The following article is taken from the November
1998 Issue of Sail Magazine
by Skip Brown
For a group of new-to-Florida Charterers, Pine Island
Sound (squall and all)
was a great place in which to gain confidence and
learn some seamanship.
Gaelen, and Tracy sailing
on the Gulf Of Mexico.
breaks on fishermen
casting their nets in the
shallows behind Useppa Island.
it lacked was a film crew and a voice-over.
We were really and truly a National Geographic
special. Spiky pink bolts crackled sideways,
almost in time with the bowling-alley thunder;
the rain, also horizontal, stung our faces and
frothed the water white; the wind gusts buffeted
our boat, eventually flipping our inflatable
This was the first night of our cruise and our
first time anchoring Windquest III, an Island
Packet 38. Three other SAIL staffers, Gaelen
Phyfe, Aimee Curran, and Tracey Farina, and
I had chartered Windquest from Southwest Florida
Yachts in anticipation of a quiet, relaxing
week in Pine Island Sound. This first night
was a trial by squall, and we passed the test.
Our CQR held as did our Bruce which we lowered
overboard mid-squall. The storm went on its
way after two hours of nail-biting, listening
to NOAA weather, and checking the rode for chafe,
and we knew we could anchor with confidence
a dinghy racer and a transatlantic veteran veteran
(three times on a Swan 47), and I, a sometime
charterer and also a dinghy racer, were nervously
responsible for this charter. The idea of chartering
in Florida in May with two of our coworkers
was appealing, of course, but I'd always chartered
with someone who had more experience than I.
Gaelen knew how to pilot and set an anchor but
had always been able to rely on other people's
knowledge and experience. We hadn't ever been
the ones fully responsible for a boat and crew.
Island Packet 38
Windquest III at anchor.
it turned out, Pine Island Sound was an ideal
cruising ground for gaining confidence. Several
barrier islands protect the sound from the
Gulf of Mexico, minimizing the effects of
winds and waves. The area's anchorages and
marinas are close enough that piloting takes
you where you want to go. And the Intracoastal
Waterway (ICW), which runs the length of the
sound and then cuts into the Caloosahatchee
River on its way across Florida, is an easily
identifiable highway on which to travel.
Windquest drew 5 feet, and because many parts
of Pine Island Sound are considerably shallower
than that, we spent a lot of time on the ICW.
But unlike most U.S. highways, there's a lot
to see and do from the lanes of the Waterway.
Costa, a park and wildlike refuge maintained
by the state of Florida, is probably one of
the most untouched ICW exits in this area. Completely
undeveloped, it's home to myriad species of
birds and trees, as well as dolphins, manatees,
and wild pigs. We anchored on the Gulf side
of Cayo Costa for lunch, a swim and a shell
hunt (though not for keeping) one afternoon;
as we ate sandwiches under the watchful eyes
of a pelican, we imagined a Gilligan's Island-like
either side of Cayo Costa (just down and up
the ICW) are Gasparilla and Captiva islands.
We didn't take time to visit the former, although
we were told the biking is lovely, as is the
gawking at the homes of the rich and famous.
We did sail through Boca Grande Pass and gawk
at the Boca Grande Lighthouse, though. Captiva,
well known to landlubbing vacationers, is
south of Cayo Costa and provides an entirely
different kind of fun. Overlooking both the
Gulf and the sound is South Seas Plantation,
a pricy but comfortable resort with its own
spent a night on the docks at South Seas;
after three days without either showers or
ice cream, we felt it was acceptable to shell
out the $5-plus-per-foot dockage fee.
Of The Waters
Of Southwest Florida.
was here that we docked our 38-foot behemoth
for the first time, I drove, Gaelen scampered
around with the bow and stern lines, Tracey
was Springline Girl, and Aimee stood ready
to hold a fender between the boat and the
pilings. It wasn't pretty, but we didn't break
anything and no one got hurt, so we considered
it a success. We met the South Seas harbormaster,
Jack Counsell, who, upon learning that we
were from Boston, wistfully said, "Ah,
God's country" We knew we'd found a friend.
know that sound you hear when you try to start
your car and nothing happens? It's not really
a sound, I guess, it's more of a silence.
Well, we heard a lot of that on our charter.
The cockpit engine starter worked only some
of the time. Rather than call the charter
company for help (which they would have cheerfully
provided), we decided to deal with this "challenge"
ourselves. When she needed to, Gaelen jumped
the solenoid with a screwdriver, providing
both her resourcefulness and her fearlessness
(not that they were ever much in doubt). Jumping
the solenoid became routine, and it was an
example of a problem that fazed us in the
beginning of the week but didn't at the end.
We had a different experience with the dinghy
outboard. It worked fine, but it was really
heavy, and it had a long way to be lowered.
We eventually worked out a system: Aimee and
I got in the dinghy; Tracey and Gaelen stayed
on the boat. Aimee held the dinghy close to
Windquest's stern while Gaelen and Tracey
lowered the outboard down to me. I guided
and secured it to the dinghy transom. A big
sigh of relief completed the procedure.
we had become pretty speedy at putting the outboard
on the dinghy, we decided midweek to anchor
Windquest south of Useppa Island, a very private
island for the very wealthy. Because it's off
limits to cruisers, we dinghied across the ICW
to Cabbage Key for lunch. The Cabbage Key Inn
Restaurant/Marina is a fun stop for burgers,
beers, or a walk on the nature trail (or all
three, if that doesn't seem incongruous). We
actually had water, salads, and a walk on the
nature trail, but got a feel for the place nonetheless.
American mystery writer Mary Roberts Rinehart,
who published most of her work in the early
twentieth century, visited here and was supposedly
inspired enough by the island to write a few
novels. As we walked the rustling, semi-overgrown
trails, it wasn't too hard to see how Rinehart
could have been moved to literary creation.
author locates an
ICW buoy while Gaelen
takes a turn at the wheel.
is credited by devotees of the mystery genre
as having created the "If I had only known"narrative
device: "If I had only known that Cecil
would be stabbed in the pantry, I would have
discouraged him from indulging in his craving
for cucumber sandwiches in the middle of the
night." Hindsight, as all mystery characters
(and nervous charterers) realize eventually,
is a beautiful thing. If I had only known how
pleasant Pine Island Sound, and how much fun
being responsible for a charter would be, I
would have come much sooner.