Sanibel & Captiva: The Easiest Vacation in America

A week on Florida’s Sanibel and Captiva islands is guaranteed smooth sailing—even when you’re traveling with a persnickety eight-year-old dubbed Captain Picky.

A fundamental axiom of the Family Vacation holds that if the kids have a good time, then the vacation is a success. This is more or less true, and yet, if you’re a parent, it’s also a little” pathetic. Because it means that your own enjoyment of a place is simply a by-product of your child’s. That’s a perilous emotional logic, for where it usually leads, as swiftly and inexorably as a water slide, is to yet another week at Disney World.

Not that the obvious alternative is anything to get excited about: dragging the kids, I mean, to Sites of Significant Cultural or Natural Interest, a high-friction slog that can leave you savoring the tranquility of that first Monday back at the office. Factor in a child such as Isaac—a somewhat quirky, none-too-flexible eight-year-old who objects on principle to doing/eating/experiencing anything he hasn’t done/eaten/experienced in the past—and this sort of vacation quickly becomes more work than work. The last time I told Isaac we were thinking of going somewhere new, he gave me a look of genuine pity. “Remember, Dad,” he said, bouncing his thumb off his chest, “this is Captain Picky.”

Judith and I had all but decided to shelve family travel for the foreseeable future when a friend suggested we check out Sanibel and Captiva islands, on Florida’s Gulf Coast, which he claimed in no uncertain terms constituted “the easiest family vacation in America.” I was skeptical, not just because I associate Florida with too much development and too many early-bird specials, but because I couldn’t believe a place that was “easy” could also be interesting. I was wrong. Somehow, Sanibel Island manages to be both.

The easy part first. The grooves of a vacation week on Sanibel are well-worn but agreeably smooth: Rent a two-bedroom condo on the beach (you can tour hundreds of units on the brokers’ Web sites [see The Facts]); fly in on a Saturday (when the leases all start); stock up on everything you’ll need (fresh fish, groceries, wine, beer, beach reads, sunblock) at Jerry’s; rent bikes first thing Sunday morning; and settle in. Sure, you can go wild—stay at a resort instead, eat out every night, arrive on a Tuesday—but this is one case in which conformity to custom has its rewards.

Sanibel and its smaller, narrower sister island, Captiva, form a slightly bent arm of sand reaching up from the Gulf Coast off Fort Myers, where the arm is joined to the mainland by a causeway. The causeway wasn’t built until 1963, so up to that point the islands were spared the thoughtless high-rise development that has wrecked so much of the Florida coast. By the time the causeway opened the floodgates, visionary land-use controls had been put in place. Fully two-thirds of Sanibel has been declared off-limits to development and left in its natural state: mostly spartina grass in the highlands and mangrove swamp in the low. Along the beach no building may exceed the height of a palm. Today the island’s gulf coast wears a long white necklace of low-rise condos, most of them invisible from the shore road, carefully folded into groves of stately palm and feathery Australian pine.

Your typical Sanibel condo complex consists of a trio of three-story buildings around a pool and is connected to the beach by a narrow boardwalk on stilts, to protect the fragile dunes. What the individual units lack in distinctiveness or charm—picture coral carpeting, Kmart wicker, and every seashell tchotchke known to man—they more than make up for in spaciousness, convenience, and water views.

In the company of Captain Picky, eating dinner out is seldom a treat. (C.P. is even finicky about McDonald’s, preferring the cuisine at certain higher-volume outlets to that at others.) For us, being able to cook dinner ourselves is a boon, especially when there are communal gas-fired Webers by the pool, and a screened terrace with a nightly view of a fiery sun capsizing into the pale blue gulf. So while the Captain picked at his pasta cooked just so, Judith and I ate grilled fish or shrimp in a setting to rival any island restaurant’s.

An important corollary to the axiom of the Family Vacation is that if the kids can meet other kids early on, everyone benefits. This is almost guaranteed to happen here—the scale and layout of Sanibel’s condo complexes are just right for fostering a marvelous sense of community. (The fact that everyone arrives and departs on the same day contributes to the instant-community effect.) By midweek Isaac’s new buddies, Soren, 7, and Ingrid, 11, from Iowa, had been over for dinner and out for miniature golf, and he’d spent a cloudy afternoon at their condo making seashell refrigerator magnets. (The shell motif is inescapable.)

There’s probably an optimal number of families around the pool to facilitate not only kids striking up friendships but also their parents getting well enough acquainted to keep an eye on one another’s broods. (A minimum of six families, I’d venture, max of 10.) By Tuesday the dads were taking turns in the pool playing with the gang of kids (a blessing, because when you’re off duty you can actually read your book with both eyes), and before long kids were running in and out of our various units in search of the best-stocked fridge, like some sweet dream of suburbia circa 1962.

In fact, Captain Picky found condo life so much to his liking that he never wanted to leave the grounds, which posed a problem for his parents. The easy part of a week on Sanibel threatened to cancel out the interesting parts, most of which lie beyond the condo gates. There is, for instance, the beach, a spectacular strand of sugary sand that runs the length of the island and offers some of the best shelling in the world. (From dawn to dusk you see people doubled over in “the Sanibel stoop,” as if an entire society had simultaneously lost their contact lenses.) Captain Picky felt that the shells on sale in the shops were far superior to the ones on the beach (true enough), so what exactly was the point? Birding, another excellent Sanibel diversion, struck him as equally purposeless, and Isaac isn’t yet good enough at biking to really enjoy it.

So the first few days, Judith and I took turns exploring the island by bicycle, without a doubt one of the most exhilarating pleasures it has to offer—and perhaps the ultimate Sanibel marriage of easy and interesting. Easy because the island’s bike paths are so well maintained and flat that you don’t need to shift gears or even be in shape, and interesting because the landscape is so captivating. Twenty minutes after leaving Condo World I was deep within the J. N. “Ding” Darling National Wildlife Refuge, riding along dikes that bisect broad plains of still water fringed with mangroves. Prehistoric-looking birds on improbably tall stilts patrol the mirrored waters, which are flustered every now and then by the silver flash of a mullet.

I found the areas outside Sanibel’s nature preserves just as striking. The island is divided into two sovereign kingdoms, Nature and Civilization, making it a place of startling frontiers. In the very same frame, you can watch a poodle romping on a manicured lawn and an alligator sunning itself on a mudbank. Somehow, it works: the unreconstructed, swampy wild appears to be thriving in the very shadow of Condo World. (Somehow, too, there seemed to be virtually no bugs.)

While biking around the island, wondering about how I might entice Isaac away from the pool and into this landscape, I hit on an idea. One thing Captain Picky does like is games—we’d organize a Sanibel Island treasure hunt for Isaac and his pals. So I drew up a list of a dozen creatures, plants, and shells likely to be findable on the beach, at “Ding” Darling, or just while walking around: lizard; alligator; snowy egret; saw palmetto; bromeliad; roseate spoonbill; fighting conch shell; banded tulip shell; oyster shell; tortoise or turtle; osprey; sand dollar. Judith, a painter, made simple sketches to illustrate each one. Whoever ticked off all the boxes on the checklist first would win the (under $5) souvenir of his or her choice.

Suddenly “Ding” Darling was no longer “a boring old swamp” but a vast storehouse of potential points, and Isaac and Soren couldn’t wait to go. It was low tide when we arrived, and right away we spotted through our car window a flock of roseate spoonbills—an awkward, pink, Dr. Seussian shorebird—snagging minnows in the shallows. Later we spied a saw palmetto, and a pair of adolescent alligators snoozing in the mud. Captain Picky’s competitive instinct now fired, he drew me aside to ask if we might get up early the next morning to go shelling on the beach before his opponent was awake.

For the rest of the week, Isaac was eager to venture out beyond Condo World, bringing his checklist and eagle eye everywhere we went. Hoping perhaps to knock off a few more boxes, he joined us on a water tour of “Ding” Darling, which turned out to be a high point of our week. Following a blond naturalist-dude, a dozen of us in one- and two-person kayaks paddled deep into the mangrove forest, tracing a web of water trails through one of the weirdest, most beautiful places I’ve ever seen. The canopy of trees closes overhead, forming cool, shadowy tunnels walled in by extravagantly contorted roots crusted with oysters (check!) and barnacles. Because the black water was so still, Isaac and I went several miles with ease, adding egrets and bromeliads to his checklist, not to mention an Actual New Experience to the heretofore rather thin official Captain Picky biography. Unfolding our legs from the kayak after three hours, we both felt a sense of triumph.

AFTER A WEEK ON SANIBEL WE PULLED UP stakes and made the half-hour drive north, crossing the two-lane bridge onto Captiva and entering a very different world. Captiva is a six-mile-long finger of land lined with powdery white beaches and, in place of condos, grand houses, many of them rentable by the week. Occupying the entire northern third is the sprawling South Seas Resort, where we spent our last couple of days.

It’s a pleasant walk from the resort to the town of Captiva, a compact district of restaurants and shops that is funkier than the commercial strip on Sanibel. Andy Rosse Lane, the main street, runs right to the beach—and to the Mucky Duck, a legendary English pub where, at sunset, adults sip ale at picnic tables while kids play ringtoss beneath a towering pine.

But there’s tons to do without ever leaving the 330-acre resort—from shuffleboard and fishing to parasailing, waterskiing, and sailing, to golf and tennis and crafts and swimming, either in 18 pools or off two miles of blindingly white beach. The resort’s trolley means older kids can get around on their own. They can also charge ice cream cones on their folks’ South Seas credit cards and put together their own Good Time from the kit of parts the resort offers them. For a teen or preteen, I imagine, the South Seas Resort would be as much a utopia as Condo World was for Captain P.’s younger set.

Eager to break out of the somewhat bland bubble of the resort, on our last afternoon we chartered a motorboat and set out to explore the unpeopled islands to Captiva’s north. Our second adventure-by-water wound up being easily as memorable as the first. Our captain, Brian Holaway, not only knows the local waters intimately, but is also up on botany, shells, birds, fish, geology, history, archaeology, and Indian lore; plus, he has a deft touch with kids. As we motored north toward Cayo Costa—where the shelling was unrivaled, we’d heard (by now we too were hooked)—the boat threaded its way through go-slow manatee zones, between pods of arcing dolphins, and past great blue herons fishing intently in the tidal flats. After a half-hour ride, Brian tied up at a rickety dock on Cayo Costa, a paring of pristine land that’s a state park. We crossed the pencil-thin island on a boardwalk raised above a shadowy mangrove swamp. Within minutes the boardwalk abruptly ended in a breathtaking crescent of beach we had all to ourselves. Isaac and I went for a swim, joined by a trio of dolphins drawing lazy loops in the water with their dorsal fins no more than 30 yards away.

The shelling was good if not quite as spectacular as advertised, but with help from Brian, Isaac managed to complete his checklist: together they found an intact sand dollar and a piece of a sea turtle’s shell that the contest judge (i.e., me) ruled acceptable. By the end of the afternoon, Captains Picky and Holaway were fast friends, and Isaac had learned not only how the Calusa Indians made rope from palm fronds, but, for the first time in his life, about some of the pleasures of the new, which is to say, of travel.



Bailey-Matthews Shell Museum 3075 Sanibel-Captiva Rd.; 941/395-2233. “They have a treasure hunt for kids, and you can pick a shell to take home. But the slide show is bor-ing.” Mona Lisa’s Pizza 2440 Palm Ridge Rd.; 941/472-0212. “Really good pizza. And there’s a TV showing the Cartoon Network, but no sound.” Three Crafty Ladies 1620 Periwinkle Way; 941/472-2893. “This is where to get the magnets and glue to make shell magnets.” Butterfly House Sanibel-Captiva Conservation Foundation’s Nature Center, 3333 Sanibel-Captiva Rd.; 941/472-2329. “You go inside a big tent and butterflies land on your head.” Pinocchio’s 362 Periwinkle Way; 941/472-6566. “There’s a lot of good ice cream on Sanibel, but this is my favorite. The sundaes are immense.” Tuttles 362 Periwinkle Way; 941/472-0707. “Baskets with shells and stuff for under a dollar. I got a shark-tooth necklace.” Castle Golf 7400 Gladiolus Dr., Fort Myers; 941/489-1999. “Awesome miniature golf, with tons of water features. We go on our way to the airport.”


Several real estate brokers handle weekly rentals of condos and houses on both islands; find their links at, the Lee Island Coast Visitor & Convention Bureau’s Web site (or call 888/231-6933). Rates fluctuate, depending on the season (mid-January to April is peak). During school vacation weeks, expect to pay $2,000 to $3,000 for a two-bedroom beach condo, half that in the off-season. Rentals are Saturday to Saturday and include linens. Housekeeping and baby-sitting services are often available through your broker, who is also a good person to ask about restaurants and boat charters.


Billy’s Rentals 1470 Periwinkle Way; 941/472-5248; bikes from $35 a week. You can rent all manner of bicycles (and kid attachments) by the hour, day, or week, but don’t bother going for anything fancy: there are no hills ahead. Free delivery.

Jerry’s Foods 1700 Periwinkle Way; 941/472-9300. Grocery with a good bakery and extensive wine selection.

Bowman’s Beach Off Sanibel-Captiva Rd. Should you tire of your condo’s pool and beach, take a drive to what’s considered Sanibel’s most gorgeous stretch of sand.

Gramma Dot’s 634 N. Yachtsman Dr., Sanibel Marina; 941/472-8138. Standout seafood and salads, served dockside.

J. N. “Ding” Darling National Wildlife Refuge 1 Wildlife Dr.; 941/472-1100; closed to cars Fridays. Though most people go to the main refuge on Sanibel-Captiva Road — best at low tide, when the shorebirds feed — the smaller Bailey Tract, 100 acres of spartina grasses and marshes, is worth a visit. And you’ll have the place to yourself.

Lighthouse Café 362 Periwinkle Way; 941/472-0303. Terrific fruit pancakes and fish sandwiches at this popular breakfast and lunch spot (and we mean popular — expect to wait at least 30 minutes for a table).

Tarpon Bay Recreation 900 Tarpon Bay Rd.; 941/472-8900;; guided kayak and canoe tours $25 for adults, $12.50 for children under 12. Rent canoes and kayaks for fishing or exploring “Ding” Darling, on your own or with their knowledgeable guides.


Captain Brian on the Water; 239-989-6522;; $450 for an excursion of at least 4 hours. Motorboat charters with Captain Brian Holaway. [Prices and contact information updated in Spring 2016].

Bubble Room 15001 Captiva Dr.; 941/472-5558. A cartoony warren of rooms jam-packed with vintage toys, trains, and Hollywood memorabilia. Some people swear by the food, but I make it a point not to eat in any restaurant with a gift shop and a two-hour wait.

Mucky Duck 11546 Andy Rosse Lane; 941/472-3434. Be sure to have at least a beer here at sunset. And they do serve duck.

R. C. Otter’s 11506 Andy Rosse Lane; 941/395-1142. Casual place for breakfast, lunch, or dinner. Fried fish, shrimp, salads, microbrews, and kids’ fare.

South Seas Resort 5400 Captiva Rd.; 800/227-8482 or 941/472-5111;; doubles from $145, two-bedroom cottages from $365, kids under 16 free.