Waypoint to the Spanish Main

The safe haven that voyager Juan Ponce de León claimed for his motherland in 1513 has been rediscovered countless times by sailors just passing through

St. Augustine's history, strategic location on the eastern coast of Florida, and diversity of marine facilities make it an attractive stopping-off place for cruisers with various ambitions, from the snowbirds trekking the length of the Intracoastal Waterway to voyagers sailing from the Caribbean back north via the Bahamas. And since 1941, access from seaward has been more reliably available, courtesy of an inlet dug by the U.S. Army Corps of Engineers through North Point into the Tolomato River. Even so, cruising sailors shouldn't consider this an all-weather entry point. The channel shifts frequently, and the U.S. Coast Guard has to monitor it and move its buoys accordingly.

In the late 19th century, Henry M. Flagler made St. Augustine a resort, and the city hasn't forgotten who supports this role. It welcomes cruisers and other transient boating visitors, offering a deep, protected harbor and excellent facilities. An extensive municipal anchorage occupies the city side of the Matanzas River both north and south of the photogenic Bridge of Lions that spans it. Both areas are within a short dinghy ride of the Municipal Marina, itself at the foot of the main drag.

David Moorehead, who works on the marina's docks, says the city is discussing plans to set moorings and restrict their use "to boats that are capable of moving to the marina for a pumpout every three days." He says too many junk boats limit access to transients and pose a hazard, especially those that are sinking on their moorings. Not wanting to deter bona fide cruising boats or functioning liveaboard boats, the city, he says, hopes to keep mooring fees in line with the current anchoring fee it charges those who want to use marina facilities.

"We paid $50 to anchor here for a week," Bill Warren tells me, "and that gives us access to the dinghy dock and the showers at the marina."

Bill, who's retired from the U.S. Air Force, and his wife, Nancy, a retired nurse, were visiting aboard Bel Esprit, their 1986 Hood 38, while picking their way back north in late January. They'd left their home port of Rockland, Maine, last August, and after a quick start that brought them to Annapolis, Maryland, in two weeks, they slowed down.

One of the less-well-known places they put in to along the way was Great Kills Harbor, on Staten Island, New York, which they report has a well-sheltered and roomy anchorage. After leaving Bel Esprit in Solomons, Maryland, for a month, they resumed their cruise down Chesapeake Bay and into the ICW, choosing the Dismal Swamp Canal route to Albemarle Sound.

"The Dismal Swamp Canal is so beautiful," says Nancy, "and we can't speak too highly of the people in Elizabeth City. They let us stay at the town dock for free until Hurricane Wilma went by."

One adventure they could've done without: "The transmission fell off the engine," says Bill. "Literally, it fell off, just as we were approaching the bridge at Wrightsville Beach. Our TowBoatU.S. membership paid off that day, I'm telling you." Once they'd recovered from that, they made their only foray "outside," sailing out of the Cape Fear River and going back in at Winyah Bay to re-enter the ICW at Georgetown, South Carolina.

Bill and Nancy plan to leave Bel Esprit in the Chesapeake for the summer and rejoin her in the fall to do their cruise all over again. Next time, though, they'd like a cockpit enclosure-the Hood 38's cockpit and companionway arrangement doesn't lend itself to a conventional dodger. Another modification they'll make is to fit a wind generator and solar charging panels so they can stay longer at anchor without having to run the engine.

Heading in the opposite direction were Ryan and Teresa Diehl, aboard Liberty, their South African-built Roberts Offshore 44. "We're hoping to head out tomorrow," says Ryan, "ahead of a cold front. We want to get across the Gulf Stream in the southerly winds that are forecast to precede it." Their destination was St. Thomas, in the U.S. Virgin Islands, and yes, they were a little behind the customary timetable for making such a trip. They left Baltimore on December 8, 2005, and took the inside route as far as Georgetown, South Carolina, where they jumped outside for the passage to St. Augustine.

Making up the crew were felines Eubie and Yoda, and local sailor Robbie Smith was joining them for the ocean passage. "We'll try to stay south of 30 degrees and go east until we turn right at Highway 65," Ryan says, referring to the longitude from which southbound sailors hope to reach to the Caribbean islands in easterly trade winds.

Ryan, a jazz drummer, bought the boat seven years ago from a German cruising family. "They lived very simply," he says, "so I've had to fit her out with everything." Most of that time, Liberty was in Baltimore. Teresa was an educational consultant until they quit their jobs and sold their house to embark on their cruising dream. "I've studied spa work," Teresa says. "Reflexology, Indian head massage, and so on. I'm hoping to do some of that while we're down there to help pay the bills."

Ryan's eyes rolled up in ecstasy just listening to her say the words, so no doubt they'll live well. They have no fixed plan as to how far they'll cruise or for how long. For now, they'll go as far south as they can, relaxing as they go, before heading back to the Virgin Islands and perhaps earning money doing charter work.

Tucked away on the other side of the small town, marinas and boatyards of every stripe line the San Sebastian River. Cruisers following the ICW or ducking in and out of the inlet might totally miss this aspect of St. Augustine, but it's a community vibrant enough to sustain one of the most comprehensively stocked marine consignment stores on the U.S. East Coast. Anyone immersed in fitting out their dream boat should swing by the Sailors Exchange.

Snuggled into this sheltered backwater is Oyster Creek Marina, a well-kept facility where cruising sailors can hang out at ease.

Doing just that were Kansas City, Missouri, natives Bill and Bobbi Combs. They holed up in St. Augustine last June aboard Gypsy Wind, their Bayfield 40, to wait out hurricane season.

Bill and Bobbi have been cruising for about a year. He took early retirement from a materials-handling company, and she retired from her position as CFO of a substance-abuse clinic. They trucked Gypsy Wind, which they've owned for eight years, from St. Louis to Apalachicola, Florida. After commissioning her, they sailed to Clearwater, down to the Keys, and up Florida's eastern coast to St. Augustine.

While they like to be at anchor, they're enjoying the sheltered marina. Everything they need is within walking distance, including the Sailors Exchange. Even when Hurricane Ophelia loitered off the coast for days last summer, its effect on the boats in the area was minimal. "The biggest effect it had was on the tide," says Bill. "The normal range is five or six feet, but it came up and stayed up for about a week."

Despite the reports coming from Florida about communities hostile to liveaboards, they haven't yet run into problems anchoring out. "The biggest problem we've had, and this is almost everywhere," Bill says, "was trying to find a place to land the dinghy to go shopping. All the waterfront property seems to be private, and there aren't many public landings."

Bill notes that this season's plans were delayed because of "medical issues," but he says they expected to begin heading south along the Florida coast in a few weeks' time. They're still getting used to cruising, so they have no plan set in stone, but they spoke about maybe heading farther north in the summer, to New York or Connecticut.

A few slips down from Gypsy Wind lay another boat bristling with telltale hardware of the serious cruiser--solar panels, wind generator, and antennas of every kind. "I'm a tinkerer," says Brian Bosley, her skipper. Yes, he's tinkered with Empty Pocket, a 1984 Hunter 25.5. You might also say that Manhattan master-planner Robert Moses tinkered with the infrastructure of New York City. Brian bought the boat as salvage seven years ago, and she looks as though she just popped off the production line, except for such details as the hand-drilled aluminum toerail.

If Empty Pocket is unusually well kitted out for such a small boat, it's because Brian has made hard-core cruising gear his business. He and a partner own a metal-fabrication company, Noah's Arc, across the street from the Sailors Exchange, and they're expanding into equipment for "cruising self-sufficiency." He has a patent for the solar-panel mount on Empty Pocket's stern. "The patent covers the fact that you can adjust the panels on three axes," says Brian. The solar array comes attached to a post that fastens to the boat's stern. Atop the post is a wind generator. He's ready to begin marketing the package as soon as solar panels become readily available again-most of the current supply is being vacuumed up by Europe and China.

Brian's wife, Stephanie, showed up bearing provisions. "I still can't get over what Brian's done to this boat," she says. "Have you seen below?" Brian had removed the inboard engine and fitted an air conditioner in its place (and an outboard motor on the stern). Among the gizmos tucked into every cranny was a flat-panel TV. In the forepeak was a watermaker on a portable frame. "I set it on deck and hang a weight on the intake so it stays under water," he says. "When we were in the Dry Tortugas, we could take showers in the cockpit," says Stephanie, "while other cruising boats were leaving because they'd run out of water."

To date, their longest cruise has been a month and a half, and Brian wants to see how they fare on a cruise to the Bahamas in early summer before committing to any grandiose plan. Meanwhile, they're happy that Stephanie's job-she's a physician-brought them to perpetually youthful St. Augustine, where for two years they've enjoyed the sailing and the special blend of old and new Florida that flourishes here.

Jeremy McGeary is a CW contributing editor.