Just past the Island Time Zone road sign, the tiny town of Matlacha (MAT-luh-shay)--an islet west of Ft. Myers--welcomes visitors with art galleries and shops but retains the charm of a quiet fishing village. Tethered to the mainland by the "fishingest bridge in the U.S.A." over Matlacha Pass, it's surrounded by dozens of mostly empty isles, an ideal habitat for fish (and the anglers who catch them). Kayakers come here to paddle placid backwaters, but be sure to spend time on dry land, checking out the eclectic collections at galleries such as Lovegrove Gallery & Gardens, where owner and artist Leoma Lovegrove's vibrant paintings cover every surface.
Route 78 from Matlacha continues to peaceful Pine Island. The land on this 17-mile-long slice of Old Florida is largely home to plantations replete with palm, citrus, avocado, guava, macadamia, and mango trees. (The island's annual Mango Mania festival--with games for the kids, recipe contests, and arts and crafts--will be held July 16-17; mangomaniafl.com)
Pine Island's sparse traffic--and the bike path running from one end to the other--makes it ideal for cycling. Hikers take the Calusa Heritage Trail, which winds among ancient shell mounds and the remnants of an impressive cross-island canal built by the Calusa Indians, who settled here around A.D. 1. Trail signs illustrate the thriving seaside village that greeted Spanish explorers in the early 1500's.
Stay: Tarpon Lodge offers waterside accommodations in the original 1926 inn and auxiliary buildings, plus fishing and boating day trips with osprey, egret, and dolphin sightings. Rates start at $125; 239-283-3999 or tarponlodge.com
Eat: The Tarpon serves always fresh (never frozen!) fish and outstanding blue crab-and-roasted corn chowder. Bert's Bar & Grill in Matlacha features tasty seafood, live music, and dockside dining; Great Licks Ice Cream Shop satisfies sweet tooths.
Play: Pine Island Cycles, Inc., rents beach cruisers ($15 per day); 239-560-0320. Gulf Coast Kayak provides opportunities to paddle the area's placid inlets, starting at $35 for half day; 239-283-1125 or gulfcoastkayak.com.