Mayberry-like, quirky and infused with the spirit of artists from the past and present, Pine Island takes you on a trip back in time. Greater Pine Island is made up of five communities, each with its own distinct personality.
Matlacha
Tiny Matlacha (pronounced Mat-luh-SHAY) forms a bridge from the mainland to Pine Island, which, like Sanibel and Captiva islands, has only stop signs and courtesy to organize the flow of traffic. Matlacha occupies its own small island with a jumble of colorful shops and galleries, seafood markets, funky waterside restaurants and a community park that fronts Matlacha Pass, part of the Great Calusa Blueway paddling trail.
The most bustling of the five towns, Matlacha is the heart of the island’s artist community. Galleries in bright colors line Pine Island Road, while in the background shrimp trawlers and other fishing boats bob in the harbor. The boats haul fresh seafood to Matlacha’s seafood markets and waterfront eateries.
Pine Island Center
Pine Island Center, the hub of the island, serves as a business and community center – it includes a park and historical museum. It is a crossroads community roughly in the middle of 17-mile-long Pine Island, poised where Pine Island Road meets Stringfellow Road. Turn left at the four-way stop to get to St. James City or right to reach Pineland and Bokeelia. A paved bike path parallels the length of Stringfellow.
Historic St. James City
Historic St. James City at the southern tip of the island is home to fisherfolk, marinas, houses lining canals, waterfront restaurants popular with boaters and a handful of stores. Vast preserved acreage of sea and islands surround St. James City and stretch to the island’s northern reaches. Pine Island National Wildlife Refuge protects 17 mangrove islands in Pine Island Sound as rookeries and refuge for birds and other wildlife. Pine Island Aquatic Preserve encompasses 54,000 acres of submerged land.
Pineland
North of Pine Island Center, Pineland has been inhabited for thousands of years, originally by Calusa Indians, who built an important settlement here on the waterfront. Today, Calusa Heritage Trail at Randell Research Center lets visitors peek into their ancient world, learn about their sophisticated canal system, climb one of their mounds, and, on certain occasions, even witness an archaeological dig. Artistic, detailed signage tells the story of their long tenure here. Tours comprise land exploration of Calusa territory. A historic lodge and restaurant, a marina and 18-hole Alden Pines golf course also draw visitors to the quiet little village.
Bokeelia
Bokeelia, at the northern tip of Pine Island, has a similarly isolated feel, with a seafood restaurant, art gallery and historic B&B. The drive to Bokeelia along Stringfellow Road passes palm tree, tropical fruit and other landscape and food plant farms. The island is known especially for its mangoes, which inspire an annual festival in July. Roadside stands sell them during their summer season, along with lychees, longans, guava and other exotic fruits.
Bokeelia and Pineland are also launching points for fishing charters and trips to Cayo Costa, North Captiva and Cabbage Key – charming islands accessible only by boat.
