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Last summer, I was delighted to be invited to join two of my girlfriends on a sailing trip—my third, no less! This trip would surely herald my promotion from nautical novice to savvy seafaring expert. I was to join them on a charter in Southwest Florida and sail along the Intracoastal Waterway. Many moons ago I had spent some time camping in the Everglades, but this was to be my first venture to Florida’s west coast.

The month was June, not the best time to go to Florida, but the only window in my friends’ hectic schedule. I, therefore, did what all true Brits do when planning a trip—checked the weather forecast. Horrors! I rebooted my weather app four times but to no avail. A muggy 85 degrees F and rain, rain, rain for the entire week. Wall-to-wall rain and I didn’t even own a raincoat.


Pip, a veteran of the waves, and Dawn, another capable seafarer, met up at Boston’s Logan Airport where I found them busy ordering our supplies online to be delivered that afternoon directly to our boat. What a treat! A few hours later, after a short taxi ride from Southwest Florida Airport, we arrived at Tarpon Point Marina, home base of Southwest Florida Yachts.

Our 40ft Fountaine Pajot catamaran, Breathing Room, was well equipped and had a woman’s touch to her. Colorful throws adorned the cabins, and the comfortable memory-foam mattresses and pillows were most welcome.

Following markers and not the charts

We met with Mark from Southwest Florida Yachts, who expertly briefed us on some quiet anchorages and itinerary recommendations. Mark also warned us that, due to shoaling, the channel markers were sometimes moved and did not always correspond exactly with the charts and the GPS. Follow the markers, he told us, not the chart.

In the course of our briefing, we also learned that the controlling depth of the Gulf Coast ICW is 8ft and the mast height restriction is 49ft. Little did I know then how pertinent all this information was going to be. Although the ICW offers no mooring facilities outside the marinas, Captain Pip assured me she could handle an anchor. (Never mind her nightmare tales of a best-forgotten Belize experience involving dragging into mangroves.)

Meanwhile, ominous-looking clouds gathered, and then gathered some more. Finally, the heavens opened in the way only a tropical storm can, a kind of rain we all agreed was too wet even for manatees. Fortunately, Tarpon Point Marina is well-appointed, and we took refuge for the evening in the lively Pinchers Crab Shack. Did we take out their large Key lime pie ($15) for the onboard freezer? Of course, we did—a good move that took care of desserts for the week.

Back on board, we dried our raincoats, made a cup of tea and talked about the weather. We slept soundly, having galvanized ourselves to head off in the morning come rain or shine.

Luckily, the morning shone, and we headed onto the Caloosahatchee River and gingerly approached the narrow pass aptly known as the “Miserable Mile.” Miserable, clearly, for the pain of straying outside of the channel, where the depths on either side suddenly drop to 1ft or less. Our goal was to reach Sanibel Island alive—and preferably not too miserably.

The aptly named Breathing Room was a perfect charter platform

The aptly named Breathing Room was a perfect charter platform

The Elusive Marker 101

My idiot’s tourist map said “Channel Crossing—Navigate with Care,” and I hoped the skipper’s charts were a bit more informative before remembering that Mark had warned us to throw the charts to the wind. It was a question of all eyes on finding the markers. Easier said than done, as we couldn’t find marker 101 anywhere. Then, out of the blue, alongside came a happy-go-lucky little motorboat. Was it offering us help? No, the driver was asking for a us cigarette lighter. “No, we haven’t got one!” we yelled in unison and returned to panicking over the elusive marker 101.

Somehow we stayed in the channel, and with the southern end of Pine Island to starboard and the tip of Sanibel Island to port, we made it across the expansive bay without running aground.

Ding Darling’s Dark Skies

That evening we dropped anchor in Ding Darling National Wildlife Refuge on Sanibel Island. Depths were a pretty consistent 5ft, and we found ourselves the only boat in this well-protected bay. Pip handled the anchor like a pro while I looked on, sweating about mangled digits. Her words, “I might not know where the life jackets are, but I’ve found a box of Band-Aids,” did not fill me with much confidence.

That evening we launched the dinghy and pootled into Tarpon Bay, where we watched hundreds of birds come home to roost off in the distance on the shore. As we were doing so I spotted my first pair of wild pink flamingos, along with many egrets and an osprey. The skies were dark, menacing and mercurial. Back on board after supper, we made a cup of tea, ate frozen Key lime pie and talked about the weather.

We left Sanibel early the next morning to beat the oncoming storm and headed north past Captiva Island to Useppa Island for a pit stop. It was a rainy, sweltering and stormy passage. On arrival, the breaker went on the anchor, and the weather was ominous so we decided to push on to Cayo Costa, anchor there and wait out the oncoming storm.

Weathering the Storm on CayoCosta and Pelican Bay

Mark had warned that the entrance to Pelican Bay was narrow, poorly marked and apt to change with shifting shoals, but we got through with no problems and safely dropped the hook in the island’s delightful horseshoe-shaped, mangrove-lined anchorage. Cayo Costa prides itself as being one of the most beautiful of the barrier islands, a tropical state park that offers excellent shelling, beachcombing, swimming and spectacular sunsets. It certainly is a gem, comprising a 2,426-acre barrier-island reserve, complete with nine miles of white sand beach on the Gulf side.

In Pelican Bay we were joined by dolphins. Dolphins galore! And they almost our only company. Pip had been here before, in May 2017, which is more of a peak season and found two-dozen other boats anchored there. During our visit, however, we were one of only four boats in total. Bliss.

Not too blissful, though. That evening we were eaten alive by bugs, though, they dispersed somewhat after a squall came through. Dark clouds moved majestically around the setting sun—not your typical orange-and-pink Florida sunset, but with a moody and menacing beauty nonetheless. After supper, we made a cup of tea, ate frozen Key lime pie and talked about the weather.

It’s thrilling to be awakened by lashings of rain, thunder and lightning, and lovely to watch the rain dance on the water, especially when you are safe and sound in a secure anchorage. The sound of heavy rain on a boat is like being inside a kettle drum. There was nothing to do other than make a cup of tea, finish off the Key lime pie and enjoy the weather.

Luckily, by now we’d learned that these kinds of Florida storms don’t last long. And when it passed we hopped in the dinghy and headed ashore, in dire need of fresh water, insect repellent and more tea. The island is largely uninhabited except for a ranger station and a handful of camping cabins. There is also a small dock for dinghy tie-up and miles of trails that can be explored on foot or by bicycle. (The latter can be rented for a reasonable fee.) As the weather continued to improve, day-trippers started arriving in numbers. A tram runs hourly to the gulf side. However, we opted for some dinghy action to explore the island’s many nooks and crannies. Alligators were plentiful in the coves. It’s lovely seeing these prehistoric creatures in their natural habitat.

Like three coiled springs we hit open waters

The following morning the weather was bright and clear. Whoo! Like three coiled springs we weighed anchor and made our way around the head of Cayo Costa and out into the Gulf of Mexico. Directly across the bay to the west is the Boca Grande (big mouth) Pass, a commercial shipping channel as well as home to shoals of world-famous tarpon and the hundreds of fishermen who pursue them.

The weather was glorious and brought out many tug boats and pleasure cruisers alike. It looked like a scene from an Alfred Wallace painting, as the waters turned from brown to bright turquoise. Before I knew it, the mainsail and jib were up, and we were riding the waves at 8 knots—a great start to a wonderful day. Buoyed by the kinder weather, we decided to anchor again off Useppa and pay the famous island a visit.

The tropical garden of Useppa Island

Useppa, we found, is special. It has first-class amenities set in a beautiful, lush tropical atmosphere. There’s also plenty to do ashore, whether it’s enjoying a cocktail at the Tarpon Bar, dinner in the historic Collier Inn or a spot of island history at the Barbara Zumwalt Museum. Although it’s a private island, Barb and Vic Hansen from Southwest Florida Yachts are both members, which means their charter customers enjoy full access to this quiet, secluded haven as well.

Interestingly, Useppa is among the more significant historical sites in Florida having been occupied nearly continuously for over 10,000 years. It is also extensively landscaped, so that going for a stroll is like walking through a vast botanical garden with beautifully manicured and tended tropical plants from all corners of the world. Orchids hang from every branch. Palms, bougainvillea, bamboos and banyan trees grow everywhere. If I wasn’t already married, I’d make my honeymoon there. Taking in all the beauty it was incredible to think that as recently as 2004, Hurricane Charley, a category 4 storm, caused $15.4 billion worth of damage to the area, leaving 5 million tons of debris in its wake. (There I am talking about the weather again!)

Red Right Returning back to the marina

From Useppa we decided to head to Sanibel for our last night and ensure a quick stress-free hop back to the marina the following morning. Had the weather not hindered our plans, we would have stopped off at Cabbage Key, the picturesque island made famous by Jimmy Buffett and the inspiration for the song “Cheeseburger in Paradise.” The island’s Dollar Bar is also decorated in a unique kind of wallpaper—dollar bills! Maybe next time, weather permitting, of course.

As fate would have it, we enjoyed an uneventful cruise back to Sanibel, (though we did note the low-lying power cables en route that had apparently only recently taken out another boat’s mast). Especially satisfying was being able to spot all the necessary markers along the way. My mantra was now “red right returning,” the opposite of in England. I had, indeed, learned something new about sailing on this cruise in the United States!

So, to conclude, what’s not to love about sailing in Southwest Florida? Even in June, we had a blast. Pip had a few sleepless nights babysitting the depth alarm, but that’s par for the course when you’re in charge. There wasn’t much swimming, on account of those pesky alligators, persistent rumors of bull sharks and those suspicious-looking brown things floating in the water. (Turns out they are natural mangrove debris. Who knew?) And who cared about the weather? I got to wear my new raincoat, and it gave us all something to talk about. 

Sian Davies is a frequent visitor to the United States. She and her crew chartered with Southwest Florida Yachts. 

March 2020



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