The waters off Southwest Florida are one of those places where looks can be deceiving. At first glance, it’s “water, water everywhere,” until you look at the depths and then it becomes “nor any drop to, uh, sail.” But don’t give up. While it’s true the archipelago to the west and north of Fort Myers can get pretty shallow, there are still plenty of places to go sailing, making this one of the finest charter 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 all the services you could hope for; 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 freshwater conduit in front of the Platinum Point Yacht Club.
Better yet, the marina offers direct access the relatively deep waters of Charlotte Harbor, which in turn serves as a kind of local hub, linking up with the Intracoastal Waterway, a number of great nearby 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 that has been 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 substantial commercial port for freighters loading phosphates mined from Florida’s interior. There’s also a thriving tarpon-fishing culture here, 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 there 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 pirate captain José Gaspar) is basically one great beach, replete with shells and soft white sand. Every evening small groups gather there 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 is the case 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 four-foot shoal draft, I suspect Sojourner’s keel may have been resting ever so gently against the bottom later that night. Nonetheless, it’s very doable, and the sandy shallows are easy enough to see when the sun is out.
Cayo Costa itself is a 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 lurking about in its weedy corners. That night we took a walk across the island, and the wide, white-sand and crushed-shell pathway absolutely glowed, so that it appeared almost phosphorescent under the light of the full moon.
The next morning when we went for a hike around the northern end of the island, we had the pine forest, Spanish moss and Live Oaks all to ourselves. Apparently 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—certainly compared to the meteorological doings back in New England.
Useppa is a private island. However, Southwest Florida Yachts owners Barb and Vic Hansen are both members, so their charter customers are able to enjoy full access to this quiet, secluded haven. I was happy to hear that the small fleet of Marshall catboats moored just off the main beach takes part in a regular series of races on the shoal waters to the west of the island. The croquet “lawn” there has got to be seen to be believed: these are clearly a people 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 day marks on either side of 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 day mark denoting the entrance channel—a situation I’m sure has since been corrected.
It was during our stay at South Seas that we had our first good dolphin siting—an entire pod, in fact, chasing down breakfast just off the fishing dock on the edge of Redfish Pass, a deep, but narrow channel leading out to the Gulf. 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 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 of hundred yards. The marina is home to a substantial charter fishing fleet, countless herons and egrets, and yet another healthy troop of manatees. I only wish we’d had the time to take a kayak across the anchorage to explore the mangroves ringing nearby Buck Key.
A Drag Race Home
The next morning we cast off lines early in an effort to beat a weather front coming in from the north. The forecast was for strong southerlies clocking into the southwest, which would have been perfect for our passage: about eight miles almost due north along the ICW, then another seven or so miles east-northeast across Charlotte Harbor back to Burnt Store.
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—the latter reportedly served as the inspiration for Jimmy Buffet’s “Cheeseburger in Paradise”—we rolled in a bit of our headsail to make the gybes 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 more in her element, 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 into the west, so we now found ourselves sailing on a beam 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.
Still, everyone did their best, hunkering down behind the dodger out of the spray and making the most of what we dubbed the “challenging” end to our brief voyage. Of course, as soon as we came within the lee of the twin islands guarding the entrance to the channel at Burnt Store, everything 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 in Southwest Florida.