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  • Writer's pictureCaptain Mark and Suzanne

St. Augustine, Florida - A Chesapeake Cruiser's Winter Haven.

Ahoy Crew! Happy 2020 to you!

St. Augustine, A word of truth

Home of the fabled Fountain of Youth

Not too hot! Not too cold!

The Ancient City never gets old!

After an ambitious 2019, beginning with a cruise from St. Thomas to Rock Hall via Puerto Rico, Turks and Caicos, The Bahamas and Florida, followed by a busy charter season in Rock Hall, Suzanne and I decided it was time to take a break, relax and enjoy the cruising life a little closer to home. At less than 1000 nautical miles south of Rock Hall, we pointed Island Girl toward  “America’s Ancient City”, St. Augustine, Fl. Having made a short stop on our way up the Florida coast last year, it was clear that St. Augustine is a special haven that we wanted to revisit in cruising style. 

St. Augustine represents the very best of many possible worlds. As a colorful cruising destination, the city and its surrounding areas cannot be beat. With a large live aboard community, the town boasts a myriad of marinas, yacht services, marine supplies and provisioning opportunities. The City operates a world class marina that that sports an exceptional staff, very reasonable floating docks and three large mooring fields for long term and transient vessels. For those on a tighter cruising budget, the free anchorage is roomy with easy access to town from the municipal marina dinghy dock. Because the city is located right on the ICW as well as a major ocean inlet, the cruiser can dinghy to nearby places such as Vilano and St. Augustine beaches for a completely different Florida vibe.

As a cultural center, St. Augustine stands out as a premier touring destination for anyone that loves 16th and 17th century Spanish history and architecture. Amid the conclave of well-preserved and restored buildings, streets and alleyways, there is more to see and do than one can imagine.  The famed Castillo de San Marcos, the nation’s oldest masonry fort, stands watch at the harbor’s edge as the awe-inspiring Flagler College, the exotic Liechtner Museum and numerous fine art galleries grace the busy King St just a few steps away from the marina. St. George St. and the entire waterfront bustles into the wee hours with bars, restaurants, live music, shops and happy hours galore. When it comes to festivals, events, and stories of pirates and ghosts, it is no wonder why the streets of Ancient City are flush with horse drawn carriages, trams, trolleys and enthusiastic tourists seven days a week. 

Suzanne an I had hoped to reach St. Augustine before Thanksgiving after leaving Rock Hall on November 1st. With a few nice weather windows, a mix of offshore and ICW sailing, and several anticipated stops, we were able to complete the journey by November 23rd. Perfect timing! Upon our first sunset, we found ourselves relaxing aboard Island Girl tucked into a beautifully secure and centrally located slip with a front row view of the annual “Nights of Lights” celebration. This two month long city-wide holiday event features the brilliant illumination of every building and palm tree in town, and extends all the way across the Bridge of Lions to Anastasia Island. The visual impact is simply jaw-dropping and is impossible to describe! 

Perhaps, our most memorable experience this winter will be the St. Augustine Cruiser’s Net (SACN), and the huge number of wonderful people we have met. I should have figured as soon as I saw the Spinsheet Magazines in the cruisers lounge that we would encounter many Chesapeake sailors. SACN is an active and most welcoming volunteer organization for cruisers who are arriving, departing, and for those who have decided to stay. Realizing that without a reservation, there would be no hope of finding Thanksgiving dinner at a restaurant, we were thrilled to be invited to  SACN’s annual Thanksgiving potluck dinner. It was an outstanding meal with over 140 people in attendance. What a wonderful opportunity to meet people from near and far. The initial conversations usually start with, “Where are you from and where are you going?” Our responses have become pretty standard – “Rock Hall, Md” and “We’re already here”! At one point, at a SACN happy hour, we sat between two couples who, like us, had never met each other. When I replied, “Rock Hall” to the couple on our left, the couple on our right perked up and stated that they attend Pirates and Wenches Weekend every year and anchor their boat in Swan Creek. At that point, the couple on our left, chimed in that they too anchored in Swan Creek for last year’s pirate event. It turns out that both boats were anchored together in Rock Hall at the same time! I guess it goes to show that the cruising world is quite a small world within a very large world. And, whether we are cruising to St. Thomas, St. John, or St. Augustine, we are never too far from St. Michaels, St. Mary’s or any of the other many Chesapeake destinations that we can proudly call our home.

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