24.5 million years ago, Pine Island rose, as did Florida, from the receding seas. It is not known when man first arrived on this island, but skeleton remains have been unearthed dating back about 6,000 years.

Calusa Indians were thought to have inhabited the island in peace from 300 AD until 1513 when it's believed Ponce De Leon landed on the west side of Pine Island. The Spanish not only fought the Calusas but introduced diseases they had no immunity to, wiping them out by the 1700's. An important archeological dig is located in Pineland, a small community on northwest Pine Island, thought to have been the center of the Calusa civilization.

Except for the occasional pirate or fisherman, Pine Island was then basically uninhabited until 1873. Those hardy settlers who then arrived, lived off the sea and carved out the paradise that we now enjoy.

 The Communities of Pine Island

Greater Pine Island consists of five communities, each with its own flavor, and the areas in between. First we entice you visually. You are probably coming from elsewhere in Southwest Florida, from Naples, Lehigh Acres, Cape Coral, Fort Myers, Port Charlotte- each nice areas in their own way, but each with a bit too much urbanization, too much traffic, too many rules and a feeling of sameness.

 Matlacha - Florida's "Fishinest Bridge"

First thing you notice when you travel to Greater Pine Island is Matlacha (pronounced Mat-luh-shay), a hodgepodge of the different. Your eyes will notice the great expanse of water, which backs up to almost every home and business. Each home and business is something different reflecting the personality and/or idiosyncrasies of the resident within or business owner. One likes bright colors and “pizzazz”, the other likes the more subdued. Here you will find houses, bars, art galleries, a post office, restaurants, a pet grooming service, gift shops, marinas, bait shops, a convenience store, motels, a small condominium, all sitting one next to the other in harmony. One house is large, one is a cottage, there’s a trailer, this one has dolls and giant stuffed animals on display, not to sell, but to show you. There is an old Indian statue sitting on a chair on the street wishing you a Happy 4th of July or a Happy whatever, depending on the season.

 Pine Island Center is Pine Island’s "downtown." Here you will find a large super market and shopping center. There is another smaller newer shopping center built in Old Florida style. A third shopping plaza features an old round historic building with several smaller shops and an art gallery in the rear. The plaza was once a motel and restaurant. Pine Island Center features a fairly new Old Florida style medical and professional center. It also features our fast food restaurants, barbecue, pizza parlor and other eateries. There are boat lift builders, a hardware store, beauty shops, a barber shop, a travel office, our four island banks, a do-it-yourself car wash, real estate offices, insurance services, accounting services, churches, two convenience stores, two pharmacies, some light industries, storage facilities, laundry, veterinary services, dentists, attorneys, etc. There is no post office at the Center. Every other community of Pine Island has its own post office, but not “downtown”. Oh, by the way, there is not a traffic light in Pine Island Center or in any of Pine Island for that matter.

Pine Island Center is also home to a beautiful public library in a relatively new building. It is used by ordinary folk as well as students and by many local resident authors for research. The old library building still stands. It is now a museum which concentrates on local history, especially that of the Calusa Indians who once had their capital on Pine Island. Two parks are in Pine Island Center. One is for quiet and maybe lunch. The Pine Island Garden Center created this “passive” park on donated land. The other is Phillips Park, a County facility, which features a huge swimming pool open to the public for a small fee as well as lighted tennis courts at no fee to the users. At the very end of Pine Island Road easily visible to the public is an osprey nest, the pride of the nice housing community immediately to its right.

 Go south from the Center toward St. James “City”. You will see a smattering of houses and two mobile home communities along the way as well as the VFW, American Legion and the Moose Club. Stop in for a “cool one” if you are a member. All along the road you will see mango groves, nurseries and acres of palm groves. On the left is the Pine Island Resort, a camping/RV facility. You can hike or bicycle the entire distance on a newly constructed off the road concrete bike path complete with safety rails.
St. James City

As you enter St. James City, you will pass the entrance to St. Jude’s Harbor, which is also the entrance to the Calusa Land Trust’s St. Jude Nature Trail. Here you can hike or bicycle through the woods and wetlands to the waters of Matlacha Pass over ground and over wood decking. Observe the native flora and fauna along this half-mile trail.

St. James City is Pine Island’s most heavily populated area. It was incorporated before Ft. Myers. But, showing itself in true Pine Island character, it “dis-incorporated” itself some time ago. It, too, is a mix of people, mostly a mix of retired residents, many who maintain two homes, one in St. James and one “up North”. You’ll see modest mobile homes, luxurious concrete block and piling homes, vacation cottages, and a small amount of condominiums and motels. None of the condos are over 38 feet tall (one of Pine Island’s few rules). Almost everything is waterfront. This is a boater’s community. The water is deep and Gulf access is easy. There are some good places to eat, some offering frequent entertainment. Pine Island is home to a many songwriters and musicians. They seem to congregate in Saint James, and can frequently be heard in parking lot "concerts."

 In Between Communities - North

Go North from Pine Island Center toward Bokeelia (about eight miles) at Charlotte Harbor. The paved bicycle path continues north along the edge of Stringfellow Road, offering a safe place to bike or walk. Along the way you will find some small businesses, a gallery with working pottery shed, a few churches, a restaurant or two, a mobile home park, but mostly you will see specialized agriculture. Here are Pine Islanders defying the American trend of abandoning the farm. They are intent to make it “farming”. And proud they are with unique crops and methods. There are growers of hybrid hibiscus, organic vegetable growers, growers of all kinds of palms, mango, lychee and other tropical fruit . You can buy some of the products at produce stands or in their nurseries. Pine Island mangoes are known throughout Florida. Pine Islands palms are shipped worldwide. If you happen to travel to Kuwait City or the United Arab Emirates, you’ll probably see palms that were born in Pine Island. Stop in one of the nurseries along the way to take home one of the palms or tropical fruit trees or to learn more about them.

 Bokeelia

Arrive in the Bokeelia area. Here you can spend some time looking at the waters of Charlotte Harbor. On good clear days you can see right across this large water to Cape Haze and Boca Grande Pass where the Gulf meets the Harbor. Bicycle or walk through Bokeelia rich in pirate history. Enjoy the scenery of nice homes, nicely landscaped short rise condominiums, vacation residences, art galleries, marinas, etc. Spend some money to spend some time on the long pier where you can drop your fishing line. Enjoy a meal on or across from the water, take a day cruise to Cayo Costa State Park with its seven miles of beach and multitudes of sand dollars. Cruise to Cabbage Key for lunch. Leave the money on the wall! Stay at one of the fine condominiums or motels or cottages in Bokeelia for a relaxing couple of days or longer. Go boating on your own; rent a kayak or canoe. Buy fresh shrimp or fish from one of the commercial fishermen who have long called Bokeelia home. Hire a Captain to take you or your group fishing, boating or to a secluded beach on one of the outer islands where you can swim, bask in the sun, frolic or picnic. Talk with the residents or fellow visitors. Bokeelia also features a diversity of people of various outlooks, interests and income levels living together harmoniously. Each February/ March "Music on Pine Island" offers a series of concerts in beautiful Fritts Park, featuring classical, pop and jazz. Plan to attend one or two or all.

 Pineland

Travel North from Pine Island Center and take a left onto Pineland Road. For your safety, there’s a new left turn lane at this intersection. Follow the winding road to arrive at Pineland. Agriculture gives way to history along this road. At the first curve you’ll pass a small reddish residence which at one time housed a church, then a school for the early pioneers to Pine Island. There is an old cemetery on the grounds, but it is not open to the public. Further on down is one of the smallest post offices in Florida. Stop in and say hello to the postmistress who runs this building totally on her own. In addition to regular postal duties, she maintains the facility and is responsible for keeping up the grounds, fixing and installing PO boxes, painting, cleaning, etc. She takes a one-hour lunch break so you can’t do business between noon and 1pm.

Leave the post office and travel Pineland Road west. Look to the right and you will notice the land elevation rises. All to your right are the remnants of the mounds of the capital of the Calusa Indian Empire. The Calusa controlled from Marco Island north to the present city of Sarasota and are credited at having dominated some areas all the way to what is now West Palm Beach. They had a remarkable system of man-made canals, some of which are still visible in Pineland and in the Pine Island Ridge area just east of Pineland. The turn of the century pioneers of Pineland built their houses on the Indian mounds for the great vistas of Pine Island Sound and the barrier islands you see on your left as the road curves. There is a small park on your left with an historical marker, which you can read. Take some pictures. Drive a bit again and observe some dazzling old Jamaican tall coconut palms near the 1926 historic Tarpon Lodge. Across the road from the large marina is the unimposing entrance to the Calusa Heritage Trail archeological site, where there is a teaching pavilion and gift shop.

The Center is operated by the University of Florida which is doing substantial digs on the grounds to study the history of the Indians who built them and then disappeared. Group tours are offered each Wednesday morning at 10 AM. The trail is open every day of the year except Thanksgiving and Christmas. Finally, you drive into Alden Pines, Pine Island’s only golf course community with beautiful homes, many elevated, backing up to the golf course. The golf course is open to the public at fairly reasonable rates. So, if you are into the sport, try your luck here. While you are golfing, you will be in a nature lover’s paradise sharing your space with osprey, eagles, even pond alligators.

We haven't covered it all. You can see that Greater Pine Island may be “off the beaten path” but it does offer worthy sites to see and a variety of things to do. Pine Island has been called “The Forgotten Island” in the past. Now because of MangoMania and our other attractions, and because of its “different than the rest” aura, we don’t think you will forget Pine Island anymore. With the abundance of writers, artists, and musicians Pine Island has become known as "Florida's Creative Coast."