What to do on Estero Island in Fort Myers Beach, FL — Tiny Island, BIG fun

Looking to pack a bunch of fun in just a few short days? Staying in an area with lots of things to do does not necessarily mean you have to stay in a big, densely populated city. Consider maxing out your vacation by staying in an area with short commute times between attractions, Estero Island, located on the Gulf side of Florida offers just that.


How did I decide to explore this thumbnail of an island? I was finishing up a short girl’s trip in Naples, FL, and wanted a few days to myself. This was my first solo vacation, EVER. I have been undergoing a personal transformation since removing alcohol from my life in the fall of 2021 and needed the time in a rejuvenating place that only the energy of the ocean can offer. I had already traveled halfway across the country from the St. Louis area, so why not?!

As a traveler that becomes recharged in nature, I like to look at a Google map of a region and see what natural areas are nearby [parks, conservation sites, botanical gardens, etc.]. I then research those pins and see if there are attractions of interest to me. I check Groupon for deals on adventures and dig deep into vacation rental sites for good locations and tips from local guides. Airbnb does a nice job with the local guides, and they also offer tours/excursions, many run by locals. That research led me to the 6.24-mile-long Estero Island. From Naples, FL I picked up my rental car and headed south.

I decided to visit a few thrift shops because I couldn’t check into my Airbnb in Fort Myers Beach, FL - Estero Island until the late afternoon. Go to thrift stores in Florida, folks. Florida is full of old people. Old people have lots of nice things that are quality-made. Mainly because they bought their nice things before fast fashion became a thing in clothing and home decor products, diminishing the overall quality of goods. Those old people die in Florida or they get to their snowbird nest and realize they don’t have room for all their things. Their nice things make it to an array of thrift and consignment shops.

I’m not going to make specific recommendations because they are literally everywhere and you know how to use Google maps. I got a luxurious sherbet-orange classic cashmere sweater for $3, an early 1990’s oversized American flag knit sweater for $4 (because, Florida), and a badass vintage Japanese coffee mug that was half-price for $0.50. My kind of souvenirs. Then I headed to my tiny island oasis for the weekend.

Estero island has plenty of selections of restaurants and cafes at various price points. I make an effort to patronize hyper-local restaurants, but could not resist the beach front allure of Pinchers. I ordered Gulf harvested oysters, soft shell crab, and an N/A beer. The food and service was excellent. There is something to be said about the consistency a regional restaurant chain can offer by streamlining menus and securing quality vendors. After my dinner, I stepped off the dining deck, walked past some super cute beach pups (lots of cute dogs to look at if that is your thing - there is even an off leash dog beach), and headed towards the ocean to get a feel of the island. There are lots of pretty little shells, so make sure you wear shoes.

After dinner I checked into what can best be described as a “micro-suite.” I immediately thought of how people live in tiny apartments in LA and NYC. Dolphin Inn Resort was built mid-20th century. They have done their best to not make it show. I was on a tight budget for this trip. While the room was tiny, it had everything I needed. Bed, kitchenette, and a private bathroom. I’m not sure I could have stayed there with my burly 6’3” husband, but it was fine for just me. The location was perfect and I had a nice bay view.

THE FIRST NIGHT…

I found myself drawn to the beach through a pathway between some of the larger condominiums on the beachfront. I watched the sunset with the sand in my toes and found myself drawn in by the sound of 90s chill pop music coming from a nearby resort. I followed the notes carried by the ocean breeze.

At first, I sat on a picnic table outside the beachfront entrance to the Outrigger Beach Resort with just a glimmer of pink-glowing sunlight still in the sky, eavesdropping on the Alanis Morissette and Matchbox Twenty tunes played by my fellow millennial. Those songs took me right to 1997 and made me think about where I’m at in life; I cried a bit staring at the last bit of pink in the sky. I decided to patronize the place, bellied up to the sticky Tiki Bar, and ordered myself a virgin pina colada to dry my tears. I sat by a warm gas heater and swayed to Fiona Apple (MY GIRL). I watched some boomers dance and thought of my dad who I recently lost. He would have loved it there, never one to miss an opportunity to dance. I cried a little more, slurped the rest of my sugar bomb, gave the nice musician a $20 tip for my cathartic release triggered by the sounds of my childhood radio dial, and headed to my quaint airbnb to crash.

DAY TWO WAS PACKED…
I went kayaking in the mangroves with Lovers Key Adventures at the Lovers Key State Park. The tour boasts manatee sightings. I did not see any but I did see iridescent jellies - the radiantly beautiful non stinging kind, fat iguanas in the trees, and countless bird species. The tour was relaxing, and the history of the area provided by the knowledgeable tour guides made it even more memorable. There are plenty of places to rent your own kayak in the area, but I like tours so I can learn about what the area is known for. I learned that mangrove forests play a huge part in maintaining the ecosystem for wildlife and human consumption of seafood, amongst other things.

I stopped at the Estero Farmers Market at Miromar Outlets on my way back to my vacation rental for lunch. The market had around 30 vendors. You can find fresh fruit and veggies, boutique foods, artisan crafts and jewelry, baked goods, and more! I picked up a few things for lunch and a local kombucha vendor provided me with the energy boost I needed for the rest of the day! The best part about Florida farmer’s markets? Most are open year-round and you will often find some open mid-week, not just weekends.

That afternoon I Visited the Mound House and learned about the Calusa Indian inhabitants and their 2,000 y/o culture which presided in the region until European settlers came south to the area. Wild story… The family that owned the land began a project to dig out an aging swimming pool. That is when they found the layers of shells/mounds put there by the native inhabitants over thousands of years. The city decided it was worth saving and stepped in to preserve the site. I made sure to get there for one of the guided tours and then explored the grounds myself after the tour. I almost always spring for the guided tour because, who wants to read every sign? The site also has what I will call a “mini botanical garden.” With well-marked plant species dotted throughout the property.

On my way to the Mound house I passed a park I decided to visit later. I found myself back at the Matanzas Pass Preserve. I wanted to spend some time truly immersed in nature. The [mostly] boardwalk style paths at the preserve offered that, being on a smaller island, at the edge of the continent. Virtually no noise; other than passing airplanes and few other visitors.

I spent 2 hours in the mangrove forest. Walking and meditating + releasing some shit from my head and my body. The trail leading to the lookout to the bay provided a different vantage point to the island, away from the sandy beaches. Wear bug spray.

Here is info about the preserve and a trail map.

THE FINAL NIGHT…
As a person living an alcohol-free lifestyle, happy hour and nightlife can seem a little strange. The proprietor of my favorite local coffee shop back home kept talking about kava bars popping up in bigger cities. I decided to seek out a kava bar in FL. Luckily, I found Kava Culture Kava Bar, a scenic 15 minute drive to the mainland. Kava is a root from the South Pacific; exotic and earthy. At many kava bars, this beverage is still made in the traditional way of squeezing the root and drinking from coconut shells. A natural muscle relaxer, kava gives you a natural sense of calm and well being without affecting cognitive or motor skills. Some people say, it will make you feel a little high.

The vibes on this place! The lights were dim, the patrons chatty (appropriately), music was moody in a good way, and the staff warm and welcoming. I found myself taking the initiating “shot” of kava, followed by some delicious “beer-style” carbonated kava, and a turmeric and black pepper latte. I even stumbled across a bookcase with some esoteric books to thumb through while I was bellied up to the bar (which does not serve any alcohol.) I would 10/10 recommend this experience to anyone, drinker or not. Let me be clear, I was not stoned. I was exceptionally relaxed, at peace, and introspective in public - which is unusual if you ask me.

The kava tenders recommended a local taco joint for dinner called Tiki Subs. The name is confusing but the tacos were so yummy + fresh! And crazy affordable. I saw lots of locals pop in and out while I was waiting for my food, which is always a good sign.


Remember when I told you my vacation rental was mid-century built? You want to know how I know? By the authentic olive green bathtub and 1”x1” green and blue speckled, ugly as hell wall tile in the bathroom. I don’t have a bathtub at my house ( a barn built in the early 1900s) and had been craving a bath for months so I decided to make it work.

I pulled out an oil space heater from the closet (safe, I know) got it warmed up in the toilet/tub room (nook), and let the steamy hot water flow into the bath. I made my own sauna. I’m including this antidote to say, I could have been disappointed by the fact that the bathroom in the photos of the rental on the major vacation rental site was inaccurate (my unit’s bathroom was not renovated). I could have gotten down on myself for not being able to afford something nicer. But I made the best of it. We can do this with almost any situation if we choose to look at things in a positive light. I loved my mid-century sauna bath. I slept like a baby that night.

THE FINAL MORNING…

I got up early to see the sunrise. The thing about tides on these smaller islands means you can only access certain areas at certain times of day. Make sure you know where your heading before you venture out (you can search tide maps here). I missed the sunrise, but went for a beach run and a refreshingly chilly dip in the Gulf of Mexico. I left some non-empowering energy behind for the ocean to do with it what she wishes. Thank you Mother Earth.

I went back to my vacation rental to pack up and head out. I drove with my windows down to the Fort Myers Airport (about a 30 minute drive), singing loudly. I learned a few things on my first solo vacation. I can go pee as much as I want without having to consider other parties. Traveling solo makes you incredibly nimble, I packed a bunch of activities into just a few days. I ate and drank what I wanted, when I wanted. I got exactly what I was looking for: deeper connection to myself and nature.

Would you take a solo trip like this? Tell me in the comments!