pro while still enjoyable to your average duffer. To see the ultimate in swank private courses, beg or borrow (but don’t steal) tee times with a member friend at north Naples’ Old Collier Golf Club and Olde Florida Golf Club.

Best Community Park: Sun-N-Fun Lagoon at North Collier Regional Park (Naples) Finalist: Lovers Key State Park (Fort Myers Beach)
Splish-splash! There are wet and wild times to be had at Collier County’s new water attraction, which can also be rented for private parties. A state park with a loyal local following, Lovers Key has something for everyone, from serene spots for nature lovers to well-stocked concessions for families.

Best Local Entertainer: Janina Birtolo Finalists: Tim Poindexter, Danny Morgan
Melding her three passions, writing and acting and a fascination with famous women, Janina Birtolo has become a local stage force with her one-woman “conversations with history.” Kick back and get your groove on with a little sax on the beach from south Florida’s smoothest horn man, Tim Poindexter. Or if the Parrothead vibe is more your thing, catch Sanibel’s Danny Morgan.

Best Fishing Spot: The waters off Chokoloskee Island (Ten Thousand Islands) Finalist: Naples Pier
Chokoloskee is off the beaten path of your average pleasure cruiser, but well worth the trip for the serious angler. Several area charter captains take sportsmen into these waters, which teem with snook, tarpon, redfish and more. The rod-and-reel gang that hangs out at the Naples Pier has plenty of advice for would-be fishermen—listen to them, and you might land your own whopper. Or at least have one to tell.

Best Bird-Watching: Corkscrew Swamp Sanctuary (Naples) Finalists: J.N. “Ding” Darling Wildlife Refuge (Sanibel), Turner River Road (Naples)
Spoonbills, anhingas and the world’s largest nesting population of woodstorks are at home at Corkscrew Swamp Sanctuary, a rare and well-preserved habitat that serves as the local base for the National Audubon Society. No one could tire of the natural delights, winged and otherwise, at Sanibel’s “Ding” Darling Preserve, while serious birders get their binoculars out along Turner River Road off U.S. 41 in east Naples. (Just remember to let someone else drive.)

Best Scenic View: From Boca Grande Finalists: Hancock Bridge over the Caloosahatchee (Fort Myers), Marco’s Jolly Bridge
Not only is the singular Boca Grande a favorite vacation destination for presidents from Carter to the elder Bush, but once you stand on its shores and look back at the rest of the Gulfshore, you understand how magical this place we call home really is. Want to see for miles and miles? Cruise over Hancock Bridge to spy Fort Myers sprawling alongside the Caloosahatchee, or hit the Jolly Bridge to watch the sun set over Marco.

Social scene

Best Black-Tie Event: The Heart Ball Finalists: Edison-Ford Foundation Gala (Fort Myers), NCH’s Hospital Ball (Naples)
You’ve got to have heart, and the Gulfshore does, with two black-tie balls, one in each county, held to benefit the American Heart Association. The Edison-Ford Foundation Gala, which benefits restoration at the historic attraction, lights up the grounds of the inventor’s estate. One of the area’s oldest benefits, NCH’s Hospital Ball, is also one of its most glamorous.

Best Festival: Naples Winter Wine Festival Finalist: Everglades Seafood Festival (Everglades City)
From high-society to local flavor, these two festivals show just how well rounded the Gulfshore can be. The Naples Winter Wine Festival is the world’s most successful charity wine event ever, annually bringing in millions of dollars for kids in Southwest Florida. Everglades City rolls out the welcome wagon each February for thousands of tourists and locals to feast on stone crabs, fried gator nuggets and other delicacies.

Best Place to Be Seen: Port Royal Club (Naples) Finalists: Campiello Ristorante (Naples), The Veranda (Fort Myers)
The private club that does not like to see its name in print, the P.R.C., as we will call it, is an ultra-exclusive place to be spotted, whether you are working out at its deluxe new gym or dining at its Gulf-side tables. Snagging a good spot under the ficus tree in the Campiello courtyard will give your friends something to talk about, while a sharp suit and sharper line of patter will help you stand out from the power-heavy crowd at Fort Myers’ Veranda.

Best First Date Spot: Naples Pier Finalists: Muvico Coconut Point (Estero), The Turtle Club (Naples)
You’ll have to skip the jug of wine (alcohol being strictly prohibited on city beaches), but you can bring a loaf of bread and other picnic accoutrements to the beach by the Naples Pier, a perfect place to watch the sun set with a first date. At Naples’ Turtle Club, the Gulf murmurs sweet nothings while you dine at tables on the beach, and you can snuggle together for a movie’s scary parts at the palatial new Muvico at Estero’s Coconut Point.

Best Local Power: Couple Simone and Scott Lutgert (Naples) Finalists: Linda and Jim Malone (Naples)
He’s the laconic, get-er-done kind of guy, while she’s a bright spot of light on the Gulfshore scene. Together Scott and Simone Lutgert continue his family’s undeniable impact on the local business and charitable scene. Chairing the 2007 Naples Winter Wine Festival, Linda and Jim Malone surpassed expectations—and then surpassed them some more—raising more than $18 million.

Best Place to Dance: Noodles (Naples) Finalist: Sway (Naples)
Because you have to get rid of those rosemary-dusted garlic rolls somehow, on Thursday nights Noodles transforms itself from pasta purveyor to dance club, with a DJ manning the mix well after the clock strikes midnight. And no one will mind if you sway—ever so tastefully—on the center dance floor at the uber-trendy Sway Lounge.