Cruising Stories

Cruising Sanibel and Captiva Islands in the Gulf of Mexico

Southwest Florida Winter Destinations

Capt. Jeff

Both Sanibel and Captiva Islands are marketed with the motto Naturally, you'll love it here. That tag line sets the tone for both of these Southwest Florida winter destinations on the Gulf of Mexico. They are sanctuary islands that are committed to the preservation of their flora and fauna, limited growth and development, and both look at tourism with a wary eye.


Sanibel was named after Queen Isabella of Spain, and is believed to be a contraction of Santa Isybella or Santa Ybel for short. While the 16th century Spaniards never inhabited the island, the first modern settlement on Sanibel was established in 1832 by the Florida Peninsular Land Company. Although this colony didn't last, it was the first to petition for a lighthouse at the eastern tip of the island. Sanibel Light was finally built in 1884 to guide the schooners past the shoals of San Carlos Bay.

In the 1970s, Sanibel became a popular retirement location for ex-CIA members, led by Porter Goss who was working in clandestine services. Goss eventually edited the island's newspaper, became the island's mayor and represented Southwest Florida in Congress for many years.

The J. N. Ding Darling National Wildlife Refuge is located on Sanibel. The 6,354-acre refuge located on the back bay side of the island was established in 1976, to protect one of the country's largest undeveloped mangrove ecosystems. More than 220 species of birds, 50 types of reptiles and 32 kinds of mammals call this place home. There are numerous walking, bike and canoe trails for all types of explorers.

If you enjoy shelling, then the beaches of Sanibel Island offer the best location to pursue that hobby in Southwest Florida. If The Beaches of Fort Myers & Sanibel, Lee Rose you are new to shelling, you will soon learn the Sanibel stoop as you walk along the beach bending down in hope of finding that rare junonia shell. And if you just want to learn more about shells, visit the Bailey-Matthews National Shell Museum on Sanibel.Sanibel is also home to BIG ARTS (Barrier Island Group for the Arts) which presents world-renowned music and dance, intimate live theater, distinguished speakers, arresting art exhibits, fine films and workshops taught by gifted artists and instructors for Sanibel and Captiva's residents and visitors.


Captiva, according to local folklore got its name because the pirate Jose Gaspar kept his female prisoners captive there for ransom. Gaspar was the scourge of the west coast of Spanish Florida and legend has it that Gaspar met his end in December 1821, the year that Spain sold its Florida territory to the United States. The pirate had decided to retire after almost 40 years of plunder, and he and his crew were dividing their vast treasure at their base on Gasparilla Island, a few islands north of Captiva. A pirate lookout spotted a heavily-laden British merchant ship that was too good to pass up for one last haul of booty. As they approached the merchantman, it hoisted the American flag. It was not a British vessel at all, but the U.S. Navy's schooner Enterprise. Gaspar's ship was riddled by cannonballs and, rather than surrender, he supposedly wrapped an anchor chain around his waist and dramatically leapt from the bow shouting, I die by my own hand, not the enemy's!

Clarence Chadwick, an entrepreneur, purchased a 320-acre parcel at the northern tip of Captiva in 1925. Working with a local farmer, he developed a salt water-resistant key lime, which he planted along with coconut palm trees on his farm. Chadwick built a warehouse and dock for shipping his fruit, and his plantation became the largest producer of key limes in the world. By 1942, Chadwick was very ill and decided to sell his business. The warehouses and farm workers' cottages were turned into a small fishing camp that became the nucleus of what is now South Seas Island Resort. The resort is the perfect place to experience Captiva's unique ecosystem with the Sanibel Sea School a marine conservation education program for both families and kids.

As cruising destinations, Sanibel and Captiva offer some the best of beaches, fishing, boating, shopping and dining that Southwest Florida has to offer. Dock space for transients is limited at the marinas, so make your reservations well in advance. Boats and bicycles are the best ways to enjoy their island lifestyles. If you are a sailor, the steady northwesterly breeze after a winter cold front passes through provides challenging sailing on the Gulf of Mexico. If you prefer to fish, on calm days, Redfish Pass and Blind Pass provide superb fishing. Either way, do plan on spending a couple of weeks this winter enjoying both islands.


  • Sanibel Marina is just about a mile away from the Sanibel Lighthouse and across San Carlos Bay from Fort Myers Beach. The marina is also home to Gramma Dot's Seaside Saloon, a locals' choice for lunch or dinner.
  • Yacht Harbour and Marina Located at South Seas Island Resort, the marina offers fuel, shower and laundry facilities for vessels up to 120 feet in length. The marina can be reached via the Gulf Intracoastal Waterway heading 10 nm north of the Sanibel Causeway or entering Redfish Pass from the Gulf of Mexico between Captiva and North Captiva.


  • Thistle Lodge at Casa Ybel Resort Enjoy beachfront dining and a wonderful Sunday brunch. The Lodge is an historic 19th century home. (239-472-9200,
  • Bubble Room Words cannot describe the eclectic nature of this restaurant. From the uniforms of the servers to the restaurant's decor chock full of memorabilia, it is always a night to remember. And do save room for dessert! (239-472-5558,

Capt. Jeff Werner has been in the yachting industry for over 25 years. In addition to working as a captain on private and charter yachts, both sail and power, he is a certified instructor for the USCG, US Sailing, RYA and the MCA. He is also the Diesel Doctor, helping to keep your yacht's fuel in optimal condition for peak performance. For more information, call 239-246-6810, or visit All Marinalife members receive a 10% discount on purchases of equipment, products and supplies from Diesel Doctor.

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