For me, late summer has always been a special time on the water. I enjoy the calm, warm water, the quieter beaches, and the less crowded boat ramps.

It always reminds me that time is running out for one last quick weekend getaway before the kids are back in school and our winter residents begin returning to Southwest Florida.

If someone asked me where I'd spend that weekend, these are a few of the places that have meant the most to me over the years. Some are close to home, a couple are a little farther away, but each reminds me why I've spent a lifetime on Florida's waters.

Cabbage Key

If you've never visited Cabbage Key, it's well worth the trip. Arriving by boat is part of the experience, and whether you're stopping for lunch, spending the afternoon exploring, or staying overnight in one of the island's charming rental cottages, it offers a memorable taste of Old Florida.

Long before today's inn welcomed visitors, the island was home to the Calusa. The historic inn, built in the late 1930s, sits atop an ancient Calusa shell mound that has overlooked Pine Island Sound for centuries.

I've been stopping at Cabbage Key for as long as I can remember. As a kid, we'd occasionally tie up after a morning of trout fishing and head up the hill for a cheeseburger. Later, during tarpon season, it became a favorite late afternoon stop for a cold drink before heading back home. A few years ago, I had the chance to take my mother by boat from Boca Grande for Mother's Day lunch. It's one of those memories I'll always treasure.

Tarpon Lodge

Nestled along the shores of Pine Island Sound in the historic fishing village of Pineland, Tarpon Lodge is one of Southwest Florida's true Old Florida treasures. Originally built in 1926, the lodge has welcomed visitors for nearly a century and continues to offer the relaxed waterfront charm that has drawn generations of travelers.

Whether you're stopping for lunch on the porch, enjoying dinner overlooking Pine Island Sound toward the Gulf, or spending a few nights in one of the lodge's comfortable guest rooms, it's easy to understand why so many people return year after year.

Just across the road, you'll find the Calusa Heritage Trail at the Randell Research Center. The self-guided trail is currently open and offers visitors an opportunity to explore one of Florida's most significant Calusa archaeological sites while learning about the people who lived along these shores centuries before the arrival of European settlers.

Please note that the classroom and visitor facilities remain closed during ongoing construction.

This is a place I'd recommend to anyone looking to experience a little of Old Florida.

Little Gasparilla Island

If someone asked me where they could still experience the Florida I grew up with, Little Gasparilla Island would be near the top of my list.

One of my earliest memories of Little Gasparilla Island goes back to my childhood. I remember looking out over Placida Harbor from my grandparents' home as a handful of lights from Little Gasparilla Island reflected across the calm evening water. Even then, I knew there was something special about this place. It wasn't just where I grew up. In many ways, it became part of who I am.

Over the years, more homes have been built and the lights across the harbor have gradually increased. Yet somehow, Little Gasparilla Island has managed to hold onto the Old Florida lifestyle that first captured my imagination as a child. It's still a place where life moves a little slower, where arriving by boat is part of the experience, and where the natural beauty of the island continues to define it.

With no bridge, no cars, and miles of uncrowded Gulf beach, the island offers something that's becoming increasingly rare along Florida's Gulf Coast—an opportunity to disconnect from the schedule and reconnect with the outdoors.

Homosassa Springs

If you're willing to drive a little farther north, Homosassa Springs has long been one of my favorite weekend getaways. I've always enjoyed places where the water is the main attraction, and Homosassa is one of those places I never get tired of visiting.

The crystal-clear springs are certainly worth the trip, but what keeps bringing me back is the boating. Running the Homosassa River on plane as it winds through the marsh before opening into the Gulf is one of my favorite boat rides anywhere in Florida, especially during the late afternoon and early evening after most of the boats have returned home from a day on the water.

The fishing is another reason I keep coming back. Whether you're fishing the river or the nearby Gulf waters, there's always the possibility of creating a memory that lasts a lifetime.

I remember one trip when a friend and his son were fishing near the mouth of the river late one evening. His son hooked and landed a small tarpon, and seeing the excitement on his face was the highlight of the entire trip. Moments like that are what keep bringing me back.

Then there's scalloping. For me, it's one of the best ways to spend a summer day with family and friends. There's something special about anchoring over the grass flats, slipping into the clear water with a mask and snorkel, and spending the day gathering scallops before heading back to the dock.

Whether you're exploring the springs, running the river, fishing the Gulf, or enjoying a day of scalloping, Homosassa is one of those places that reminds me why I've spent a lifetime on Florida's waters.

Sunset Beach Hideaway – Upper Keys

The last stop on my list is a little farther from Southwest Florida, but it's a place that has become very special to my family. Sunset Beach Hideaway in the Upper Keys has long been one of my favorite places to relax and spend time on the water.

What I enjoy most is that it still feels like the Florida Keys I remember. The beautifully landscaped grounds, private beach, and laid-back atmosphere make it easy to leave the schedule behind and simply enjoy being outdoors. Whether it's an early morning coffee on the beach, a day on the boat, or watching another spectacular Keys sunset, it's the kind of place where great family memories are made.

One thing that makes Sunset Beach Hideaway unique is that, unlike many private vacation homes in the Keys that can only be rented by the month, the property's zoning allows shorter stays with just a three-night minimum. That makes it a perfect long weekend getaway without committing to an entire month.

Whether we're spending the day on the water, exploring the nearby Keys, or simply enjoying a quiet evening on the beach, it's one place I always look forward to returning.

Disclosure: Sunset Beach Hideaway is a family-owned vacation property that my family enjoys throughout the year.

Looking Ahead

I hope you find time for one last weekend on the water before another Florida summer slips away. Maybe you'll revisit an old favorite, or perhaps you'll discover a place that becomes part of your own family's story. That's what these places have become for me, and it's why I wanted to share them with you.

Next Month in The Waterfront Advantage

Waterfront & Island Insight #002

September marks the peak of hurricane season along Florida's Gulf Coast. I'll share a few lessons learned over a lifetime on Florida's waters and some practical ideas that can help boaters and waterfront homeowners prepare.