Home of Pineland, Bokeelia, Matlacha, and St. James City

Southwest Florida was severely impacted by Hurricane Ian that came ashore on September 28, 2022.  Parts of Pine Island are still in the process of being rebuilt. 

By  Mike Miller  Updated August 18, 2023

Pine Island, Florida Things To Do, Lodging, Dining, Real Estate, At End Of Article

Pine Island, Florida is squeezed between Captiva Island and Sanibel Island on Florida's Gulf Coast, and the metropolitan areas of Cape Coral and Fort Myers on the mainland.

It is a step back into a part of Old Florida that is rapidly disappearing.

Map of Pine Island from, Southwest Florida Road TripsLocation Map of Pine Island, Florida

Located in Lee County, it is bordered by Pine Island Sound to its west and Matlacha Pass and Matlacha Island to the east.

Pine Island Sound is encircled by Pine Island and the barrier islands of Sanibel, Captiva, North Captiva and Cayo Costa.

These islands separate the sound from the Gulf of Mexico.

Pine Island Road is the only highway onto the island and it runs through Matlacha (pronounced Matt-La-Shay), an old historic fishing village.

Matlacha is a bit of a funky arts community that is hard to describe.  You can you stroll through the main street visiting quaint shops mixed with artist's displays.

There are colorful galleries, fresh seafood markets, and small restaurants.  Most of the time you will hear live music being played.

Bridge from Mainland to MatlachaBridge from Mainland to Matlacha

It was built on one of a series of small islands that were dredged up years ago to construct the bridges and road from the mainland to Pine Island.

These islands are in Matlacha Pass, the shallow body of water that separates Pine Island Florida from the mainland.

Although commercial fishing is not what it once was, fishing in the area is still a popular activity. 

This is so true that the Matlacha Bridge is nicknamed the "World's Fishingest Bridge."


The narrow bridge and roadway across Matlacha Pass and through the village are both an aggravation and a salvation.

The aggravation comes during tourist season when Pine Island Road can be backed up with traffic at times in Matlacha and for miles east and west.

The salvation could be that there seems to be no easy or economical way to solve the traffic problem.

Perfect Cup Restaurant in MatlachaPerfect Cup Restaurant in Matlacha. Jay Westendorf With Coffee

The road right-of-way through the historic district of Matlacha is only 66 feet wide.

To widen the road would destroy the village. To build another bridge and highway would cost a fortune that nobody at present is willing to spend.

The result could be a Pine Island that will remain less developed than the rest of Florida's Gulf Coast. 

There are no named beaches here and you won't find a high-rise development or big crowds.

The quiet Old Florida ambiance of Pine Island is the biggest reason people come to visit and then stay.  It has attracted at least 9,000 permanent residents. 

Current and former residents include well known Florida authors Robert N. Macomber, who lives in St. James City and Randy Wayne White (who lived in Pineland but now lives on Captiva Island.)


Pine Island Rd. continues west through Matlacha for a few miles to an intersection with Stringfellow Road known as Pine Island Center.

Stringfellow is the main road forming a two lane north-south spine connecting the north end and south end of the island.

Pine Island Florida is still largely rural with large areas of farmland, pine forests and marshes.

It is populated by residential settlements at Bokeelia at the northern end of the island.

Heading south from Bokeelia you will come to Pineland and then St. James City which is on the southern end of the island.

All three of these are very small communities.

Your exploration of Pine Island begins at the Pine Island Center intersection.  Take your pick, north or south, and head that way.

If you go north you will come to Pineland Road. Take it west through the quiet countryside to the little community of Pineland.

You will know you are there when you see the old fashioned post office.

One time when I visited there a peahen on the porch of the building walked over to greet me. 

Pineland Marina is on the water west of the post office and is a popular place to catch a boat out to Useppa Island or Cabbage Key

The community of Pineland has a population of less than 500 people.  Tiny as it is, it has a long history and was one of the oldest native settlements in Florida.

It was a Calusa Indian village for more than 1500 years.

Pineland Post OfficePineland Post Office

Today you can visit the Randell Research Center dedicated to the archeology and history of the Calusa Indians.  The center is open to the public.

You can walk the Calusa Heritage Trail or take a guided tour to learn more about their culture and the region's history.

The trail is almost a mile long and takes visitors through the archaeological site, canals, and ancient shell mounds.

The largest mound has observation platforms at the top for a even better view of the island's natural beauty.

When you are ready to eat you can visit the Tarpon Lodge and Restaurant, a popular resort built in 1926.

North of Pineland on the northern tip of the island is the little village of Bokeelia with a magnificent view of Charlotte Harbor, Cayo Costa and Boca Grande.

A few old buildings remain and a long fishing pier is an attraction that draws people from all over the area.

Captain Con's Fish House, BokeeliaCaptain Con's Fish House, Bokeelia

Bokeelia is a collection of mobile homes, houses and small condos on the several canals that have been dredged into the island. It's good to have a boat in this part of Florida.

Capt'n Con's Fish House is a popular restaurant with great views north to the harbor and the fishing dock. There are also several small inns and rental cottages in Bokeelia.

The area is surrounded by natural preserves with miles of mangrove forest.

Farming of tropical fruits and tropical plants are among the main industries on the island.  There are acres of palm trees and fruit groves, including mangoes.

An 18-hole golf course, Alden Pines Country Club, is the only golf course on Pine Island.

From Bokeelia you will head south on Stringellow Road until you get down to St. James City on the very south tip of Pine Island.

St James City Drunkenmost City MarkerSt James City Drunkenmost City Marker

It's about a 16 mile trip and you will see acres of farmland and forest along the way.

The first structure of note you will see as you enter St. James City is the Ragged Ass Saloon on your right.

St. James is a small town but a little busier and more active than Bokeelia.

A sign in town says "We don't have a town drunk. We all take turns." 

It's a neat sign, but you will not feel threatened by the make believe outlaw image.

St James City Gift ShopSt James City Gift Shop

St. James City is a residential community with an interesting collection of waterfront mobile homes, Florida style houses on stilts, and an increasing number of McMansions that would look at home in any upscale Florida community.

The city is a popular destination for water lovers, with fishing and boating topping the list.  You will also find plenty of nature trails if you'd rather be on land.

Retaining its old Florida charm, St. James City is a great place to relax and enjoy a beautiful sunset.

St James City Low Key TikiSt James City Low Key Tiki


Tarpon Lodge Restaurant
13771 Waterfront Drive
Pineland, Florida 33922
Tel: 239-283-3999

Tarpon LodgeTarpon Lodge

Tarpon Lodge Restaurant and it's inn are in an historic 1926 building that captures the grandeur of the early days in Old Florida.

The dining room is bright and cheery, and both inside and outside dining areas are available.

It reminds me in a way of some of the nicer places I've been in the Family Islands of the Bahamas. The restaurant staff is friendly and know the menu very well.

You can come to this restaurant either by car, your own boat or from you room at the adjacent lodge. If you come during a cold snap in the winter try to get a table near the fireplace.

There is something for everybody on the menu, seafood lovers and landlubbers alike.

Appetizers are a great way to start, of course, and they have bruschetta, skewers of bronzed gulf shrimp, pork sliders, tenderloin tips, blackened fish bites, crab and corn chowder, and a wide soup selection.

Their Pine Island Salad uses local organic greens and spring mix topped with hearts of palm, fresh cucumber, red onions, grape tomatoes, kalamata olives, and walnuts all served with a citrus vinaigrette dressing.

Tarpon LodgeTarpon Lodge

The entrees include chicken and crab sauteed with crabmeat and Monterrey Jack cheese, slow roasted pork rib, filet mignon, Gulf shrimp scampi and the fresh catch of the day.

The catch of the day is sometimes a delicious local fish known as tripletail.

They also have scallops, lobster, and a high class macaroni and cheese dish that includes a medley of seafood such as shrimp, crab and fish topped with toasted bread crumbs and bacon crumbles.

The restaurant has a nice wine selection and a full bar.

This is a moderately upscale restaurant.

Although you don't have to wear a coat and tie or a tuxedo, it's best to dress a bit better than your normal wife beater tee shirt, ragged shorts and flip flops that are okay in the rest of Pine Island Florida.

The Tarpon Lodge Restaurant is open every day from 1130am to 9pm.

Interactive Google Map of Pine Island, Florida

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