Fort Myers sprawls along the banks of the Caloosahatchee (meaning “river of the Calusa” Indians), twelve miles upriver from the Gulf of Mexico. The River is part of the Okeechobee Waterway, which begins at Stuart, on Florida’s east coast. The estates of both Thomas Edison and Henry Ford in downtown Fort Myers are just two of the shore-side attractions for the cruising tourist. Beautiful riverfront homes and a variety of marina facilities, including the City Yacht Basin, make a cruise up the River quite relaxing, with both interesting and convenient stops along the way. If you are lucky, you might even have a pair of “wake-dancing” dolphins escort you on this delightful sojourn.
Heading north from Fort Myers, the Intracoastal Waterway winds its way through the barrier islands of Sanibel, Captiva, Cayo Costa, and Gasparilla. These are the islands that make Southwest Florida famous. Our passage takes us first through Pine Island Sound. Fifteen miles long and four miles wide, the Sound is protected by the barrier islands to the West and Pine Island to the East, and affords the cruiser countless islands and keys which offer unlimited anchorages and abundant bird and marine life to observe. If there is a landlubber in your crew, many fine marine facilities and award-winning restaurants dot the islands.
Two resorts, ‘Tween Waters’ and ‘South Seas Plantation,’ offer such things as fine dining, entertainment, specialty shops, canoeing and jet ski rentals. And you will want to be sure to catch the famous Florida west coast sunset from any of the island beaches.
If you prefer anchoring, try the bight on the inland side of the Wildlife Refuge on Sanibel Island. When there’s a northerly or northeasterly breeze, you may want to drop the hook in the lee of York or Chino islands on the mainland side of the ICW channel. If you plan to head out into the Gulf from here, Redfish Pass between Captiva and North Captiva is navigable; however, it is best to ask for local knowledge for Mother Nature’s latest changes to the cut.
One of the most beautiful of the barrier islands is Cayo Costa. A tropical paradise, the island is now a State Park and offers excellent shelling, beachcombing, swimming and dramatic sunsets. The southern tip of the island offers a lovely day anchorage on your cruising itinerary.
No cruise through Southwest Florida is complete without a stop at Cabbage Key. This picturesque island has been made famous by such well-known cruisers as Jimmy Buffet. Rumor has is that Cabbage Key was the inspiration for Jimmy’s song, “Cheeseburger in Paradise!” And there’s nothing quite like a cool libation at the island bar which is decorated in a unique wallpaper – dollar bills! The former home of mystery writer Mary Roberts Rinehart, this island estate has been transformed into a world-famous “watering hole” for cruisers from near and far. A stop at Cabbage Key is a “must” in any skipper’s float plan!
The jewel of Southwest Florida’s cruising crown might just be the private tropical paradise of Useppa Island. Useppa is a private island club. As members, Vic and Barb Hansen can offer their charter guests access to Useppa.
Cruisers who visit Useppa may enjoy a drink in the Tarpon Bar, dinner in the historic Collier Inn, or a dip in the pool or hot tub. All of the first-class amenities are set in a beautiful, lush tropical atmosphere.
When the wind picks up, Charlotte Harbor at the northern tip of Pine Island Sound offers beautiful and protected cruising. for this reason, and its close proximity to the enchanting barrier islands, the Harbor is home to our own ASA ( American Sailing Association) Sailing School at Burnt Store Marina, one of the nicest marine resort facilities in the area.
Directly across the Harbor to the west is Boca Grande ( “big mouth” ) Pass, a commercial shipping channel as well as home to the world-famous Tarpon and hundreds of fisherman who pursue them. The Pass is well-marked, providing easy access between the Gulf and Charlotte Harbor in all kinds of weather conditions.
To the north sits the town of Boca Grande on Gasparilla Island. The island was named for one of the most famous early settlers, the Spanish pirate Jose’ Gaspar. Gaspar and his roving “banditos” strategically stationed themselves just off the channel where they could easily pillage passing ships of their precious cargoes.
Beyond Gasparilla to the north, the ICW winds through scenic Lemon Bay in route to Venice. Taking the outside track from Boca Grande Pass, you have access to the ICW again at Venice Inlet. Venice offers convenient dockage facilities and a great restaurant at the Crow’s Nest.
Now that you’ve had a “taste of the islands” of Southwest Florida, let’s head south from Fort Myers and sample another area of beautiful cruising, including Naples, and Marco Island Heading south, the ICW ends for a time and the Sanibel Bridge forms the “gateway to the Gulf” and the coastal communities of Naples and Marco Island. Once through the Bridge, you’ll commence the twenty six mile passage to Naples, the first stop on our cruise toward the state’s southern tip. The prominent fishing pier makes for an easy landfall to Gordon Pass and the entrance to the world-renown Naples. Anchor amid the mansions lining the canals leading to town, or tie up at the City Docks. Either way, you can experience the sights and sounds of this Mecca for the “rich and famous”. Not all the dining is “five star”, however. There are dockside dining spots like “The Dock,” and pubs for a variety of cruising pocketbooks.
Just seven miles south of Gordon Pass is Marco Island. The inside route from Naples southward on the ICW is a treat for nature lovers young and old. Alligators, raccoons, bald eagles, osprey, and manatees are just a few of the “friendly natives” you may encounter along the way. Now a model of resort living, Marco Island offers a number of marina and leisure facilities.
Having explored the coastline from Gasparilla to Goodland, we have only experienced two-thirds of what Southwest Florida cruising has to offer. From Fort Myers, heading East, the Okeechobee Waterway will take you on a cruise akin to the “African Queen” as you journey to Stuart on Florida’s east coast.
The Waterway affords a unique cruising experience to motor yachts, trawlers, and small sailboats. While controlling depth of the Waterway is eight feet, the mast height restriction of 49 feet at Port Mayaca on Lake Okeechobee’s eastern shore prohibits large sailboats from making the entire trip from west to east. However, between Fort Myers and Port Mayaca is some of the most beautiful scenery along the Waterway.
You will transit five locks in your cross-state cruise. All locks are manned by capable and courteous lock tenders; however, hours of operation are limited. You will need to consult your Waterway Guide for specific information.
Following the route of this once-bustling water “highway” is like stepping back in time. The scenery is wild and tropical, complete with alligators basking in the sun and bald eagles soaring overhead. You will pass by pioneer Florida settlements such as Labelle and Moore Haven, through acres of pastureland with grazing cattle, and along rows of citrus groves lining the shore. All in all, the trip is a soothing sojourn through a part of Florida rarely seen by most visitors to the state.
At Clewiston, you must choose between the scenic “rim route” around Lake Okeechobee, or the direct route across. Surrounded by sugar cane fields, Clewiston is known as the “sweetest town in the U.S!” You won’t want to miss dining at the Clewiston Inn which is well-known for its style of southern cuisine that has served many generations. Clewiston also sits in the heart of the best Lake Okeechobee bass fishing. A number of “fish camps” dot the Lake and guides are available to the novice fisherman.
The direct route across the Lake will shave ten miles off the cross-state trip, and is recommended for vessels over five foot draft. However, the Lake is wide and shallow and gets very choppy in rough weather.
Once reaching the fifth and final lock, the St. Lucie lock, our destination is in sight. The St. Lucie Canal will lead you to Stuart and the “sailfish capital of Florida.” Fine marinas and resorts are plentiful, catering to the large fleet of sportfishing and luxury yachts which are common sights on the “Gold Coast.” The hustle-bustle of the East coast is in stark contrast to the world we left behind.
While the joy of cruising is found with each new day and in each new anchorage, the greatest joy for us is in returning home at the completion of our cruise – “home” to beautiful Southwest Florida!