PINELAND/BOKEELIA
Tiny Pineland, found at the three-point convergence of Pine Island and Stringfellow roads, has amenities reserved for much larger places. There’s a post office (albeit one of the country’s smallest), a marina, a bible college, a marine research institute, an Indian archaeological site and even a golf course. Pineland also boasts a working novelist—Randy Wayne White. There’s a restaurant and hotel—the 1926 Tarpon Lodge and Restaurant, overlooking Pine Island Sound. Charters to the surrounding islands—Sanibel, Captiva, Useppa and Cabbage Key (a restaurant there is rumored to be Jimmy Buffet’s inspiration for Cheeseburger in Paradise)—are available at nearby Pineland Marina.

Bokeelia seems virtually undiscovered despite its port, restaurants (the Lazy Flamingo and Captain Cons, which serves fabulous grouper) and art galleries. Homes here embody Florida’s past—some have white picket fences, tin roofs, widow’s walks and wraparound porches for watching the sun set over Black Bay and Charlotte Harbor. Anglers say Bokeelia’s shallow waters are ideal for snook, trout and grouper.

SAN CARLOS PARK, THREE OAKS
Escalating home prices, proximity to the international airport and university, and a new shopping center (the mega Gulf Coast Town Center) have placed this south Lee County community on an upward spiral. Close to the major amenities of its larger neighbors—Fort Myers to the north and Bonita Springs to the south—San Carlos Park and Three Oaks are the ideal midpoint for folks who work in Naples and Fort Myers.

Many residents moved into San Carlos more than five years ago, when homes sold in the low $100,000s and attracted young families and first-time buyers. Two recreational facilities—the 36-acre Three Oaks Park and the Karl Drews Community Center—offer programs for children and adults, youth sports and playgrounds.

Baseball and soccer fields at Three Oaks Park stay busy most weekday and weekend nights. Many of the vacant lots from a few years ago now have homes. Lots in San Carlos tend to lack deed restrictions and city water and sewer service (a majority of homes use wells and septic tanks). Newer areas, like neighboring Three Oaks, have central water and sewer services and deed restrictions.

RURAL LEE COUNTY
Lee County’s rural edge is changing as gated communities along Palm Beach Boulevard/S.R. 80, once considered too far removed from the amenities of Fort Myers, are proliferating. Verandah, located along the Orange River, and River Hall, a 2,000-acre community by new-to-Southwest-Florida developer LandMar Group, take advantage of the slower way of life this area affords. Far-off towns like Alva and Buckingham have also kindled interest from buyers who want a more rural lifestyle and larger lots that can accommodate mini-ranches and horses.

Many of the homes in Fort Myers Shores, found along the south bank of the Caloosahatchee River east of S.R. 31, back into canals leading to the river. Travel farther east along S.R. 80 and signs of civilization and development relax. Land restrictions have kept vacant property in Buckingham, the site of a World War II Army training camp for airplane gunners, fairly large in size. Neighboring Olga is located on the Caloosahatchee. Development has followed with a new Publix-anchored shopping center at routes 80 and 31.

Recreational outlets are just miles apart—a marina at Sweetwater Landing, Hickey Creek Mitigation Park, Franklin Lock Recreational Area and the Caloosahatchee Regional Park, a 768-acre facility on the north shore with two walking trails, mountain bike and equestrian trails, primitive campsites and breathtaking views of the namesake river.

Collier County

Florida’s largest county, Collier, has shed its fishing-town persona for a more polished, sophisticated identity that often attracts celebrities and luminaries who shop, dine and vacation here. That’s not to say that you can’t still find a slower, Old Florida vibe in Collier County among the unspoiled mangroves and backwater bays along the Everglades and Ten Thousand Islands. While it still attracts its fair share of seasonal retired residents, Collier County is getting younger. In fact, those aged 25 to 49 are the fastest-growing population group, and the county’s median age has dropped to 43 in recent years.

The Gordon River and Wiggins Pass immortalize Collier County’s first modern-day settlers—Roger Gordon and Joe Wiggins, who arrived in Naples in the late 1860s. When Louisville Courier-Journal owner Walter Haldeman arrived in 1887, he and fellow well-heeled Kentuckians helped turn Naples into a winter playground for the rich and famous. The Naples Hotel soon became the social center for visiting celebrities, among them Thomas Edison, Harvey Firestone, Greta Garbo and Gary Cooper.

In the 1920s, Barron Gift Collier bought more than a million acres of swampland, including most of Naples. He then pledged his own money to build the 275-mile Tamiami Trail, linking Tampa to Miami, which officially opened in April 1928. The completion of I-75 and the Southwest Florida International Airport some 60 years later put Collier County officially on the map. Today it’s a study in paradoxical worlds—stretches of beaches boasting multimillion-dollar mansions and luxury high-rises and quiet fishing communities that recall another time and place. Home prices in some areas now command more than $20 million—well above the $125 of a turn-of-last-century beachfront lot.

BEACHES
Consistently ranked among the world’s best, Collier County’s 17 miles of Gulf beaches can be reached within a half-hour drive from almost anywhere in the county. Forming a winding ribbon of shell-strewn white sand, the county’s coastline extends south from Barefoot Beach at the Lee County line to Marco Island, the largest of the area’s famed Ten Thousand Islands. The shore alternates between more than three miles of city and county beach parks, state preserves, neighborhoods of beachfront cottages, mansions, high-rises and the Gulf-front resorts in Naples. Travel south from Naples, and beaches give way to a mangrove-tangled coastline that signifies the beginning of the Everglades. Most beachfront homes are found in named communities, gated and non-gated. Those not directly on the Gulf are within an easy walk and boast something their beachfront siblings can’t—deep water for a prized boat-in-your-backyard lifestyle. Yet living on the beach comes with a cost: higher home prices, and some lack of privacy (all beaches are public).

Barefoot Beach is flanked by a county beach park and the 324-acre Barefoot Beach Preserve state park, where visitors are updated daily on wildlife sightings—everything from bottle-nose dolphins to sea turtles and gopher tortoises. The adjoining Bonita Springs beach access offers picnic and restroom amenities and wide, shell-crushed beaches.

Homes in Barefoot Beach, found in just a handful of neighborhoods, range from condominiums, villas, cottages and three- and four-story Mediterranean and Florida-style homes. "Homes have become bigger and more expensive over the years," says Barefoot Beach Realty’s Nick Fontana, who’s been selling Barefoot Beach property for nearly 20 years and has seen most of the neighborhood’s original beach cottages razed and replaced.

Vanderbilt Beach, south of Barefoot Beach, offers a multitude of waterfront options: single-family homes along canals, bays and the beach, and Gulf-front high-rises with views of the Gulf and Sanibel Island. Earlier this year, Signature Communities broke ground on a new luxury high-rise residential building, Moraya Bay Beach Tower, in the former location of local favorite Vanderbilt Inn, which was demolished at the end of 2006. The neighborhood demonstrates Southwest Florida’s ease in the art of juxtaposition; it’s sandwiched between the natural beauty of Delnor-Wiggins Pass State Park on the north and the cosmopolitan resorts, boutiques and restaurants to the south at Gulfshore Drive and Vanderbilt Beach Road, home to the Ritz-Carlton Beach Resort and Vanderbilt Beach Park.

Delnor-Wiggins Pass is coveted for its amenities that give visitors the opportunity to enjoy nature’s bounty, from snorkeling, sun worshipping and swimming to fishing and kayaking along estuaries and scuba diving the hard-bottom reef of the Gulf. Gulfshore Drive ends at Vanderbilt Beach’s southern boundary and is lined by condos, resorts and the occasional single-family home.

The 2,100-acre Pelican Bay community occupies the sprawling span of land between Vanderbilt Beach Road and Seagate Drive. Only a handful of luxury high-rises and The Strand, an exclusive triple-gated neighborhood of just a dozen multistory Mediterranean homes, enjoy an on-the-beach venue. Developer WCI Communities, however, brings the beach to Pelican Bay residents, who can opt for membership privileges in a private beach club.

Neighboring Clam Pass Beach Park marks the northern point of Naples proper and its 10 miles of beaches that earned kudos in 2005 from the Travel Channel as America’s Best All-Around Beach. Beaches stretch along Gulf Shore boulevards north and south from Seagate Drive to Gordon Pass, the southernmost point of the famous Port Royal neighborhood.

The coastal boulevard passes elegant high-rises, high-end resorts and restaurants, and offers glimpses of the Gulf between the homes—an eclectic mix of new estates and older cottages, some dating back to the late 1880s. Clam Pass’ three-quarter-mile boardwalk winds through scenic mangrove forests and over coastal dunes en route to the 35-acre county park, where amenities include picnic areas, rentals and a canoe launch. Naples Cay and Park Shore, just south of the Naples Grande, are mainly high-rise condo communities, offering a mix of old and new buildings.

Naples Cay is set on 33 acres of preserve and the white-sand beach of Clam Bay. Park Shore incorporates single-family homes and towers along Gulf Shore Boulevard North and the picturesque and oft-photographed Village on Venetian Bay, an upscale collection of restaurants, boutiques and galleries.

The northern sweep of Gulf Shore Boulevard takes in two of Naples’ oldest communities, The Moorings and Coquina Sands. Both feature mostly single-family homes (with some mid-rise condos) on larger landscaped lots (some waterfront) and homeowner associations with beach access.

The Moorings, Naples’ largest subdivision with more than 4,000 residents, 1,300 acres and 1,938 homes and apartments, offers many waterfront homes, including some with mile-long views to the Village on Venetian Bay, and frontage along Moorings Bay, which provides access to the Gulf at Doctors Pass. Homes in Coquina Sands are nestled along winding streets lined with ficus, banyan and palm trees and sidewalks for jogging, biking and walking. Close to the Fifth Avenue shopping district, the neighborhood is within walking distance of the resorts along Gulf Shore Boulevard.

Beach outposts in Naples include Lowdermilk Beach Park, offering shade trees, picnic tables, concessions and sand volleyball; public access points at the eastern boundaries of Naples’ east-west avenues; and the picturesque Naples Pier, which extends 1,000 feet into the Gulf and is found at the west end of 12th Avenue South.

The pier is especially popular with anglers; a bulk fishing license allows all to enjoy without an individual license. Gulf Shore Boulevard North assumes its southern coordinate at Central Avenue and rambles south passing old cottages and multimillion-dollar beachfront estates, hidden behind thick landscaping. Gulf Shore Boulevard South eventually becomes Gordon Drive, the western boundary of Port Royal and the Port Royal Club, one of the world’s most exclusive members-only clubs.

EVERGLADES CITY
Residents love Everglades City for what it doesn’t have—a shopping mall, a traffic light, high-rise condos, golf courses or any of the amenities of its more suburban Collier County siblings. The original county seat and the staging area for Barron Collier’s ambitious road-building undertaking (the Tamiami Trail), Everglades City is rich in history and prized for its natural setting, brushing up to the Everglades and Big Cypress National Preserve and set along the banks of Lake Placid and Chokoloskee Bay.

Yet with all this water, E.C. has no beaches. Inevitably, residents are lured by the rural, small-town Americana delivered by E.C., all two miles by four blocks of it, and its ample opportunities for outdoor recreation—fishing, boating or kayaking around the Ten Thousand Islands, or hiking and nature photography for landlubbers.

Everglades City becomes the center of the seafood universe each February with the annual Everglades Seafood Festival, featuring live music, rides, attractions and, you guessed it, seafood. Other nearby attractions include the Gulf Coast welcome center to Everglades National Park, the 11-mile Jane’s Memorial Scenic Drive in the Fakahatchee Strand State Preserve (home of the elusive ghost orchid) and Ochopee, where Everglades photographer Clyde Butcher hangs his shingle and displays his famous black-and-whites.

Everglades City and its surrounding environs feature a variety of residential offerings—sportsmen’s cabins and condos right on the water, million-dollar estates, Barron Collier-era cottages, mobile homes—and vacant lots. Prices range from nearly $200,000 to more than $1 million.

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