As I drove to Captiva on Tuesday, May 21st, my excitement was through the roof! I was about to meet one of the island's most knowledgeable guides, Captain Brian Holloway (Captain Brian on the Water).
Arriving at McCarthy’s Marina, I quickly paid for parking, grabbed my trusty backpack, and headed to the dock. There he was, sitting on his boat, ready to show me the magic of the area he loves so much. His talk began the moment I boarded the boat, and it felt like catching up with an old friend.
The weather was perfect, as it often is in May in Southwest Florida. This time of year, our outer islands are in full bloom, and baby animals are everywhere. Almost immediately, we encountered a small pod of dolphins, including a playful young one splashing its tail, teasing the others. Our next adventure was to Cabbage Key. We navigated to the Gulf, cruising along the stunning beach of North Captiva. This part of Captiva was separated by a hurricane in 1921, creating North Captiva and Redfish Pass. Imagine an island with no cars—only golf carts and bicycles. It’s like stepping back in time!
We then passed by Cayo Costa, another off-grid island, mostly state park land. Moving through Captiva Pass towards Cabbage Key, we marveled at the historic fish houses to the east and the crystal-clear waters of Pine Island Sound. As we rounded the south end of the island, we pulled into the docks, where you can “shower with a friend.” The dockmaster greeted us warmly, sharing stories of the inn, the family, and the prehistoric history of the island. Cabbage Key, the highest point in Lee County, was protected from the surge of Hurricane Ian. This island is a shell mound dating back to 100 BC until the Calusa disappeared in 1570 AD. The current building was constructed in 1936 and has been a beloved spot ever since.
For lunch, there were so many delicious and fresh options. But beware of the Cabbage Creeper cocktail—it will sneak up on you! Don’t forget to hang your dollar bill on the wall, ceiling, or even a post with your best one-liner or autograph. This tradition supports charity! After lunch, we strolled around the island, soaking in the nature, history, and beauty of May in Southwest Florida. We even spent a few moments with a friendly manatee at the dock. A stop in the island gift shop revealed the old ways residents were alerted to incoming hurricanes. You'll have to ask Captain Brian about that—I can’t give away all the secrets!
After our stop, we headed to Cayo Costa for some shelling and exploring. Noticing the tracks of an alligator that Captain Brian estimated to be 4.5-5 feet long, I decided not to venture deeper into the trees. An osprey family watched us, with Mama Osprey making it clear we were a little too close to her young ones. Pulling anchor, Captain Brian took the boat around North Captiva into Safety Harbor, where you can dock and have lunch. Since I was still full from the shrimp salad at Cabbage Key, we did not stop.
It was time to head back to McCarthy’s Marina, as my doggo was waiting at home. The day could have gone on forever! I had an amazing time and discovered that I want to explore more of this beautiful place we call home. I cannot recommend Captain Brian highly enough. His wealth of knowledge, his way of making you feel like family, and his palpable love for Sanibel, Captiva, and the other Lee County outer islands create the perfect recipe for a day of wonder and smiles that you'll remember for years to come.
