Southwest Florida is one of those places where looks can be deceiving. At first glance it’s “water, water everywhere,” until you look at the soundings and then it becomes “nor any drop to, uh, sail.” But don’t give up. While it’s true the water around the archipelago west and north of Fort Myers can be pretty thin, there are still plenty of places to have a good time sailing, which is why this is regarded by many as one of the finest charters spots in the Lower 48.
Ground zero for many local sailors is Burnt Store Marina, where my wife, Shelly, our daughter, Bridget, and I picked up the Island Packet 31 Sojourner from Southwest Florida Yachts for a week of exploring this past winter.* Burnt Store is a full-service marina with plenty of deep water for sailboats, a great waterfront restaurant called Porto Bello at Latitudes, and a friendly population of manatees that loves to gather by the fresh-water conduit in front of the Platinum Point Yacht Club.
Better yet, it offers direct access to the relatively deep waters of Charlotte Harbor, which in turn provides direct access to the Intracoastal Waterway (ICW), a number of great local destinations and the Gulf of Mexico.
The first day out, we enjoyed a leisurely sail across the harbor and then tied up toward the end of the afternoon at the recently upgraded Boca Grande Marina in Port Boca Grande on the southern tip of Gasparilla Island. Boca Grande is another place where looks can be deceiving. At first glance it appears charming, but a bit antiseptic—yet another Florida community converted by developers into a safe and predictable playground for the elderly and well-heeled. Do a little exploring, though, and you soon discover there’s a lot more to this area than just manicured lawns and golf clubs.
It wasn’t that long ago, for example, that Boca Grande served as a commercial port for freighters loading phosphates mined from Florida’s interior. There’s also a thriving tarpon-fishing culture in this area, and the historic lighthouse mounted on pilings at the very southern tip of the island is a must-see if you want to learn more about the region’s maritime heritage. Those in search of a bit of “Old Florida” can also visit Whidden’s Marina on First Street. Founded in 1926, the water’s a bit shallow for anything with a keel, but the bait shop and “museum” are still well worth a visit.
Then, of course, there are the beaches. The entire western shore of Gasparilla Island (named for the apparently apocryphal pirate captain José Gaspar) is basically one great beach, replete with shells and soft white sand. Every evening small groups gather here to watch the sun go down. It’s a show that never grows old and is well worth the price of admission.
The next day we spent a couple of hours tacking back and forth across Charlotte Harbor before dropping the hook in Pelican Bay at the northern end of Cayo Costa. As with many of the harbors in this part of the world, the entrance to Pelican Bay is not for the faint of heart, and the anchorage, though expansive, is pretty shallow. Even with her 4ft shoal draft, I suspect Sojourner’s keel was resting ever so gently against the bottom later that night. Nonetheless, it’s very doable, and the sandy shoals are easy to see when the sun is out.
Cayo Costa itself is an absolute gem, a 2,426-acre barrier-island state park complete with nine miles of beach, a wealth of mangroves and even, supposedly, an alligator or two. That night, as we took a walk across the island, the sand and crushed shells absolutely glowed, looking almost phosphorescent in the light of the full moon.
The next morning we hiked around the northern end of the island and had the pine forest, Spanish moss and Live Oaks all to ourselves. Rumor has it that Southwestern Florida can get pretty hot and buggy in the spring and summer. But in the dead of winter with a fresh breeze coming in off the Gulf of Mexico, it was heaven—especially compared to the climate back home in New England.
After that we spent a night at Useppa Island, followed by a night at the South Seas Island Resort and then the ‘Tween Waters Marina on Captiva Island.
Although Useppa is a private island resort, Southwest Florida Yachts owners Barb and Vic Hansen are both members, and their charter customers are able to enjoy the added privilege of full access to this quiet, secluded gem. In addition to the larger boats in the marina, I also saw a small fleet of Marshall catboats moored just off the main beach, which I was told regularly races nearby.
Speaking of competition, the croquet “lawn” on Useppa must be seen to be believed: these are clearly people here who take their croquet very seriously. I have to say, it looked kind of fun…
Making our way south from Useppa to Captiva Island meant paying close attention to the daymarks delineating the ICW as we wended our way among various low islands and skirted the western edge of Captiva Shoal. It was the same thing, conning the narrow channels from the ICW west to the two marinas there. The approach to ‘Tween Waters was made especially challenging by the fact that a dredging crew had recently run down the red daymark marking the entrance channel—a situation I hope has since been corrected.
Equally challenging is nearby Redfish Pass, off the northern tip of Captiva Island. This is a nice deep channel out to the Gulf of Mexico, but there are shallows at either end that must be avoided at all costs. When the tide is right, the current is also fast and furious. Oh, and the channel running west from the ICW to South Seas is also the channel in from the Gulf to the ICW, so the marks are reversed, as the Gulf-ICW relationship take precedence. In other words, it’s red-left-returning because the channel also leads out to the Gulf.
Bottom line: be very careful!
It was during our stay at South Seas that we had our first good dolphin
sighting—an entire pod, in fact, chasing down breakfast just off the fishing dock around the corner from Redfish Pass. A couple of dolphins also came out to play in our bow wave later that day as we were tacking back and forth on nearby Pine Island Sound. Why is it that you can never get enough of seeing dolphins when you’re out sailing?
‘Tween Waters is aptly named: a narrow spit of land separating Pine Island Sound from the Gulf of Mexico by only a couple hundred yards. The marina is home to a substantial charter fishing fleet, countless herons and egrets, and yet another healthy troop of manatees. The pool complex is a great place to unwind, and if you’re in the mood for some kitsch, be sure to check out the crab races at the ‘Tween Waters Inn, hosted by NASCRAB Commissioner Tim. (The early show is suitable for the whole family, the later show…well, not so much.) I only wish we’d had the time to take a kayak trip across the anchorage to explore the mangroves ringing nearby Buck Key.
In addition to the usual golf courses and swimming pools, South Seas is also home to one of Steve and Doris Colgate’s Offshore Sailing schools—a fact made immediately evident by the row of Colgate 26s tied up in the middle of the marina. Complementing its basic learn-to-sail courses, the school offers a number of cruising courses for more experienced sailors aboard a small fleet of Jeanneau 439s. Sailors can also join the racing program conducted in partnership with North U.
A Drag Race Home
The next morning we cast off lines early in an effort to beat a front back to Burnt Store. The forecast was for strong southerlies veering southwest, which would be perfect for our passage: about eight miles almost due north along the ICW, then another seven or so miles east-northeast across Charlotte Harbor.
Out on the ICW, beyond the shallows just east of Captiva, we unrolled the genoa and were soon hauling the mail, hitting 5, 6 and then 7-plus knots. Sojourner was in her element! Approaching the dogleg in the channel between Useppa and Cabbage Key—which reportedly served as the inspiration for Jimmy Buffet’s “Cheeseburger in Paradise”—we rolled in some headsail to make gybing a little easier, but Sojourner kept trucking along at 7-knots-plus. The sun was shining, the dirty weather seemed to be holding back and the wind was building into the low 20s.
Making our way across Charlotte Harbor, Sojourner was even happier, but the rest of the crew—well, not so much. By now the wind was gusting into the low 30s and kicking up a sharp chop. It had also refused to shift west, so now we were sailing on a reach with the apparent wind well forward. Famed British sailor and naval architect Uffa Fox once wrote that “practically every small sailing vessel with outside ballast and a deck is able to stand far more hard driving than her crew,” and that was certainly true of Sojourner.
We hunkered down behind the dodger out of the spray and made the most of what we dubbed the “challenging” end of our brief voyage. Of course, as soon as we were in the lee of the twin islands guarding the entrance to the channel at Burnt Store, life was good again.
Making our way toward the fuel dock to pump out and take on diesel, I even had to drop the auxiliary into neutral when Bridget spotted the ripples from a manatee lounging just off our bow—a great way to end a great week sailing Southwest Florida.
(Ed note: Southwest Florida Yachts recently consolidated its operations in Cape Coral, FL, a short distance from Sanibel Island. See “Sail Away” on page 64 for details.)
Do you want to read about more Charter destinations? Try another story.
Adam Cort is SAIL’s Executive Editor.
He sails with his wife and daughter,
a budding professional wildlife-spotter