Our journey started as we pulled out of Waterford Harbor Marina in Kemah, Texas, in May aboard our sailing vessel Fidelity, a 42-foot Valiant. My husband, Kevin, Windy, our Boston terrier, and I were excited to cross the Gulf of Mexico and explore the many towns that dot the shores of Florida with hopes of finding our future homeport. Oh, the places you’ll go with a 6-foot draft and 60-foot mast!
After crossing the Gulf of Mexico, our landfall was Clearwater Harbor Marina, which provides easy entry from the Gulf and plenty of deep water for a 6-foot draft (as long as you stay in the channel). The marina’s floating docks are key, especially when the swift current catches. The facility is conveniently located near Cleveland Street, Clearwater’s entertainment district. It’s an easy trek to the beach by water taxi or a stroll over the bridge. Frenchy’s Original Cafe´ is a must-do for the famous Florida grouper sandwich.
After a lovely day cruising about 40 miles offshore, we made our way to the Harborage Marina at Bayboro in St. Petersburg. We arrived after closing and were greeted by Leon, the night guard, who provided us with the ever important “keys to the gate.” Windy thoroughly enjoyed her time at the marina, given the surplus of dog treats provided by the staff, which made it one of the most pet-friendly marinas we visited. It’s number one on our list of possible homeports after our adventures on Fidelity wind down.
Just a short walk from Harborage is historic downtown St. Petersburg. Among other don’t-miss spots, The Chattaway has great burgers and cold beers. No car is needed — unless you want to make the trip to Mazzaro’s, the best Italian market ever. Nearby, Island Nautical does great service work and repairs. We installed new dingy davits from MarTek and bought a new dinghy to hang off them.
After our stay in St. Pete, it was time to get Fidelity a little farther south. We made a quick stop at Longboat Key then continued on to the Venice Inlet to Crow’s Nest Marina and finally arriving at Boca Grande Marina on Gasparilla Island. The approach into Charlotte Harbor was easy, the narrow channel and turn into the marina well marked, and the marina staff talked us into the harbor to avoid the shallows. The marina’s docks were pristine, and the on-site restaurant, Miller’s Dockside Bar & Grill, was the perfect place to settle into upon arrival.
Golf carts are the preferred mode of transportation in these parts — Windy loved riding around and eating at the Loose Caboose, where she ordered from the doggie menu. The landscape’s many banyan trees are remarkable, and the pastel-colored “old Florida”-style homes are atmospheric and beautiful. It was a great spot to slow down and enjoy the quieter side of things.
Before we got too settled in this lovely place, we decided to move on. We awoke to a thick layer of fog that lifted by mid-morning, when we were already well underway to our next stop, Pink Shell Beach Resort & Marina in Fort Myers Beach. On approach, the busy port was full of commercial and recreational boats but provided a good depth for Fidelity and was extremely easy to navigate.
Dave, the marina’s harbormaster, was incredibly hospitable, but unfortunately we were forced to leave early due to an approaching storm front. We set sail for Marco Island Marina, which would be our home for the next couple of months. As we approached Capri Pass, we were thrilled by the sight of boats sailing in the waters of Marco Island.
Marco Island is a great port with easy access to Gulf sailing, deep water and plenty of dining and entertainment options. The channel into the marina is well marked and the fairways are wide enough for an easy docking experience. Some of our favorite spots for a bite to eat during our time there were the Island Gypsy Cafe´ (a dinghy ride away from the marina), the Italian Deli (excellent New York-style pizza) and the Esplanade.
After several months on Marco Island, Fidelity was ready to head to Key West. By now, Chris Parker, the weather guy, had become Fidelity’s most important satellite crew member. There was a small window between storm fronts so we took it and sailed to Stock Island Marina Village in Key West. We had a fun stay, and the marina shuttle was more than sufficient for exploring downtown Key West.
Marathon Marina and RV Resort was our next stop. The marina has new, concrete floating docks, and the on-site Lazy Days South was the perfect spot for happy hour and dinner.
Then it was on to Miami. We cruised past Key Biscayne and downtown Miami to Miami Beach Marina. Giovanni, the dockhand, was a pro with the lines, which came in handy because a strong current surges through the marina — but the prime location makes the effort worth it. We enjoyed South Beach’s Art Deco architecture, not to mention the bars, restaurants and beach, and then decided it was time for our next destination, Fort Lauderdale.
Bucking the current through Government Cut, Fidelity had her first sail in the Atlantic. Our timing was near perfect with the 17th Street Bridge opening, and a quick turn put us into the Hyatt Regency Pier Sixty-Six Marina. The on-site restaurants, Grille 66 and Pelican Landing, were both great dinner spots. A little bit farther aheld, Louie Bossi’s Ristorante Bar Pizzeria, 15th Street Fisheries, and South Port Raw Bar rounded out our top picks for food, atmosphere and price in Fort Lauderdale.
Soon enough, it was time to get underway to Jacksonville and up the coast before hurricane season. A few quick stops we made during this leg of the trip deserve mention. Lake Park Harbor Marina, just north of Riviera Beach, is a great stopover, with floating docks and a low-key atmosphere. Fort Pierce City Marina in Fort Pierce is another wonderful destination — the floating docks were in excellent condition and the staff knowledgeable. At Cocoa Village Marina in Cocoa Beach, the dockmaster and crew greeted us personally and made us feel right at home. And Hammock Beach Resort in Palm Coast was a true luxury — with swimming pools, restaurants, and doggie treats for Windy.
After the 20-plus-nautical-mile, winding ride past Matanzas Pass, we pulled into the St. Augustine Municipal Marina, and the masterful docking crew handled everything like a finely tuned machine. St. Augustine was a particularly lovely stop and is number two on our list of top ports of call, offering everything from history to dining to shopping. Windy loved her morning walk through the historic part of town, and almost every restaurant we visited welcomed her with a bowl of ice water.
But hurricane season was approaching. It was time to move Fidelity to her summer home. We sailed offshore and then motored up the St. Johns River to Jacksonville’s Marina at Ortega Landing. And then we immediately began to look at locations where we might put her in the winter, and to make plans to explore the East Coast in the spring. With so many great ports to chose from, we have some homework to do.
