author Terri James: (239) 851-2356

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Driving to Pine Island, you drive through a small island community called Matlacha (pronounced: Mat-la-shay). This eclectic island gives you the feel that you have just entered the island life! There are art galleries  gift shops, restaurants, bars, seafood shops, waterfront inns, etc. Many of these businesses are world renown, ! Tourists come here from all over the world! There is a draw bridge, our one way on and one way off the island.  In the winter months, it can get congested in Matlacha, so take your time and do not be in a hurry. Many of the homes along Pine Island Road were built by “squatters” in the 1940’s and are now considered historic properties. Almost all homes and business in Matlacha are located on the water. There are many mangroves and islands around Matlacha, making for some wonderful kayaking and canoeing. There is a Lee County Boat Ramp available.

For more information, please go to:,_Florida .


Driving further to the west, you drive across Little Pine Island, which is about 3 miles wide.  This island is owned by the State of Florida as a preserve.  Currently, there is a restoration project in place to remove all exotic vegetation, leaving room for only native plants.  There are nature trails and birdwatching,

Anything north of Pine Island Road is considered Bokeelia, and anything south of Pine Island Road is St. James City.


Pine Island is about 17 miles long and approximately 3 miles wide at its widest point.  Pine Island Road ends in what is known as Pine Island Center, (aka ‘the 4 way’). We are very excited to now have 2 gas stations, with the addition of the new 7-Eleven in Sept. 2019.   The “Center” is where you will find the shopping center (Winn Dixie, CVS, restaurants), gas stations, hardware store, medical and professional plaza, public library, heated swimming pool, tennis courts, ball fields, fire station, elementary school, churches, other businesses, and some restaurants.


There is a community on the west side of Stringfellow Road, via Pineland Road, known as Pineland.  There is a very small post office (over 100 years old) on your way to Waterfront Drive, where there are amazing views of Captiva Pass and the Gulf of Mexico, especially at sunset!  Just around the curve, you will see a small parking area on the waterside where many people put their kayaks and canoes into Pine Island Sound.

You will notice the mounds high above the road in this area.  This is one of the highest natural points in Lee County.

This location is one of the areas for travel to the outer island, including Cayo Costa, , Upper Captiva, ,  Useppa, , and Cabbage Key, .  The Gulf of Mexico is easily accessed through Boca Grande Pass, Captiva Pass, or Redfish Pass via Pineland Marina, .

At the next curve heading north, you will find on your left, Tarpon Lodge, a four star restaurant and lodge in a historic building, Pineland marina, and on the right the Randell Research Center (a permanent archaeology research and educational project of the Florida Museum of Natural History, since 1983.)  The entrance to the Calusa Heritage Trail archeological site is just across from Pineland Marina, and is operated by the University of Florida.  They do have tours, so for more information, visit their website: .

If you continue north from Waterfront Drive, you will reach the Alden Pines Golf Course community.  This is the only golf course on Pine Island.  For information regarding tee times, etc., please call, 239-283-2179.

For additional information, please go to:,_Florida .


Bokeelia, on the north end of Pine Island is bordered by Charlotte Harbor on the north, Matlacha Pass on the east, and Pine Island Sound to the west, with views of Boca Grande, the “tarpon fishing capital of the world” and the Gulf of Mexico to the west!  Along Main Street, you will see a historic home, that is now the Lahser House, .  Bokeelia has a large marina, restaurants, and most of the condominium complexes that the island offers.   There are also residential neighborhoods, with Captains Cove being one of the two residential subdivisions on the island on private sewer.  There are several waterfront canal homes on the north end, and Charlotte Shores subdivision on the right side of Stringfellow Road, and south of Marina Drive.  This subdivision has a boat ramp for those living there off water.

There are boat rentals available at the Four Winds Marina, .  Lee County has a public boat ramp on the east side of Barrancas,  This is one of the locations for travel to the outer islands.  Cayo Costa State Park is only a few minutes away by boat,,

Bokeelia is home to many palm tree groves and tropical fruit and vegetable farms.  This is very much an agricultural community.

Bokeelia has some preserve land and trails.

For more information, please go to:,_Florida .


St. James City located on the south is the most populated area of Pine Island.   There is a gated off water community on the east side of Stringfellow Road.  Just past this on the west side, you will see Maria Drive, where you will find a Lee County commercial boat ramp, only available on weekends to the public, .  Traveling south, you will find several “dirt” roads to the east and west with residential homes, some with acreage.  On the west side further south is Flamingo Bay and Pine Island Cove.  Flamingo Bay is a volunteer HOA with membership to their clubhouse, pool and boat ramp.  This subdivision is a mixture of single family and mobile homes, all on septic.  Pine Island Cove is a 55+ mobile home HOA mandated community (all on private sewer) with some waterfront mobile homes, plus a community boat ramp with quick access to Pine Island Sound and the Gulf of Mexico.

Tropical Homesites subdivision has single family homes and available building lots.  Most lots are at least 1/3 acre and all are on paved streets.  Just south, Manatee Bay is on the east side of Stringfellow Road.  This is a deed restricted waterfront community, with a boat ramp for those living on the off water side of Manatee Dr.

Pine Island has a KOA campsite just south on the east side, .

Traveling further south, you will see St. Jude Harbors.  This is a residential community, with mostly waterfront homes.  There is also nature trail, just past Crestwell Dr. on the left

Across Stringfellow Rd., just before York Rd., you will find Galt Island Preserve, see

As you cross the small bridge into St. James City, you will notice several restaurants, many of which host local musicians throughout the year, along Stringfellow Road, which turns into Oleander Street at the entrance to Sanibel Blvd.  There are several residential neighborhoods, including 2 gated communities, and mobile home parks in St. James City.  For more information on any of these properties, just e-mail me from the link at the top of the page.  If you make it to the south end of the island, you can see San Carlos Bay, the Intracoastal Waterway, Sanibel, the causeways between Sanibel and Ft. Myers, and on a clear day, you can see Ft. Myers Beach!  There are a couple of condominium complexes (as I stated earlier, Bokeelia has the majority of the condos).

For more information, please go to:,_Florida .

If you have other questions that are not answered here, please do not hesitate to contact me for more information or a map of the island.