Southwest Florida is one of my favorite cruising areas, especially in early November when the Chesapeake Bay is starting to get chilly and Lake Huron’s North Channel is just plain miserable. The winds have shaken off the summer doldrums, the temperature is in the mid to upper 70s, and anchorages and marinas are not yet crowded with winter visitors. In short, it’s the ideal time and place for a week’s charter vacation.
Headquartered at Burnt Store Marina near Fort Myers, Southwest Florida Yacht Charters (SFYC) is conveniently located in the center of one of the South’s finest cruising grounds. Going north, you can cruise 60 miles to Tampa Bay, and visit Venice, Sarasota and Bradenton if you’re feeling ambitious. Going south, Naples is about 60 miles away. To the west, you have Fort Myers and the Caloosahatchee River.
Depending on the kind of sailing you want to do, you can stay safely inside the barrier islands of Charlotte Harbor and Pine Island Sound, or go offshore into the Gulf of Mexico. Ultimately, the toughest part of setting out is choosing which of these destinations you want to explore.
In addition to singing the praises of all the best spots in these different areas, Mark, the SFYC manager, also gave me a detailed tour of the 34ft Gemini 105 catamaran I chartered from him. A good briefing denotes a superior charter company: any unfamiliar boat has its quirks, and knowing these in advance ensures a better cruise. The same goes for the chart briefing: better to know where the problem spots are in advance than to find them on your own.
After talking things over with Mark, I decided my crew (a stray puppy I adopted last winter while sailing in Cuba) would have the best time if we stayed safely inside the sheltered waters of Charlotte Harbor. Although I’m not a big fan of catamarans, I chose to charter the Gemini 105 because I knew its shallow draft would give me more freedom in this sort of area. It’s a roomy boat, well set up for cruising, and is nicely appointed. Small wonder it’s so popular with both owners and charterers.
After shucking my northern gear for shorts and a T-shirt, i headed out and quickly raised the main and jib in a 10-knot breeze. Then I killed the engine and enjoyed a quiet sail while the pup explored the cockpit. My destination for the evening was Boca Grande Marina, on Gasparilla Island. This put the wind nicely on the quarter for a cruising speed of about 5 knots. The charts showed there was nothing to worry about during the 10-mile trip, so I engaged the autopilot and leaned back in the cockpit to enjoy the sunshine. Ahh...
Charlotte Harbor and Pine island Sound are protected from the gulf of Mexico by a series of outlying islands, including Gasparilla, Cayo Costa, Sanibel and Captiva. These shelter a large cruising area with numerous protected anchorages among the many smaller cays. The Intracoastal Waterway also winds through here, so you often see cruisers from distant shores exploring the region. It’s a pretty area, with plenty of room to sail no matter what the wind direction.
Arriving at Boca Grande Harbor, i saw a number of boats Med-moored with their sterns tied to the mangroves to the north. It’s well protected in there, but i knew the mosquitoes could be terrible, coming at you in armadas, and was glad to be staying at the marina.
Boca Grande Marina’s dockmaster came down herself to make sure my Gemini was quickly and properly tied off by her staff. She also filled me in on the area’s attractions. I immediately commandeered a golf cart and headed over to the far side of the island to watch the sunset, joining several others who had the same idea. One couple, down from Ohio, were just a couple of years away from cruising their own boat south and were full of questions about the lifestyle.
Back at the marina, the restaurant was crowded with locals, always a good sign, so I went out to the deck for a meal and a cold beverage. The folks at the next table were celebrating an 80th birthday in a lively way and shared their fun with all around them. After a lot of laughter—and many toasts—I returned to the boat mulling on how good life is, no matter how young or old you happen to be.
The next leg of my voyage was all of six miles across Boca Grande Pass over to Cabbage Key for a late lunch; late, because I wanted to miss the tourist boats with their crowds and noise, and was also enjoying another leisurely sail. Although I could have tied up at the Cabbage Key dock, I chose instead to anchor on the other side of the ICW and dinghy over.
Cabbage Key is accessible only by water. The former residence of mystery writer Mary Reinhart, it offers excellent burgers, and the beer is icy cold, so it’s a mandatory stop for many. The first thing you notice when you arrive in the bar are the thousands of dollar bills tacked to the walls, ceilings and pretty much every other available surface. The waiter told me these totaled about $70,000. Every year Cabbage Key donates $10,000 to 12,000 of this money to the Southwest Florida Marine Institute, a school for troubled children.
On the way back to the dinghy, my puppy spotted two gopher tortoises and raced over to investigate, much to their consternation. Many of the guests feed them lettuce, and they are a great hit with both kids and adults.
Back at the boat, I debated whether I should walk the island’s nature trail, which is reputed to be very good, or take a short nap back on the boat before sailing 11 miles further to Captiva Island. I fell asleep during the debate and woke to see the sun leaning well toward the horizon (it couldn’t have been the beer!) and realized the last several miles to Captiva would have to be done in the dark. This concerned me, because although I’d been to Tween Waters Marina before, Roosevelt Channel is narrow, somewhat winding and very shoal. It wasn’t the kind of place I wanted to be at night, especially now that the wind had increased to 15 to 20 knots—on the nose, of course.
I set out anyway and soon found the short passage was more than a little challenging, particularly as none of the channel markers were lit. I wondered several times if it might not be wiser to anchor out, as opposed to going into the marina, but made it in without incident. Of course, no sooner had I finished tying up than a local party boat came up the channel, lights glaring, music blaring, clearly showing the way in. Had I been just 10 minutes later, I could have followed it in with no stress whatsoever. I couldn’t help wondering, as all sailors no doubt do in similar situations, why things always seem to turn out this way.
Tween Waters is just across the road from the Gulf of Mexico, with superb beaches for walking and shell collecting. There is also a large pool, pub, three restaurants and the usual resort amenities. There is no landing ashore, however, for those who choose to anchor out.
The Return Trip
From Captiva, I traced my route back toward Cabbage Key, heading first for the bight in Punta Blanca. The wind had now shifted into the northwest, and I worked hard to keep the boat close hauled—catamarans are notoriously poor sailing on the wind, at best. When I lowered the Gemini’s leeward centerboard, it improved the boat’s tracking, but the channel ultimately turned too close to the wind, and I had no choice but to douse the sails. Still, it was fun while it lasted. In this area, the wind is often strong, but you get no real waves, which makes for fast, flat sailing.
The bight in Punta Blanca is a well-protected spot surrounded by mangroves. I’ve sat there in a 30-knot norther with not a ripple on the water. The trick is getting in, as the channel isn’t marked.
The next morning, on Mark’s suggestion, I decided to check out the Pelican Bay anchorage between Cayo Costa and Punta Blanca. It was wonderful, but exposed to the north and northeast, which would have made it uncomfortable the evening before. Cayo Costa State Park offers day and some overnight dockage for those wishing to explore, and there’s a lovely secluded beach by the pass. The park is an excellent location for those with a family on board, with a tram to take the kids over to the Gulf beaches.
The last night of my charter I stayed at Useppa Island, a private island and marina that clients of Southwestern Florida Yacht Charters are permitted to visit. This turned out to be the highlight of my cruise and would have justified the cost of the charter all on its own. The island is magnificent, with beautiful island homes connected by a series of roads and pathways, all exquisitely landscaped. Its museum is equally fascinating. Did you know Useppa once served as a training base for the Bay of Pigs invasion? For variety, there are tournament quality croquet courts and the largest (and only) outdoor chess board I’ve ever seen.
Given the island’s exclusivity, I was concerned about dinner at the Collier Inn fitting into my budget. How wrong I was. The food was superb and no more expensive than at any good roadside pub. My only regret was not being able to stay for the Friday night happy hour at the Tarpon Bar. There’s something about being in a millionaire’s paradise while drinking $2 draught beer that appeals to my sense of irony.
The following day, I lingered as long as I could, knowing I might never get to visit Useppa Island again, given my lack of wealthy elderly maiden aunts. I was also hoping the wind, which had shifted east, would moderate for an easier ride home.
No such luck. My final few hours were a painful slog into a headwind and short nasty chop, which slowed the boat considerably. Raising sail to ease the pain wasn’t even a consideration, as I’d left myself too little time to tack across the bay.
My last night at the Southwestern Florida Yacht Charters base was a contemplative one. I’d anchored in beautiful rustic locations with no one about, hung out in some nice marinas with great facilities, explored an interesting small town and visited one of America’s most exclusive islands. It had been a smorgasbord of different impressions, all of them wonderfully tasty; a smorgasbord that I hope to someday enjoy again.