Long before roads reached the northern end of Pine Island, life arrived by water.

Mail boats tied to the dock. Fishermen returned with the day’s catch. Travelers stepped ashore after crossing Charlotte Harbor. Supplies, stories and opportunity all came through this small stretch of shoreline.

Over the next century, this property became many things: a post office, a general store, a boarding house and a beloved waterfront restaurant. Through every chapter, one thing never changed.

It brought people together.

Today, that story continues with Bokeelia Pointe.

Not as a replacement for what came before, but as the next chapter in one of Pine Island’s most historic waterfront destinations.

Long before roads reached Pine Island, these waters connected Southwest Florida to the Caribbean.

Beginning in the 1700s, Cuban fishermen regularly sailed north from Havana to fish the rich waters of Pine Island Sound and Charlotte Harbor. Seasonal fishing camps, supply boats and trading vessels transformed these quiet waters into a working maritime network that stretched far beyond the island.

By the late 1800s, commercial fishing had become one of the region’s defining industries. Fish were packed in ice and shipped to markets across Florida and beyond, while docks, fish houses and small waterfront settlements grew along the shoreline.

The northern tip of Pine Island became one of those gateways. Long before automobiles, nearly everyone arrived the same way: by boat.

In 1904, H. W. Martin built a modest waterfront building on this site—one that would become one of the most important places in early Bokeelia.

It wasn’t just a home. Inside were Bokeelia’s first post office and a general store, while a long pier stretched into Charlotte Harbor where boats delivered mail, supplies and passengers.

In the early 1900s, there were few roads and little connection to the mainland. The water was the community’s lifeline, and this property was where that lifeline came ashore.

Residents came here to collect their mail, purchase everyday necessities, welcome arriving visitors and catch up on the latest news from beyond the island.

This wasn’t simply another building in Bokeelia.

It helped build Bokeelia.

The Martin family did more than operate a post office and general store. They welcomed travelers.

Visitors arriving by boat could step onto the dock, collect their mail, purchase supplies and spend the night at the family’s boarding house before continuing their journey. At a time when travel was measured in days instead of hours, this waterfront offered both hospitality and a connection to the outside world.

Life revolved around this property. Fishermen unloaded their boats, neighbors gathered to exchange news and families waited for the arrival of mail and supplies. It was more than a building, it was the heart of a young waterfront community.

In 1906, a small one-room post office was built just west of the store. Historical records show it handled only twelve letters that year, a reminder of how small and remote Bokeelia was in its earliest days. The Martin family continued serving as postmasters until 1922.

In the early days of Bokeelia, the water wasn’t just part of life, it was the only way of life.

Boats carried the mail, delivered supplies, transported fishermen and welcomed visitors from across Charlotte Harbor. Every arrival and every departure passed through this waterfront, making the property’s dock one of the community’s most important gathering places.

More than a century later, that connection to the water still defines this place. The harbor remains its greatest asset, offering the same breathtaking views, boating access and sense of arrival that first made this shoreline the gateway to northern Pine Island.

As Pine Island grew, so did the importance of this waterfront.

Commercial fishermen worked the surrounding waters, boats came and went throughout the day, and the harbor became the center of daily life. Fish, supplies and people all passed through these docks, helping shape the hardworking character that still defines Bokeelia today.

While the businesses on this property changed over the decades, its purpose remained remarkably consistent. It was a place where people gathered, where stories were shared, where livelihoods were built and where life on the water brought the community together.

For more than a century, this shoreline has never simply overlooked the harbor, it has been part of its story.

As Pine Island grew, this historic waterfront property grew with it.

What began as a home, post office, general store and boarding house gradually evolved into one of the island’s favorite gathering places. As the commercial fishing industry flourished, the building became closely connected to the hardworking men and women who made their living on the water. Local accounts recall that, for a time, it even served as a waterfront gathering place for shrimpers before beginning its long history as a restaurant.

The Bokeelia Crab Shack

By at least the 1980s, the property was known as the Bokeelia Crab Shack. It quickly became a favorite among locals, fishermen, boaters and visitors who came for fresh seafood, homemade pies, harbor views and the relaxed charm of Old Florida. Boats tied up at the dock while families gathered inside, continuing a tradition of hospitality that had defined this property for generations.

Capt’n Con’s Fish House

In the mid-1990s, the restaurant entered the chapter most people remember as Capt’n Con’s Fish House. Under the leadership of Luretta Williams-Sims, it became one of Pine Island’s most beloved waterfront restaurants. Birthdays were celebrated here, friendships were built here and countless visitors experienced the beauty of Bokeelia from its dining room overlooking Charlotte Harbor.

While the names changed over the years, the purpose of this place never really did. For more than a century, this waterfront has welcomed people arriving by land and by sea. It has been a place to gather, share stories, celebrate life’s milestones and enjoy the beauty of Pine Island.

The restaurants were simply the latest chapter in a much longer story. A story that began decades earlier when this very shoreline welcomed the community’s first mail boats, travelers and fishermen, and one that now continues with Bokeelia Pointe.

For more than 120 years, this waterfront property stood through changing generations, thriving seasons and countless tropical storms. It served the community as a home, post office, general store, boarding house and restaurant, becoming one of Bokeelia’s most recognizable landmarks.

In September 2022, Hurricane Ian devastated Pine Island and caused significant damage to the historic building. Although the structure remained standing, the road to recovery proved difficult, and years of exposure left the building increasingly vulnerable.

In September 2024, Hurricane Helene brought extensive flooding to the property, causing severe additional damage. Just weeks later, Hurricane Milton struck Southwest Florida, inflicting the final damage that ultimately left the 120-year-old structure beyond repair.

After careful consideration, the difficult decision was made to demolish the building in December 2024. While the structure could no longer be saved, its legacy lives on through the generations of island residents, fishermen, boaters and visitors who passed through its doors and made it part of their lives.

Although the building is gone, the waterfront remains, the history endures and the story of this remarkable place continues with Bokeelia Pointe.

While the historic building is gone, the spirit of this place remains as strong as ever.

The waterfront still welcomes boats into Charlotte Harbor. The views that have inspired generations remain unchanged, and the rich history of fishermen, travelers, merchants, restaurateurs and island families continues to define this remarkable property.

With that history comes a responsibility. Bokeelia Pointe is not about replacing what once stood here. It is about honoring the past, preserving the legacy of this waterfront and ensuring its story continues for generations to come.

The building may be gone, but the place, the memories and the history remain.

Every generation has left its mark on this waterfront. From the first post office and general store to the boarding house, the restaurants and the generations of memories created along the harbor, this property has always been a place where people came together.

Bokeelia Pointe is the next chapter in that story.

Inspired by the property’s rich history, Bokeelia Pointe is being thoughtfully designed to honor the character of Pine Island while creating a vibrant waterfront destination for generations to come. It will once again be a place where residents, visitors and boaters gather to experience the beauty of Charlotte Harbor and the timeless spirit of Old Florida.

Just as this property once connected the community through commerce, hospitality and shared experiences, Bokeelia Pointe will continue that tradition in a new way. New homes, restaurants, shops, public spaces and waterfront experiences will bring new life to this historic shoreline while respecting the legacy that came before it.

History is not something to be replaced.

It is something to be carried forward.

That is the vision for Bokeelia Pointe.

Some developments begin with an empty piece of land.

Bokeelia Pointe begins with more than a century of history.

For generations, this waterfront has connected people to the harbor, welcomed travelers, supported hardworking fishermen, celebrated family traditions and served as the heart of a growing community. While the buildings and businesses have changed over time, the spirit of this place has remained remarkably constant.

That spirit is what Bokeelia Pointe is built to preserve.

This is not about recreating the past. It is about respecting it, learning from it and carrying it forward for future generations to enjoy.

While buildings may come and go, truly special places endure.

Bokeelia Pointe

A New Chapter on Historic Ground

History tells us what happened

Legends remind us why places capture our imagination.

If you enjoyed learning about the history of this remarkable waterfront, you will also enjoy The Legend of Bocilla, a romantic tale written by local author Jim Griffiths publisher of Nautical Mile Magazine, inspired by the beauty, mystery, and maritime spirit of these waters

Read the complete story at Nautical Mile Magazine.