Gunkholing the barrier islands off Florida's West Coast provides a much-needed winter break

Dolphin at three o'clock! Despite a bout with crummy weather and the reality that our extended cruising weekend was about to end, the crew's attention shifted in unison to the starboard rail and a pod of fins almost within arm's reach. After three days adjusting to the winter whims of Mother Nature in southwest Florida, the universal appeal of playful and curious dolphin still captivated everyone aboard Shamrock, our chartered 40-foot Jeanneau.

Like many sailing adventures, this one began with a surprise and each hour and each day that followed added another flavor to the cruising buffet-sort of a like cooking from scratch and modifying the ingredients along the way. The dolphin encounter as we approached the end of the gunkholding trip was the final touch of spice.

The menu was simple enough: gather some friends and work associates for a mid-December cruise from Charlotte Harbor to the protected waters along the Intracoastal Waterway to the south. Our starting point was the Burnt Store Marina and Country Club, home of the Southwest Florida Yachts sailing fleet. The modern, full-service marina is tucked deep inside the gated community and provides immediate access to Charlotte Harbor and easy access to the Intracoastal Waterway, coastal West Florida, and the Gulf of Mexico.

It would be hard to imagine a more boater-friendly starting point with so many destination options within three hours sailing time from the marina docks. By land, the resort is situated in an undeveloped rural area 30 minutes south of Punta Gorda. When I queried cruising guide author Claiborne Young about the region, his answer was unqualified: "If I had to pick only one portion of the Western Florida coastline to cruise, it would be the Charlotte Harbor-Pine Island Sound region. You could spend months and not exhaust all them any varied cruising possibilities."

Knowing the potential for winter cold fronts and the accompanying north winds, our plans and destinations for the weekend were as changeable as the weather reports. But we were not prepared for the tornado warning that greeted us as we loading provisions and gear. Someone at the Norman, Oklahoma, tornado center had issued the warning for much of our coastal region until noon so we leisurely stowed our gear as I went through the boat layout, head protocol and safety gear with the rest of the crew. The afternoon forecast called for clearing and cool.

Our crew of six included three experienced sailors-myself, my wife Christine Svenson and photographer Walter Cooper. Our friend Suzanne Stierle had been on a powerboat once and Vince and Heather Camarada have spent plenty of time on small fishing boats but neither had any sailing experience. The novice sailors soon discovered Lesson No.1- marine weather reports are just as unreliable as the local television weathermen. The skies cleared briefly, only to be followed by heavy rain with an occasional teasing lull.

We decided to postpone the first day's onboard lunch and sail to Cabbage Key for a hot meal and tour of the somewhat famous destination. Like any number of other cruising hangouts in the tropics, Cabbage Key claims to be the home of Jimmy Buffett's "Cheeseburger in Paradise" lyrics. Whether the claim is truth or fiction, Cabbage Key's location, history and rustic ambiance make it the perfect first stop.

The navigation from the Southwest Florida Yachts docks to open water is straightforward. The main channel within Burnt Store Marina has narrowed as the marina expanded in recent months but there is ample maneuvering room for boats under power. We motored outside the seawalls in an east-west channel through the mangroves and shallows to deeper water. The depths in the central parts of Charlotte Harbor are about 12 feet and we quickly turned to the southwest, rolled out the job, and sailed close-hauled toward the ICW.

While the weather didn't invite bathing suits and T-shirts, it did provide wind to sail through the dripping skies. The bimini offered some protection but this was still a foulies kind of day.

Lesson No.2 (good for novices and old salts alike) was to get local knowledge whenever possible and never totally trust the charts-paper or electronic. Our approach tot he ICW brought us past the well-established and weather-work tripod day-marker 96. It did not appear on any of the charts aboard Shamrock nor on the newly published Chart Kit I brought along. Unlit, it would present a formidable hazard for the inattentive skipper day or night. Mark Winkel of Southwest Florida Yachts had given me a heads-up on the turn into the ICW at the north end of Cayo Costa because discrepancies have been found on electronic charts for this region.

Turning south on to the ICW, we eased the sails to a broad reach with Cayo Costa, a largely undeveloped island state park, on our starboard beam and clusters of mangrove isles and Useppa Island off to port. Two miles to the south, Cabbage Key would be welcomed reprieve from the cool breeze and soggy skies. With little traffic on the often-narrow waterway, we were able to sail deep downwind wing-on-wing then jibe as the channel shifted. We furled the jib as the Cabbage Key Inn and small marina came abeam, and spun the boat into the wind, fired up the diesel, and dropped the main into the self stacking lazyjacks. With dolphins playing in the shallows in every direction, Shamrock glided down the channel. And, as if on cue, the rain stopped. Mother Nature can be a sweetheart.

Like many of the islands and keys in this part of southwest Florida, Cabbage Key has a history of indigenous peoples that preceded the Spanish conquistadors of the 16th century by hundreds, if not thousands, of years. The modern history includes the Cabbage Key Inn, first planned in 1929 as a residence and opened a dozen years later as an inn. That was our destination for lunch and some time ashore to stretch the sealegs.

The traditional broad country porch opened into a small drinking room- bar if you prefer- which led to one of several dining rooms. At first glance the rooms seemed cluttered and unmemorable. But as our eyes adjusted to the softer lighting, the walls and ceilings came alive with money- dollar bills.

There were layers of dollar bills on vertical posts. There were so many layers the posts felt spongy to the touch. Unknown layers covered every inch of ceiling and wall space. The manager on duty suggested there is some $60,000 stuck to the building in some way or another, and each bill was signed by the visitor. The manager Tim Jacobson went on to say that as the bills came floating down due to old age or fatigue they were donated to local charities.

After a tasty meal, including a few of the obligator cheeseburgers, we paid the tab and left the inn without adding any new wallpaper additions but with a bevy of true stories- some believable, some not- courtesy of Jacobson's friendly nature and impromptu tour.

He encouraged our group to climb the water tower for a better look at the lad and seascape. The top of the tower was occupied by a nesting osprey with young and we treaded lightly up and down the time-worn wooden staircase. A tour of the island's nature trail was not practical in the damp conditions but Jacobson added another tale to our whimsical memories of Cabbage Key, a tale about being chased by a galloping tortoise. With the rain still in abeyance, we retreated to Shamrock to plan our voyage back up the ICW a mile or so north to Useppa Island.

Claiborne Young's Cruising Guide to Western Florida has to be the primer for anyone cruising this region and his mix of history with local knowledge is unbeatable. However, Young's description of the privately owned Useppa Island Club and all their charterers are eligible to visit. Visiting boaters who do not have the privileges may be able to visit the island ad use the facilities as prospective members by contacting Useppa Island Club harbormaster

Cozy Useppa Island, less than a mile long, has only a handful of year-round residents but the 100 or so residences fill up through the winter and spring. Golf carts prevail on the paths and the only access from the mainland is by boat. The island also forms a well-protected anchorage in the lee of the southwest shoreline.

The island's Barbara L. Sumwalt Museum fits the island's laid-back ambiance. The historical museum is only open two hours each day and an audio walking tour with a recorded docent emphasizes the highlights of the displays and artifacts. We heard how an uninhabited Useppa was landbound until after the Paleo-Indian era 10,000 years ago and it didn't become an island until 4000 B.C. earlier.

Perhaps the island's least known historical context is the role it played in the Bay of Pigs invasion. Useppa was one of several South Florida locations where the CIA trained paramilitary forces that attempted to overthrow the Cuban government in 1961. The museum is a treasure all to itself, and with the $3 admission donation, the experience was, as they say, priceless.

Dinner ashore at the Collier Inn was our splurge for this cruise and the casual dining area was appropriate for this crew's wardrobe. With drinks, the meals were about $40 per person. A formal dining room was available for those who cruise with evening dresses, dinner jackets and neckties.

With the bow into the wind and Shamrock tied smartly to the visitors' dock, sleep came easy. The long day had included a tornado warning and rain but it also included visits to two memorable islands, some historical surprises, and an evening recalling the experiences and galloping tortoise story with friends.

Since we had decided to wait for the museum to open at noon, our troupe split up the next morning in search of whatever we found. Walter's photographic instincts were working overtime on this fantasy island. The rest of us toured the walkways, checked out the huge croquet court, walked the beaches, and imagined what it would be like to live there. It might be too quiet for some, too expensive for most. But sailors are dreamers and Useppa Island could spark some pretty fanciful dreams.

By this time I was wondering who had dreamed up the weather forecasts. Mother Nature wasn't cooperating as the north winds turned colder. Our first choice for an overnight anchorage, Point Blanco, wasn't accessible due to the strong winds and a falling tide. No problem, mon. We're on island time.

The southern end of Cayo Costa, just inside Captiva Pass, became our second choice and getting there was another easy downwind sail in the ICW with the north breeze blowing. With Cayo Costa's pristine shoreline 100 yards off the port beam and a turbulent and impassible Captive Pass off the stern, we set the Delta anchor in the muddy sand. It was popcorn and cocktail time.

Wind on a sailboat can always be a mixed blessing. Under sail, it can help or hinder progress to the destination. At anchor, it can keep the bow straight against a contrary current. And the stiff breeze sweeping over the deck of Shamrock sure got the barbecue grill glowing in short order. This well-stocked expedition hadn't scrimped when provisioning and the evening menu of bacon-wrapped filets, fresh jumbo shrimp, salad, and warm bread disappeared almost as quickly as it had been prepared. The abundance of food, hiking at Useppa, and cold breeze took its toll and the crew sought out their berths early.

Having watched the boat "search" at anchor in the building breeze for several hours with no signs of dragging, I was confident we'd be in the same spot when the sun came up. Lesson No. 3 on this trip, and it's relevant for many situations (including reefing), was to deal with a potential problem when you first think about. If you're thinking about reefing, it's very likely time to reef. In our case, the main halyard was banging and the anchor chain clanked a bit each time and the boat reached the end of its searching arc. I should have fixed it before heading into the forepeak berth for the night but I didn't. The noise level rose and fell during the night as the wind and current shifted. I'd awaken and think about putting on my fleece and going on deck. A simple tug on the main halyard at dawn fixed the banging and a shock-absorbing line on the anchor chain would have solved that one. It was noisy boat only because I didn't do what I knew should be done.

Sunrise brought a cool and cloudy day, not ideal for beachcombing but far better than the blizzard sailors were experiencing up North. Christine and Heather decided to savor the comfort of the boat while Walter, Suzanne, Vince and I went exploring ashore in the dinghy.

Stretching north and south for more than six miles as a wilderness barrier to the Gulf of Mexico, Cayo Costa offers unspoiled beachcombing. The cold front had kicked up the Gulf waters and the west-facing beach was piled high with shells. Sadly, the changing coastal environment from man-made and natural forces is eating away at Cayo Costa's southernmost beaches and vegetation. We wandered north along the coastline, alternately through the inland scrub growth or along the narrow beachfront as waves pounded and rolled ashore. With the vast majority of land protected as a state park, Cayo Costa's changing beauty is dramatic, powerful and sometimes distressing to witness. Mother Nature doesn't always paint a pretty picture.

Back aboard Shamrock, Heather was feeling ill and in need of some medication. We considered the options-continuing south to the South Seas Resort at Captiva Island in search of a pharmacy or heading back to Burnt Store Marina. The consensus of the crew was to head home and we expedited stowing all the loose gear in preparation for the upwind trip to Charlotte Harbor.

With both and the mainsail and the diesel doing the work in tandem, Shamrock motorsailed up the ICW past Cabbage Key and Useppa Island as we retraced our earlier route south. I checked the water but there were no visible signs of shallows. Navigating in this region by reading water is not practical in most situations as you often can't see the bottom in four feet of water regardless of the weather. It's not polluted, just the natural combination of warm water, marine growth and soft bottomland.

Safely past our turning marker, we headed east and prepared to sail the last leg home. Vince hauled on the starboard jib sheet as Christine tended to the furling line with light pressure as the headsail quickly rolled out. The sailing was superb.

During a better span of weather we could have explored Useppa and Cabbage Key, then headed out to Boca Grande Pass for coastal cruise north or south in the Gulf of Mexico. With Fort Myers, Naples, and Marco Island to the south and Venice to the north, the cruising options and opportunities both offshore and among the barrier islands of the ICW are limitless. In my opinion, it couldn't have been better no matter what Mother Nature throws your way.

More Information Cruising in Southwest Florida offers sailors the best of both worlds, coastal cruising and open sailing in the Gulf. There are lots of anchorages along the Intracoastal Waterway, protected by the chain of barrier islands that guard the mainland of Florida from Everglades north to Tarpon Springs. Two cruising guides are Claiborne Young's Cruising Guide to Western Florida and Tom Lenfestey's A Cruising Guide to Florida's West Coast. Another invaluable reference is A Guide to Anchorages in Southwest Florida, published by Boaters' Action and Information League, Inc, which provides aerial views and details on the approach route. Southwest Florida Yachts was founded by Vic and Barbara Hansen in 1984. They moved its sailing fleet to Burnt Store Marina in 1988 and the current inventory includes eight boats ranging from 24-40 feet.