Estero Island


Imagine waking up at the crack of dawn, making your cup of coffee and walking out to the beach to people watch as the locals walk and stop to pick up a few sea shells here and there. Maybe there’s someone on a paddleboard drifting by quietly. Sitting there enjoying your coffee with no news to watch. No worries about the stock market or whatever controversy is the flavor of the day. You inhale deeply of air that smells like a mix of your coffee and the ocean, and you just watch the day waking up to the sound of waves lapping at the shore.

White sand beaches and a cup of coffee. What else could you need to start your day off relaxed? For the last six years, every year except Covid 2020, myself and a few longtime friends have made our annual pilgrimage to Fort Myers Beach, Florida. Fort Myers Beach is a town located on Estero Island on the gulf side of Florida. It’s not exactly a sleepy, unknown seaside town, but it’s probably as close to anything you can find nowadays, if you go at the right time.

My friends and I go late October/early November every year. It’s not tourist season at that time and it’s definitely not Spring Break. If you go at the right times of year, this place is an absolute gem for relaxing beach time. In the month of November daily high temperatures range from 78°F to 82°F, rarely falling below 71°F or exceeding 87°F. Perfectly comfortable.

In Oct/Nov this is how crowded the beaches are in Fort Myers

If you don’t like just laying around the beach, there’s plenty of other fun activities, like renting a jet ski, going paragliding, fishing or golfing. Like any great beach community there is also a thriving nightlife here with bar/restaurants up and down the beach where you can get a great meal with a view of the ocean before heading inside for a few adult beverages.

Although this place is getting busier and more popular, it still has an awesome, small beach town feel. There’s a couple 7-Eleven’s and one Publix supermarket. The rest of the businesses on the island are local owned mom and pop shop types of places, whether it be restaurants or gift shops.

Where should you stay when you go to Fort Myers Beach? There’s plenty of great options. There’s beach resorts and hotels everywhere and if you’re vacationing on a budget, just pick a nice little hotel across the street from the expensive ones and walk over to the beach through the many public access areas. There’s also a fantastic AirBNB/VRBO community of property owners that will rent you anything from a beachfront house to a condo or a beautiful bungalow on an inter-coastal waterway with a dock. While you’re there, if you don’t want to drive the rental car everywhere, you can also rent golf carts that are street legal just to drive around the island.

There’s a sunset like this almost every single night.

Back to my title; why should you visit as soon as possible? In about two years the massive Margaritaville resort that’s being built will be completed. If you love Margaritaville, great! This is a perfect place for it, but my fear is that this massive tourist resort will cause the island to be constantly and perpetually full of people. I fear that those slow, lazy mornings having coffee on a peaceful beach will be gone forever. I really hope I’m wrong, but just in case, visit Fort Myers Beach while you can. ~Phil