Our bareboat charter in southwest Florida had crept up on me, and though I had a fair idea of what awaited us. I had not spent much time researching our destination or potential itineraries in depth. My crew had expressed a desire to spend as much time as possible “off the grid” and were excited about seeking out wildlife. Where could this be found?

The wonders of Amazon Prime provided a cruising guide the day before departure, which I cracked open on the plane ride from Boston to Fort Myers. As I leafed through the guide it became crystal clear that there was a distinct lack of mooring fields in the area. I was going to have to bone up on my anchoring skills. Distant memories of dragging into mangroves in Belize in the middle of the night haunted me for the rest of the flight.

We were five 50-something women—myself, Jean, Leanne, Birdie and Michelle—with varying degrees of sailing experience, but all comfortable on the water and game for adventure. Birdie’s nickname on previous trips was “Dora the Explorer” and true to form she had arrived before us, located our Leopard 38 catamaran, Southern Comfort, scoped out the bars and restaurants, and located the perfect spot for a late lunch where they served alligator bites (a first for me) which we washed down with delicious margaritas.

List in hand, Birdie headed off to the grocery store while the rest of us headed to the boat where we were met with a warm welcome from Southwest Florida Yacht Charters. Mark gave us a thorough boat briefing and recommendations for quiet anchorages. Although I’ve chartered on Florida’s east coast, my knowledge of sailing in the southwest was limited to what I’d learned that morning from the cruising guide, so the local knowledge from Mark proved invaluable. After a flurry of activity, provisions were stored, bunks assigned and we spent the evening relaxing aboard and pouring over the charts to decide on possible itineraries. Between a multitude of quiet anchorages, and marinas aplenty it was going to be tough to choose.

A leisurely start to our first full day meant we did not leave the dock before noon. We crept out of Cape Coral directly into the Caloosahatchee River, part of the Intracoastal Waterway, on a beautiful Sunday afternoon to be greeted by a throng of power boaters. We carefully followed the markers into San Carlos Bay and through a narrow pass called the Miserable Mile, presumably for the misery that results from straying out of the channel, where depths on either side suddenly drop to 1ft or less. With the southern end of Pine Island to starboard and the tip of Sanibel Island to port we followed the ICW across the expansive bay, where we caught a first glimpse of the many dolphins we would see that week, and headed for our first stop in Ding Darling Bay, part of the Ding Darling Wildlife Refuge.

Depths were a pretty consistent 5ft and we were the only boat in this well-protected bay, so all we had to worry about was was deciding on the backdrop we would like for the sunset and drop the hook.

We found our spot and I gave the signal to drop the anchor. An eerie silence was followed by confused looks from the crew as it became apparent that the windlass was not working. We checked the breaker—still nothing. The wiring down below looked sound, so Leanne aka “McGyver” leapt into action with a roll of electrical tape. She loleaped a loose connection at the wiring into the control switch and we were back in business. The anchor dug into the sandy bottom immediately, but given my apprehension about anchoring and our proximity to mangroves, we let out a healthy amount of chain. Leanne set up the anchor alarm, and once my paranoia about dragging subsided we were excited to take the dinghy through the mangroves into Tarpon Bay.

As the light faded we enjoyed watching egrets, pelicans and ospreys going about their afternoon routines, and walked through mudflats to discover a conch nursery of epic proportions. A tired, happy crew returned to the boat for sundowners and Bananagrams. Over dinner, we decided that the following day we would head north into Pine Island Sound and through Redfish Pass, between Captiva and North Captiva islands, into the Gulf, where we would go for a sail and see where we ended up. With so many anchorages to choose from at the northern end of Pine Island Sound and beyond to Gasparilla Sound and Charlotte Harbor (the distances between them relatively small), we felt no need to stick to a set itinerary.

Rested and raring to go after a mangrove-free night, we headed back into the ICW. Mark had warned us that due to shoaling, the markers were sometimes moved and did not always correspond exactly with the charts and GPS, and told us to follow the markers, not the chart. Our passage through Redfish Pass highlighted this. As we carefully followed the markers towards the pass there was a yacht on our port side that was being salvaged; a strong reminder to follow the markers and stay in the channel. As we rounded the northernmost point of Captiva into the pass we were faced with a large swell, and markers that were not even close to where they should have been according to the paper chart and the plotter, but we were committed. There was no room to turn around. Thankfully, a local on a jet ski who was probably familiar with the look of horror on skippers’ faces came alongside and offered to lead us through the channel. Ignoring the charts and GPS, we gingerly motored out of the flat, muddy dark waters of Pine Island Sound into the rolling, crystal-clear blue waters of the Gulf of Mexico.

We had a lively sail in a 15-knot breeze, heading north along the west side of North Captiva Island and Cayo Costa. Giving the Johnson Shoals a wide berth we followed the well-marked channel to the Boca Grande Pass, where we wove a path through a multitude of small fishing boats participating in the internationally renowned “World’s Richest Tarpon Fishing Tournament,” hosted by the Boca Grande Chamber of Commerce and aptly named, as entry fees are $5,000 with $80,000 of prize money at stake. The clear line where the light waters of the Gulf meet the dark waters of Charlotte Harbor provides a unique environment that creates a rich feeding ground, attracting tarpon that can be as long as 8ft and weigh as much as 280lb.

Once through the pass, we headed a couple of markers south on the ICW to Pelican Bay on the north end of Cayo Costa Island. The cruising guide warned that the entrance to Pelican Bay was narrow, poorly marked and apt to change with shifting shoals as winter storms moved through the area. In calm, flat waters we felt confident that with a slow, steady approach and a sandy bottom, we would be fine. As we contemplated our approach, a 40ft cruising boat steamed past us toward the entrance; knowing that they drew way more than our catamaran, I did not hesitate to tuck in a safe distance behind and follow him in. We were greeted by a pod of dolphins and found the perfect spot to drop the anchor in this totally protected natural harbor. Again the anchor set firm on the first attempt and after a swim, it was time for sundowners and Bananagrams again. As we looked back to the harbor entrance we saw a monohull that had clearly run aground; given that it was a rising tide, his pride probably sustained more damage than his keel as he waited to float off the sandbar.

The following morning our meditation on the trampoline was rudely interrupted by the sound of a dolphin coming up for air directly beneath us, which set the tone for the day—it was all about close encounters of the wild kind.

Cayo Costa is a part of Florida State Parks and at 2,420 acres it’s one of Florida’s largest unspoiled barrier islands. It is largely uninhabited except for the rangers station and 12 camping cabins. There is a small dock for dinghy tie-up, and miles of trails that can be explored on foot or by bicycle which can be rented for a reasonable fee. We hiked across the island to the Gulf side to discover miles of unspoiled white-sand beach littered with an enormous variety of shells. The crew were in heaven and spent hours beachcombing and relaxing, watching the plovers running in and out of the surf.

One of the rangers had recommended exploring the mangroves and checking out Manatee Lagoon. Ready for another adventure, we hopped in the dinghy and crept along the mangroves until we found the tiny entrance and quietly puttered through as it opened up into a sun-drenched lagoon. The promised manatees remained elusive, but we were entertained by fish jumping, ospreys sunning and pelicans diving, plus stingrays and an alligator basking in the mangroves. A trio of dolphins escorted us back to Southern Comfort for, yes, sundowners and Banangrams.

The next morning we carefully retraced our steps through the narrow entrance and went for another delightful sail in the Gulf. We were running low on ice and decided to overnight at Jack Point, another sheltered, shallow bay with excellent holding. In stark contrast to Pelican Bay, our view included waterside mansions and a highly manicured golf course. Ashore, we dodged the golf carts to explore the main street lined with boutiques and were invited for cocktails at the Pink Elephant by our neighbors in the bay, the crew of a sailing school boat. On the dinghy ride back to the boat there were screams of delight as Leanne spotted our first manatees—a family of them.

The following morning there was not a breath of wind, so we decided to motor down and explore the islands at the north end of Pine Island Sound—Cabbage Key, the home of the original “cheeseburger in paradise,” Useppa, a privately owned resort, and Patricio Island, renowned for its birdlife. After a lunch stop at Patricio Island, we were eager to head back to Cayo Costa and rent paddleboards. An amazing afternoon exploring the mangroves ended with a magical dolphin encounter as they came alongside the boards to greet us. Exhilarated, the crew returned to the boat for—you guessed it—sundowners and Bananagrams.

I had been noticing throughout the week that we seemed to be the only folks swimming off the boat. Typically there are two reasons for avoiding swimming in an anchorage; poop and sharks. The holding tank regulations are strict and pump-out boats and stations are readily available throughout the area, so I was guessing it was not poop. Birdie’s sister, who lives in the area, had given dire warnings not to swim, fearing we would be attacked by bull sharks. But Mark had reassured me that the bull sharks hang out on the Gulf side, where they hunt tarpon, and that we would be fine swimming off the boat. We had been taking sensible precautions; not swimming at night, nor close to the mangroves where alligators lurk in the brackish waters. On the final morning Leanne was up early enjoying her coffee when she saw an 8ft alligator purposefully swimming across the bay—so apparently they will swim in salt water. I’m glad I was blissfully unaware of this!

And then, all too quickly, our week came to an end. And what a week it was. Southwest Florida offers something for everyone; if like us, you are searching for peace and quiet off the grid, the selection of quiet anchorages seems endless. If you prefer shore-based amenities, there are many marinas offering access to fabulous restaurants. As for the hardcore sailors, there is always the option of heading from the dark waters of the ICW to the lighter waters of the Gulf of Mexico where we found awesome sailing conditions. 

Veteran charterer Pip Hurn sails out of Marblehead, Massachusetts.

MHS Fall 2017