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. I have reviewed the restaurant towards the bottom of this page.

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, was the only golf course on Pine Island. It has been temporarily closed since Hurricane Ian in 2022.

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. It's been permanently closed since Hurricane Ian.

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.


Randell Research Center
13810 Waterfront Dr, Bokeelia, FL 33922 | (239) 283-2157

Randell Research Center, mentioned earlier, is a fascinating archaeological site on Pine Island. We enjoy exploring the ancient shell mounds and learning about the Calusa Indians who once lived here.

Visitors like the informative guided tours and educational exhibits. The walking trails are peaceful and scenic, offering glimpses of local wildlife. It’s a great place to connect with Florida’s rich history and natural beauty.

The knowledgeable staff is always ready to share interesting facts and stories. It’s a must-visit for history buffs and nature lovers alike.

Museum of the Islands
5728 Sesame Dr, Bokeelia, FL 33922 | (239) 283-1525

The Museum of the Islands is a charming place that showcases the history of Pine Island. We enjoy the diverse exhibits, which include everything from Native American artifacts to local fishing history.

Visitors like the friendly volunteers who are eager to share stories and insights. The museum also features interesting displays on the island’s agriculture and pioneer life. It’s a delightful spot to learn about the community and its heritage. The relaxed atmosphere makes it an enjoyable visit for all ages.

Matlacha Pass Aquatic Preserve
12301 Burnt Store Rd, Punta Gorda, FL 33955 | (941) 575-5861

Matlacha Pass Aquatic Preserve back in Punta Gorda is a paradise for nature lovers. We enjoy kayaking through the mangrove tunnels and exploring the serene waters.

Visitors like the abundant wildlife, including manatees, dolphins, and a variety of bird species. The preserve is perfect for fishing, boating, and birdwatching. The peaceful environment offers a wonderful escape from the hustle and bustle.

It’s a great place to immerse yourself in the natural beauty of Pine Island. The preserve’s pristine waters and lush surroundings make it a favorite spot for outdoor enthusiasts.

Bokeelia Fishing Pier
8421 Main St, Bokeelia, FL 33922 | (239) 283-2244

Bokeelia Fishing Pier is a fantastic spot for anglers. Visitors enjoy casting their lines and relaxing by the water. We like the stunning views of Charlotte Harbor and the chance to catch a variety of fish.

The pier is also a great place to watch the sunset and enjoy the peaceful ambiance. It’s a popular spot for both locals and tourists. The friendly atmosphere and beautiful scenery make it a perfect place to spend a leisurely afternoon.

Whether you’re an avid fisherman or just enjoy being by the water, the Bokeelia Fishing Pier is a must-visit.

Four Winds Marina
16501 Stringfellow Rd, Bokeelia, FL 33922 | (239) 283-0250

Four Winds Marina is a top spot for boating enthusiasts. We enjoy renting boats and exploring the surrounding waters. Visitors like the friendly staff and excellent facilities. The marina offers easy access to great fishing spots and beautiful islands.

It’s a convenient and well-maintained place to launch your adventures. The marina also features a bait shop and a waterfront restaurant.

It’s a great place to start your day on the water or relax after a day of boating. The scenic location and helpful services make it a favorite among locals and visitors.

Gallery Of Matlacha
4625 Pine Island Rd NW, Matlacha, FL 33993 | (443) 350-3188

Gallery Of Matlacha is a vibrant showcase of local art. We enjoy browsing the diverse works, including paintings, sculptures, and handmade jewelry.

Visitors like the chance to meet the artists and learn about their creative processes. The gallery is colorful and inviting, reflecting the artistic spirit of the community. It’s a great place to find unique gifts and support local talent.

The friendly atmosphere and beautiful art make it a delightful stop for art lovers. Whether you’re looking to buy or just appreciate art, the Gallery is a must-see.

Matlacha Community Park
4577 Pine Island Rd NW, Matlacha, FL 33993 | (239) 283-4110

Matlacha Community Park is a lovely spot for outdoor fun. We enjoy the picnic areas and playgrounds, perfect for a family day out. Visitors like the boat ramp and fishing opportunities.

The park also has beautiful views of Matlacha Pass, making it a scenic place to relax. It’s a great spot for kayaking and paddleboarding as well. The park’s facilities are well-maintained, and the atmosphere is welcoming.

It’s an ideal place to enjoy the natural beauty of Pine Island. Whether you’re fishing from the pier, boating, or just picnicking, Matlacha Community Park offers something for everyone.

Lovegrove Gallery & Gardens
4637 Pine Island Rd NW, Matlacha, FL 33993 | (239) 938-5655

Lovegrove Gallery & Gardens is a whimsical art destination in Matlacha. We enjoy the colorful artwork and vibrant garden spaces. Visitors like meeting the artist, Leoma Lovegrove, and seeing her studio.

The gallery is filled with bright, joyful art that reflects the island’s spirit. The gardens are equally enchanting, with quirky sculptures and lush plants. It’s a fun and inspiring place to visit.

The friendly atmosphere and unique art make it a highlight of Pine Island. Whether you’re an art lover or just looking for a cheerful experience, Lovegrove Gallery & Gardens is a must-visit.

Pineland Marina aka Safe Harbor Pineland
13921 Waterfront Dr, Bokeelia, FL 33922 | (239) 283-3593

Pineland Marina, discussed earlier, offers boat rentals, storage, and a full-service fuel dock, making it a one-stop shop for boating enthusiasts. Here is their contact information for your convenience.

Calusa Heritage Trail
13810 Waterfront Dr, Bokeelia, FL 33922 | (239) 283-2157

The Calusa Heritage Trail, discussed earlier, is a fascinating journey through the history of the Calusa Indians. Located at the Randell Research Center, this interpretive trail offers an in-depth look at the ancient civilization that once thrived on Pine Island.

We enjoy walking the well-marked paths that wind through shell mounds and historic sites. Visitors like the informative signs and displays that provide insights into the Calusa’s way of life, their fishing and shellfish gathering techniques, and their complex society.

Guided tours are available for those who want a more detailed understanding. The knowledgeable guides are passionate about sharing the rich heritage of the Calusa people. It’s a unique educational adventure that offers a deep connection to the island’s past.

Capt'n Con's Fish House
8421 Main St, Bokeelia, FL 33922 | (239) 283-4300

Capt'n Con's Fish House, pictured and discussed earlier, is a beloved local seafood restaurant on Pine Island. We enjoy the fresh, delicious seafood dishes and the welcoming, laid-back atmosphere. Visitors like the waterfront location, which offers stunning views of Charlotte Harbor.

The menu features a variety of seafood favorites, including grouper sandwiches, shrimp baskets, and clam chowder. The friendly service and casual vibe make it a great spot for a relaxed meal with family and friends. It’s also a popular place for watching the sunset, adding to its charm.

The restaurant’s rustic decor and nautical theme create a cozy, beachy feel. Whether you’re a local or a visitor, Capt'n Con's Fish House is a must-visit for anyone who loves seafood. The combination of great food, beautiful views, and a friendly atmosphere makes it a standout dining destination on Pine Island.

The Perfect Cup
4548 Pine Island Rd NW, Matlacha, FL 33993 | (239) 283-4447

The Perfect Cup Restaurant, pictured earlier on this page, is a charming eatery known for its delicious breakfast and lunch offerings. We enjoy the cozy, inviting atmosphere and the friendly service. Visitors like the extensive menu, which includes everything from hearty omelets and pancakes to fresh salads and gourmet sandwiches.

The coffee is a highlight, with many guests raving about its rich, smooth flavor. The restaurant’s decor is warm and welcoming, making it a comfortable spot to start your day or enjoy a leisurely meal. The Perfect Cup is popular among locals and visitors alike, thanks to its consistently good food and relaxed vibe.

The staff is attentive and eager to make your dining experience enjoyable. Whether you’re craving a classic breakfast or a tasty lunch, The Perfect Cup delivers with style and flavor. It’s a must-visit for anyone looking to enjoy a great meal in Matlacha.

Low Key Tiki
3135 Stringfellow Rd, St James City, FL 33956 | (239) 282-8454

Here is the contact information for Low Key Tiki, pictured earlier.

Interactive Google Map of Pine Island, Florida

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