Florida has it’s Emerald Coast, Treasure Coast, and Space Coast. Tampa’s deranged author, Tim Dorsey, calls Florida’s southwest between Sarasota and Marco Island, the Retirement Coast.  We left Twin Dolphin Marina in Bradenton on a sunny morning in early March, bound for this mecca of sand, water, and aging baby boomers.

The Manatee River flows into lower Tampa Bay after passing between the DeSoto National Memorial and Emerson Point Preserve.  Hernando de Soto landed here in 1539, likely by accident since shoals line a very narrow channel flowing out around the point.  Just before Tampa Bay discharges into the Gulf of Mexico, the Southbound ICW re-forms in a channel tucked behind Anna Maria Island.  Southbound through Anna Maria Sound, under a few drawbridges, then into Sarasota Bay, the waters get clearer with each passing mile. We were bound for Venice FL, the first stop on our planned three day voyage to Fort Myers.

Sarasota is a long way from Galveston!

It felt good to be on the water again!  We blocked the cool easterlies by winging the port pilothouse door, opening the leeward door wide to take in the beautiful water and watch our frequent dolphin escorts.  Not until crossing Sarasota Bay and passing the city itself do the shorelines draw close enough to gawk at the homes lining the banks.  Then, rounding Sarasota pass and entering Roberts Bay, the white sand bottom and crystal clear water made our jaws drop.  The cruising grounds behind Siesta Key are the most beautiful we have seen. The beauty continued for two hours, through connecting bays and channels, all the way into Venice.

A pretty Krogen Express adjacent to the Dockside Grill in Venice, FL  

Venice was a perfect stop for a captain still recovering from the Bradenton Blues. The marina was quiet, small, and friendly.  We enjoyed beer and fish & chips from the bar at the stellar Dockside Grill, directly adjacent to the marina. Afterwards, we sipped drinks on the flybridge, enjoying the spectacle of retirees also cocktailing, watching the sunset from the decks of mobile homes lining the waterfront.  A gay live-aboard couple named Bob(s) almost convinced us to stay an extra day, encouraging us to see the town, but we pushed off early the next morning, undoubtedly saving significant further expense at the Dockside.

Two quick bridge openings started our day, followed by a long stretch of canal lined by bike trails teeming with retirees.  Walking, jogging, biking and blading, they were out en- masse.  Further south, the bay widens but is only a couple feet deep outside the marked channel.  Mainland runoff from inland waterways named after alligators cloud the water and silt the bottom – lost is the aquamarine blue that mesmerized us the day before.  Between the inlets that occasionally break through the barrier islands, the incoming tides from the Gulf alternately pushed and pulled Cirila, like a marble on a teeter-totter.

A wee cottage for the 1%

We passed under the Boca Grand Causeway, connecting Gasparilla Island and the town of Placida on the mainland, and entered Gasparilla Sound.  With the wealth of Boca Grande on our right, and uninhabited wetlands on our left, the waters changed color again and we entered Charlotte Harbor.  Because Charlotte Harbor is big, beautiful, and provides consistent depths of ten feet or more sailboats become more abundant.  It indeed feels like big water, offering no clue that just inshore, millions of retirees are driving custom golf carts around 500 acre trailer parks, drinking margaritas and smoking cigars.

We crossed the mouth of Charlotte Harbor early in the afternoon, with original plans to spend the night at anchor in Pelican Bay, adjacent to Cayo Costa State Park. It was highly recommended by our friends on Pegasus and the Bob(s) in Venice.  But because we made good time and winds were expected to increase in the coming days, we decided to press on all the way to Fort Myers, and not risk fouling up the cruise by running aground in the shallow approach to the bay.  Other potential anchorages off Useppa Island and Cabbage Key were tempting but not dog friendly, so we pressed on.  Interestingly, Useppa is a now a privately owned retreat, the pristine white cottages lining its banks hiding the fact that it is a hurricane magnet and in 1960, was once the CIA’s training ground for the Bay of Pigs invasion.  The Bar and Grill on Cabbage Key, just opposite the channel from Useppa, is said to have inspired Jimmy Buffett’s “Cheeseburger in Paradise”.  This area is definitely ripe for further exploration on another visit.

Just beyond lies Pine Island Sound, separating the sparsely populated Pine Island near the mainland, from the barrier islands Captiva and Sanibel. At seven knots, it seemed to take forever to transit this Sound, bringing back memories of those last few hours in the car on a childhood beach vacation.  Finally, our heading veered east and passed the Ding Darling National Wildlife refuge on Sanibel.  Here, the navigation channels became increasingly narrow and complex in the boaters paradise (or hell) approaching Cape Coral and Fort Myers.  Near the mouth of the Caloosahatchee River, boaters compete for lack of etiquette awards in a dredged channel fifty feet wide, aptly named the “Miserable Mile”. Anything from twenty foot pontoon boats to seventy foot sport fishers run this stretch three and four abreast, at speed.  We’re sure much beer has been spilled here.

Taking in another sunset from the sky hammock in Fort Myers

We bounced on through the mayhem of wakes and entered the Caloosahatchee, and as rivers do, the water darkened.  After traveling another hour upstream, past the Thomas Edison and Henry Ford winter estates, we finally entered the City of Fort Myers Yacht basin.  We tied up in slip H1, cracked open our traditional arrival beer, and took stock of what we expected to be our home port for the month of March.