We’re all hoping to find charter areas that are overlooked, if only to get away from crowded anchorages, crowded restaurants, crowded pubs and, frankly, the crowds themselves.

I have one for you, with white sand beaches as soft as powdered sugar, warm waters, mild trade winds, flat seas, plenty of sunshine and more great marinas and resorts than you’ll have time to explore in a week-long charter. Choose between nearly empty anchorages and marinas with every possible amenity from shore power and drinkable water to playgrounds for the kids.

Perhaps best of all, there are no long waits in airport TSA lines, no layovers to board inter-island puddlejumpers, no lost luggage. You can do your provisioning, not at a rob-all tiny grocery near a charter base, but at an inexpensive “big box” like Costco or Sam’s Club. You don’t need a visa or even a passport, credit cards are accepted with delight, and the natives all speak English, more or less. 

It’s an easy drive from much of America, so you can pile as much luggage, water toys and your necessities (from shampoo to galley seasonings) as your car will hold. 

Think western Florida. Pine Island Sound, specifically. Located close to Ft. Myers, you probably know it for the islands of Sanibel and Captiva. It’s south of Tampa and St. Petersburg, north of the Florida Keys. 

It is quite perfect. And it seems like it’s a thousand miles away.

Our Pine Island Sound bareboating adventure started with Southwest Florida Yacht Charters in Cape Coral, Florida, which is in the heart of Pine Island Sound, so you’re in the charter area within a couple of hours of casting off the dock lines.

SWFYC is celebrating its 40th year in business, in no small part because it is a family owned business with Barb and Vic Hansen overseeing even the tiniest details. We’ve chartered several boats from them, and each has been pristine, with no mechanical issues of any sort. 

That said, SWFYC also survived a trashing from Hurricane Ian, the 2022 deadly and destructive category 5 hurricane with winds up to 160 mph. Not only were the company’s boats gone, but so were the docks and infrastructure that made the area so delightful.

The good news is that SWFYC has rebounded, along with the many resorts and marinas in the area. Our charter was aboard a Leopard 38, which has been replaced in their fleet with an even-better Leopard 40 sailing cat. 

For those who might not know Leopards, these cats have acres of inside space, large cockpit and foredeck areas and, unlike some big cats, are actually fun to sail. 

Like the 40, our Leopard was the three-stateroom layout and, being the captain, I promptly staked out the starboard cabin, which fills that entire hull. A larger-than-queen-sized berth is aft, with hanging lockers, bureau and vanity amidships. Forward is a truly capacious head with a stall shower (save water and shower with friends!). Two more staterooms, the after with another queen-plus berth and another head with stall shower.

She Who Must Be Obeyed gravitated immediately to the galley, with lots of counter space, fridge and freezer drawers, a three-burner gas cooktop, and tons of both view and ventilation (a front door). The saloon has an L-shaped dinette which is under the air conditioning, or you can open the full-width sliders to the cockpit and an even larger dinette.

While she checked out the chef zone, I stepped up to the raised office for the skipper, which is a direct step onto the side deck in case one of the crew needed my wisdom with dock lines or fenders. The helm is ever so tidy, with all the lines (furlers, halyards and sheets) led aft to the helm where stoppers and a big winch make sailing effortless. The dash had a complement of Raymarine electronics including a chartplotter that Pine Island Sound newbies will get to know intimately. 

Nights were secure with a 45-pound Delta anchor (perfect for these bottoms) with an electric windlass tucked under a hatch forward. Speaking of nights, the Northern Lights 6-kilowatt generator easily handled the dual air conditioning as well as keeping the blender punching out piña coladas.

Enough about the boat, we were anxious to get underway, and our checkout was thorough and knowledgeable on everything from the location of the breakers to where we could find the best burgers. And something I find delightful in a bareboat: a library with manuals for every piece of gear aboard. Got a question? Just look it up.

The SWFYC base is on the Caloosahatchee River (say that three times fast) and, since the day was getting late after stashing provisions, we ducked around the corner to the marina at the Marriott Sanibel Harbour Resort and Spa. I told the crew the name of the property, but I intentionally softened the last word.

No such luck. The girls instantly spotted the quite luxurious spa at this resort and suggested that we should “check the anchor gear” while they disappeared behind the Far East-inspired spa doors. I can say with complete confidence that the following words have never appeared on the pages of SAILING Magazine: “Glorified Foot Massage,” “Glow on the Go Facial” or “Sanibel Pedicure,” but I am also assured that at least half of the bareboaters reading this story will find this to be useful information.

In defense, I can assure the other half of the readership that the Courtside Steakhouse, just steps from our marina berth, has a Grand Island ribeye, with cognac cream and peppercorn au poivre sauce, that is hugely better than any slab of beef I would prepare on the propane stern grill on our boat.

The next morning was our introduction to the Wonderful Wacky World of Intracoastal buoyage. The crew at SWFYC had tipped us off that “red-right-returning-to-Texas” was a mnemonic that not only made sense, but saved those of us used to the “red-right-returning” for coastal navigation. 

A second nav tip was that “white is all right, blue review.” Take a look at the chart book (provided) or the chartplotter, and you’ll see that white means deep water, blue not so much.

To that I would add a simpler rule: “Don’t go where the birds are standing.” These are thin waters and I don’t remember seeing anything over 10 feet under our bottom, so I cranked the chartplotter up to its largest scale when we were tiptoeing into harbors. The good news, however, is that the bottom is generally soft mud (hence the Delta anchor). I would add one essential piece of equipment: a good pair of Polaroid sunglasses can make shallows pop into vision.

Once you overcome your fear of the blue zones, Pine Island Sound, its islands, and nearby Charlotte Harbor have a multitude of places to explore and overnight. 

Our first morning was spent frolicking in the warm waters at Picnic Island, which has a curving beach and inner lagoon. Tip: Get there early, because this is a popular destination for sportboats blasting over from the mainland. 

Not long after, we found ourselves escorted by a trio of dolphins which amused themselves (and us) by playing in our bow wave. Later, we found that we weren’t alone: these unofficial greeters love to perform for boats.

A close reach took us past the Ding Darling National Wildlife Refuge on Sanibel, which is the largest mangrove ecosystem in the U.S., and birdwatchers will revel in more than 200 species of birds, including bald eagles.

Still getting used to the boat, our goal for the first night was at ‘Tween Waters Inn, a folksy resort that’s been a mainstay since the 1920s. Amazingly, it took only minor bumps and bruises from Ian, and we had 30-amp power and freshwater at our dock. If we sound like the old maxim that “an army travels on its stomach,” well, yes, we do. SWMBO is a spectacular chef with a couple of French restaurants on her CV, and I may be the resident beef-eater, but I was outvoted in favor of The Shipyard on the ‘Tween Waters grounds. My counsel? Don’t miss the South Carolina crab soup, the ribs with homemade bacon/caramelized onion sauce, or the grilled grouper with piña colada butter.

We decided we couldn’t possibly spend every night in a marina, so we opted for an unnamed bight (SWFYC recommended) to drop the hook for the night. Our 10-foot tender was launched to explore the mangroves, which are dense and filled with birds. We left the tender in the water (it retrieves easily with an electric winch and a clever davit system) to protect it from our grill, which produced a feast of burgers, hot dogs, and grilled veggies.

I had expected our anchorage to be dark, but I was wrong. It was a clear night, and the dome of stars overhead made me rue not bringing my starfinder chart. It was a little more humid near the mangroves, so air conditioning went on and doors closed. We slept hard.

Another lovely reach on flat water, with enough tradewinds to encourage our Leopard to kick up her heels, took us to South Seas Island Resort, which is still rebuilding after a direct hit from Ian. The yacht harbor is back, with good dockage, water and electricity. During the process of recovering their several fine restaurants South Seas had the clever idea of bringing in food trucks, which our crew embraced wholeheartedly. At the Shell City Burgers truck, you need to try the Shell City Crabcake Burger with onion rings served with their “secret” Smash sauce. Hit the Island Tacos truck for the shrimp ceviche in a cocktail glass. 

One particular delight of South Seas Island Resort is that you can walk across the street to the beautiful two-and-a-half-mile beach. You might want to swim, but it’s more likely you’ll be gobsmacked by the incredible shells just lying about on the beach. 

Our next sail brought the weird moment of our charter. We headed for the protection of Cayo Costa, a barrier island, and tucked in to Cabbage Key, where Jimmy Buffett is said to have been inspired to write “Cheeseburger in Paradise.” Yes, dozens of restaurants claim that title, but I’ll award Cabbage Key with the crown. 

But that wasn’t the weirdness. Cabbage Key was once the home of mystery writer Mary Roberts Rinehart, and it has the “most expensive wallpaper in the world.” The Cabbage Key bar, with nearly 100-year-old floors and fireplace, is papered with thousands upon thousands of autographed dollar bills. My best guesstimate of the amount of bills hanging there is probably between $40,000 and $50,000. The cool part is that the owners gather up loose or falling bills and, when they reach $10,000, donate them to a local charity. 

We chose to eat the Buffett Burgers and depart, heading for nearby Useppa Island, a private island that allows only golf carts for transport. Charterers from SWFYC can enjoy their fine marina, since the Hansens are members. Want to anchor out? The tip of Cayo Costa has Pelican Bay, a favorite for cruising skippers as a quiet anchorage.

With great regrets, not to mention bags of seashells, we turned our bows south to return to civilization. We’d had great meals, we’d mixed quiet anchorages with pleasant marinas, dinners aboard under the stars with great restaurants. 

We had a great yacht, an attentive charter company, and a wonderfully undiscovered cruising area. It was almost too easy to be this delightful.