IT’S A WATER WAY of life on Florida’s Islands on the southwest Paradise Coast. Every beach town has the essentials: brilliant sand, shimmering water and hypnotic allure, and its own unique identity. The mood along the coast shifts with the breeze from sophisticated metro to quirky beachside.
Day 1: Naples
Marco Island to Naples — 15.7 NM
Marco Island is the largest of the coast’s 10,000 islands where nature preserves shelter hundreds of mammals and birds including the American bald eagle.
Naples is famous for its sophisticated arts and culture, shopping, and dining. Despite its palpable swank, visitors appreciate the intimate, village vibe while strolling the tropically landscaped downtown streets dotted with sidewalk cafes, boutiques and art galleries.
Fifth Avenue South in Old Naples is one of the nation’s most exclusive addresses. Blooming tropical plants grace the walkways, and each shop window showcases chic fashion, jewelry and artwork tagged from reasonable to shocking prices. Mediterranean style Vergina restaurant has an elegant bar perfect for casual dining or sipping sophisticated spirits.
Since the 1930s, Third Street South has been a browsing favorite. Surrounded by the lovely houses and colorful beach cottages of Old Naples, shops and bistros are tucked among courtyards and antique fountains. Jane’s Garden Cafe on Third serves breakfast, lunch and Tea (English owners). The walls of residents’ favorite, Old Naples Pub, are covered in local history, and outside tables rest under a vine-covered canopy.
After dining at a posh beachfront resort or a funky bayside bar, head to Naples Beach and the iconic Naples Pier to witness a dazzling Gulf sunset. Nearby, the recently overhauled Port of the Islands Marina has direct access to Ten Thousand Islands, the Everglades backwaters and the Gulf, and accommodates boats to 65 feet. Naples City Dock’s new facility has 84 slips and 400 feet of side tie to accommodate various sized vessels.
Day 2: Fort Myers Beach
Naples to Fort Myers Beach — 16.5 NM
Bygone Florida is still apparent in Fort Myers Beach on six-mile long Estero Island. On the north shore, Times Square has a concentration of shops, restaurants and beach lovers. The Mound House museum reveals the history of the region’s indigenous people and early settlers atop an ancient Calusa Indian shell mound. The less crowded, southern end of the island has dozens of public-access beaches.
Nature lovers can wander the boardwalk through a live oak hammock and mangrove forest on Matanzas Pass Preserve, an unspoiled 60-acre bayfront sanctuary. The pavilion at the end overlooks Estero Bay Aquatic Preserve’s inhabitants — leaping fish, wading birds and an occasional bashful manatee.
Kayak the islands to the back bay along the 190-mile Great Calusa Blueway paddling trail. Inspired by the native Calusa tribe, the route meanders through the coastal waters and inland tributaries where the birdwatching is sublime, as are dolphin and manatee sightings.
Graze your day through the local seafood harvest of fresh fish, famous ‘pink gold’ (pink gulf shrimp) and delectable stone crab claws. Pause at Heavenly Biscuits for oven-fresh Southern biscuits with toppings or their outrageous cinnamon rolls.
The annual fall Tapa Hop Pub Crawl features several Fort Myers Beach restaurants providing tapas and appetizers to sample along with entertainment and prizes. Snook Bight Marina’s new floating slips for vessels up to 60 feet are a 500-yard walk to the beach. Boats up to 100 feet can dock at Pink Shell Beach Resort & Marina and enjoy amenities from swimming pools and spa to restaurants and a white sand beach.
Day 3: Captiva Island
Fort Myers Beach to Captiva — 23 NM
Captiva Island is a not-so-far-away exotic paradise where lavender flowers crawl across pristine, powdery sand. With an expansive background of sea, sand and sky, the island is all about the outdoors: biking, cruising, birding, golfing or simply lounging.
Quaint galleries filled with resident artists’ works give the village an intimate, almost magical feel. The 2 Islands Gallery at Chadwick’s Square is a whimsical place to shop for unique custom-made jewelry, pottery and island paintings created by area artisans. Their boutique section has stylish painted clothing, silk scarfs and lots more.
Dining choices range from beach shack to resort chic. The Bubble Room serves classic American cuisine with a side of smiles amid walls papered in memorabilia and the sounds of a working toy train. Linger after dinner at the casual beachside Mucky Duck to watch the sky transform during sunset.
South Seas Island Resort has a 330-acre wildlife preserve and two miles of beachfront. Dockage to 120 feet is available at the Yacht Harbour & Marina on Pine Island Sound. ‘Tween Waters Island Resort & Spa can accommodate boats to 100 feet.
EVERGLADES NATIONAL PARK protects an unparalleled landscape that provides habitat for rare and endangered species such as the West Indian manatee, American crocodile and the elusive Florida panther. This international treasure is a 1.5-million-acre maze of mangrove islands and waterways. A third of the park is navigable, but a tour out of Marco Island or Naples is the simplest, safest way to explore. Tour options include kayaking, slogging through water on foot, or taking a nature walk with a guide. All visitors thrill to an airboat ride far from land, out over the vast expanse often called the River of Grass.