Skip to main content

A Day of Island Hopping: Cruising the Barrier Islands of Pine Island Sound

Apr 20, 2022 08:40AM ● By CAPT. BRIAN HOLAWAY

Friends were in town for the day and wanted to go out on the water. They had me at, “Let’s go do what you want to do.” For me this means following no schedule and just seeing what happens. Some of the best-laid plans are never really made; they just happen. 

We left McCarthy's Marina on Captiva in the morning, talking and catching up as we idled through Roosevelt Channel. The tide was coming in but was still low. Brown pelicans and royal terns stood on the sandbar that marks the entrance to the channel. We picked up speed while continuing our conversation and figuring out how long it had been since my friends were last here.  

The ride to the north end of Captiva went fast. We slowed down in the middle of Redfish Pass and watched ospreys feeding near their nests. The gulf was calmer than the sound so we ran along the beach of North Captiva. We spotted dolphins at the end of the island (a sight that never gets old). I put the engine in neutral and shut it off. You could hear the dolphins take a breath as they came to the surface. We listened and watched until they moved farther out into the gulf. 

Our first destination of the day is one of my favorites, Cayo Costa. This island is more than 90 percent state park and has in excess of eight miles of stunning beach. We anchored at the south end and set out in search of shells. The beauty of the barrier islands is that they are always changing. I had last been to Cayo Costa 48 hours earlier, but now the beach was full of new wonders. We walked and talked and laughed, occasionally bending over to pick up tiny treasures.   

We walked back to the boat, pulled the anchors, and made our way to one of my favorite island lunch destinations, historic Cabbage Key. I was excited to show my friends the island and meet some of the cast of characters that keep it running. We were greeted by the salty dockmaster, Dave Godfrey, as we pulled into the slip by the old dock house. The pace of the island was quiet as we walked up the steps past the frangipani tree to the right and the gopher tortoise burrow to the left.  

The restaurant staff welcomed us with smiles and led us to a table in the back room, which is covered in dollar bills that have been signed and taped to the walls (some estimate $60,000 to $80,000 stuck on these walls). We ordered the smoked mahi fish dip, black beans and rice with the fresh catch of the day, and a cheeseburger. Dessert was a happy surprise: an ice cream sandwich with homemade cookie-dough crust, drizzled with caramel on top. Lunch was a success.  

I had one more stop to make on our way back, an island surprise of sorts. 

We bid farewell to the dockmaster and pointed the boat south. The wind calmed as we made our way across Captiva Pass and into Safety Harbor on North Captiva. We tied up to the dock by the Mainstay restaurant where we could hear blues music coming from the outside bar. I wanted to give my friends one more surprise: a Bloody Mary of epic proportions. Called the Mainstay Mary, it is served with a conch fritter, scallop, shrimp, bacon, pickle, jalapeño, olive, and celery. An hour later there were smiles all around as we got back on the boat. The sounds of the blues slowly faded as we untied the bowline and headed back to Captiva. 

Island hopping is what you make it. High tide, low tide, sunny or cloudy—just get out there and find the island of your choice. It’s waiting for you. 


Capt. Brian Holaway is a Florida Master Naturalist and has been a Southwest Florida shelling and eco-tour guide since 1995. His boat charters visit the islands of Pine Island Sound, including Cayo Costa State Park, Cabbage Key, Pine Island, and North Captiva.