Written by Capt. Jeff Werner
January 2018

Boating north from Southwest Florida allows two routes to reach your destination. The Florida Gulf Coast offers both enjoyable and sometimes challenging cruising. In the winter, on days when the winds are light, power boats rule. However, when a cold front passes through, the blustery northwest winds leave the waters free for experienced sailors. Fortunately for boaters, the Gulf Intracoastal Waterway (GIWW) allows for safe cruising on back bays behind the barrier islands when the weather turns. For this extended weekend cruise, the distance to each destination in nautical miles is noted for both a Gulf of Mexico run and the GIWW.

Estero Island, also known as Fort Myers Beach, is a barrier island on the Gulf of Mexico that lies just south of the junction that marks the western end of the Okeechobee Waterway and the beginning of the Gulf Intracoastal Waterway. Fort Myers Beach has a rich history dating back 2,000 years to the Calusa Indians.

The best spot to dock on Fort Myers Beach is the Pink Shell Resort & Marina (877-685-9826). Experience its spa and resort features while secured to the floating docks adjacent to Bowditch Point on the north end of the island.

Begin your tour of the island with a bit of time travel at the Mound House. Walk inside a Calusa Indian shell mound and discover the indigenous culture that Ponce de Leon met as he searched for the Fountain of Youth. Tour the William Case House that was built atop of the shell mound and has been restored to its 1921 grandeur.

A peaceful trail walk through an unspoiled mangrove canopy and oak hammock along the Back Bay awaits you at the Matanzas Pass Preserve. Observe the ora and fauna native to Southwest Florida at this unique park that includes the Estero Island Historic Cottages at the park entrance.

Since the 1950s, Fort Myers Beach has been home to a large fleet of Fort Myers Beach Fishing Pier shrimp trawlers that harvest “pink gold” from the Gulf of Mexico. Dinghy over to San Carlos Island to visit the shrimp boats. Take a self-guided walking tour of working shrimp fleet, and don’t forget to buy some fresh pink shrimp right at the shrimp docks.

For dinner, SOB is a must! The Smokin Oyster Brewery serves Garlic Crab, a special combination of Dungeness crab, secret spices and butter. Your only regret will be wishing you were not casting off the next morning, so you could come back for more.

DAY ONE

Punta Gorda – Gulf of  Mexico 50 NM, GIWW 39 NM

Burnt Store Marina (941-637-0083) is located on Charlotte Harbor, an estuary that is the second-largest bay in Florida. Charlotte Harbor is a thriving commercial, recreational and sport fishery and has excellent waters to sail upon. Burnt Store is also easily accessible from both the Intracoastal Waterway and the Gulf. Although it is a secluded and quiet destination, the marina is a reasonable taxi ride away to downtown

Punta Gorda, and plenty of shopping, restaurants and things to do. Punta Gorda is located at the mouth of the Peace River, and in 1896, it was the largest phosphate shipping point in the world. Phosphate, used for agriculture and industry, was found along the banks of the river upstream of Punta Gorda. Today, the city caters to tourism, as does the majority of Southwest Florida.

The Muscle Car City Museum is a mecca for aficionados of GM performance cars, such as Corvettes, Chevelles and GTOs and other models dating back to the 1930s. Fishermen’s Village has the most popular collection of boutique shops and restaurants in town. It also hosts an array of special events and live music throughout the year. Harpoon Harry’s, at Fishermen’s Village, has been named “Best Waterfront Restaurant,” “Best Open-Air Restaurant,” “Best Place to Have a Beer” and “Best Bar & Night Spot” for many years.

DAY TWO

Longboat Key – Gulf of Mexico 78 NM, GIWW 58 NM

Longboat Key is best known for its 12 miles of relaxing white sand beaches. On the south end of the island is Mote Marine Laboratory & Aquarium, an institution comprised of world-class marine scientists committed to the belief that the conservation and sustainable use of our oceans begins with research and education. To that end, a family visit to Mote’s Aquarium gives an up-close experience with a variety of marine animals and fish, including two touch tanks and a 135,000-gallon shark habitat. It is a working aquarium, meaning that scientists are conducting research in viewable working laboratories, offering a unique experience to visitors.

A short drive south of Mote Marine Laboratory and Aquarium over the New Pass Bridge is St. Armands Circle, Sarasota’s well-known destination for shopping, dining and pampering. Luxury fashion, jewelry and gift shops abound. For a very special dinner on the Circle, make a reservation at the iconic Café L’Europe a restaurant that has built an unparalleled reputation for its elegant and delicious European cuisine.

The Longboat Key Club Moorings (941-383-8383) is a yachting resort located off the GIWW complete with a swimming pool and tennis courts. It is a prime location for docking, and boaters have access to all the amenities of the Resort at Longboat Key Club including the golf courses and spa.

DAY THREE

Bradenton – Gulf of Mexico 33 NM, GIWW 23 NM

The city of Bradenton is located where the Manatee River feeds into the entrance to Tampa Bay, just south of the Sunshine Skyway Bridge. It is also the home of the De Soto National Memorial. In May 1539, Spanish conquistador Hernando De Soto’s army of soldiers, craftsmen and clergy made landfall in Tampa Bay. They were under orders of King Charles V to conquer, populate, and pacify the land in Florida. Instead this expedition was met with fierce resistance from the indigenous people. Spanish plans for colonization were set back, and it was another 300 years before American pioneers decided it was safe to settle in Bradenton.

Tie up at Twin Dolphin Marina (941-747-8300) just west of the bridges in downtown Bradenton. is 225-slip marina, with floating docks, surrounds the historic Memorial Pier. The Pier’s building was built in 1928 and has now been meticulously restored completely preserving the building’s Spanish style.

The South Florida Museum & Bishop Planetarium is the largest natural and cultural history museum on Florida’s Gulf Coast, and it offers engaging exhibits as well as educational programs that interpret the scientific and cultural knowledge of Florida. The planetarium is the region’s premier astronomy education facility with a multimedia theater for films, lectures, live music and digital art performances.

A short walk from the marina is Arts & Eats Restaurant and Gallery. Its diverse menu highlights flavors from all over the world. The restaurant is located in Village of the Arts, a business and residential community where artists live and maintain studios in restored cottages from the 1920s and 1930s. is village is one of the many hidden gems to be discovered while cruising the Gulf Coast of Florida.