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A cold and windy Keys escape

Taking along a kayak aboard Amtrak's Auto Train in January for two weeks of paddling in the Florida Keys called for a rugged, small inflatable that would fold up and stow inside my car.

I thought it might also perform additional duty this summer on Chesapeake Bay as my tender and as a fairly stable boatwork platform, able to fit inside my boat fully inflated when cruising. I named it Gonzo because handling such offbeat functions may also aid in my kind of participatory boating journalism.

Jack Sherwood

West Marine's Skedaddle 1-XC Solo Kayak, at $250, is not a toy and could replace my 8-foot Walker Bay hard dinghy, which strays under tow and is tippy. This new 8-foot, 4-inch paddler, however, with a beam of 34 inches and weighing only 19 pounds, is easy for an older gent like me to car-top and launch fully inflated. Hopefully, it will fit in my V-berth inflated, with the bow protruding a few feet into the curtained anchor well. We shall see.

Resting bottom-up on the car's roof and held fast by four lines, it did not go airborne in Florida, even traveling at 70 mph with sudden gusts from passing 18-wheelers. But I was in for a big, upsetting surprise on my arrival in Islamorada, when wind and record-low temperatures in the mid-40s continued for the duration of my visit, limiting kayaking and beachcombing in general.

I figured there would always be colorful boaters to interview, especially in the Keys. A boating writer like me is able to introduce himself to strangers following the watery trails in life and start asking a lot of questions about how they got to where they are. Dropping the name of Soundings magazine also helps a nosey, pale, old dude from up north - with white hair and whiskers - spin his yarns.

I had originally planned my first launch at Marathon Key's Sombrero Beach and thence through some mangroves into Boot Key Harbor. This was the home port of a colony of colorful boaters I met five years ago when the city began a campaign to discourage "permanent," itinerant liveaboards anchored out or secured to mangroves in picturesque but unseaworthy craft.

While crawling around in a winding maze of greenery, I came across none of those "mangrove monkeys" - all appeared to be gone, replaced by nature's assorted crabs, egrets on spindly legs, and green iguanas sunning themselves. But the freakish cold snap knocked iguanas off branches and killed fish struggling to find warmth on the surface of exceptionally cool water. Kayak rental stations, mobile and stationary, were also relatively inactive. Even salty hangers-on at the harbor's outdoor Dockside Bar huddled in winter garb behind weather curtains, seeking warmth around electric space heaters.

Looking for an ocean-washed shoreline that might draw some hard-core paddlers eager for conversation, I left Marathon behind and headed over the Seven Mile Bridge to Bahia Honda State Park. There was no activity on the cold, windswept Atlantic side unprotected by offshore reefs, so I drove to the Gulf side looking for a lee and found a small-boat single-hander about to resume his passage north along the shipwrecked Straits of Florida.

Ferd Johns, 68, of Bozeman, Mont., sat in his 1988 Sanibel 18 sloop at the park's small marina basin with a 3-1/2-foot entrance depth. A professor emeritus of architecture at Montana State University, he had left home Dec. 28 in minus 9 F temperatures aboard a small van with his trailer-sailer, Widget, under tow. He launched on New Year's Day in the Florida Panhandle and, like me, was cursed for two weeks with cold and windy weather.

Like the Bay Tripper, Montana sailor Ferd Johns had escaped to the Keys but was greeted by record-low temperatures in the Sunshine State.

Shifting his van to and fro to pick up and drop off one sailing guest at a time, Johns had the right boat for Keys cruising. Widget draws just 12 inches with her rudder and retractable centerboard raised, and she's rigged for single-handing, with tight quarters down below. Plans call for trailering her to the Chesapeake, where he will leave the boat and resume cruising in the spring.

Unfortunately, I encountered the "rustic" Key Lime Sailing Club in Key Largo on my last day in the Keys. This small, funky, laid-back beach community of "cottages" on huge Buttonwood Sound is straight out of Old Keys Central Casting. A retirement home for older, indifferently maintained keel and centerboard sailboats, the "resort" offers a "free" sailboat with each individual cottage rental and escorted cruises into the Everglades.

Scattered about the premises are some 70 watercraft of all descriptions - Sunfish, Lasers, inflatables, kayaks, dinghies, runabouts, canoes, surfboards and other assorted platforms that float. Paul Keever, the owner, cannot turn down a good deal when it comes to small, orphaned boats with blown-out sails. He has a tough time keeping count of his active, inactive and terminally ill fleet hanging on moorings, tied up at two rickety piers and in the sand among palm trees.

It is a hard place to find, so look for a non-descript "Boats for Sale" lot just below Mrs. Mac's Kitchen, a local favorite since 1976 at Mile Marker 99.4. If you're in a non-demanding mood, willing to tolerate low-maintenance Keys lodging and not particular about service or amenities, a phone call to (305) 451-3438 will be your ticket to a free sunset sail aboard the queen of the fleet - a modified 40-foot catamaran with a sliding board.

During the final two days of my visit south, I stayed with my oldest son and his family at their home in Fort Lauderdale. He and I drove to Naples on the Gulf Coast, where I found the exact opposite of Key Lime Sailing at the Naples City Dock. Veteran owner/cruiser Marlena Brackebusch offers captained and bareboat charters aboard an immaculately maintained 2007 Catalina 309 with roller-furling sails and plenty of electronics. She also puts together other packages with different captains and vessels.

Aboard Island Dreams, we motored for a half-hour past elegant homes along the narrow Naples Bay Channel to reach Gordon's Pass and the Gulf of Mexico, where the captain rolled out the sails. I took the wheel and off we went, reaching on a two-hour sail under warm and brilliant skies with the perfect 10-knot breeze I had not found in my two weeks in the Keys.

Jack Sherwood is writer at large for Soundings.

This article originally appeared in the April 2010 issue.