Sailing in Villas

Select Local Merchants

It only took two weeks on the picturesque shores of Tahiti and Moorea to send Craig Stewart into a tailspin. He and wife Evelyn fell in love with the South Pacific’s crystalline waters and beachy breezes, so much so that the prospect of remaining in their native Oklahoma turned gloomy. Six years after the Stewarts’ Pacific vacation, they stumbled upon Sanibel Island. With a love for the waters still coursing through their veins, they uprooted and moved there, making it home base for Adventures in Paradise. In 1986, they started out with one boat—Miss Paradise—and one tour, the sunset dolphin cruise. Today, the Stewart family maintains a much larger operation. Their tour topics range from fishing and shelling to dolphin watching to historical sightseeing on a trolley.

14341 Port Comfort Rd.
Fort Myers,
FL
US

Mid Island Water Sports set up shop along the aqua shorelines of Ostego Bay to give everyone easy access to the Gulf, while also giving them enough room to ride free. From two locations, the crew hooks up aquatic adventurers with WaveRunners for freestyle rides along sandy beaches in one of the largest riding areas in the Gulf. Longtime locals lead tours via WaveRunner to spot dolphins breaking the sea's surface and manatees playing with sea kittens. To give locals and visitors an exhilarating new way to take in the Gulf's scenic vistas, the shop's US Coast Guard?certified captain sends them soaring behind him during parasail rides tethered to his high-tech, winch-style parasail boat for an adventuresome trip along the south end of Fort Myers Beach.

5550 Estero Boulevard
Fort Myers Beach,
FL
US

Pirates cheer as cannons fire smoke across the sea. Yet while the pirates are actors and the cannons are just miniaturized toys, the ship they sail upon is anything but pretend—it's a 65-foot steel-hulled vessel designed by a naval architect to look like a Spanish galleon.

Named for the prized Spanish currency of yore, Pieces of Eight Pirate Cruise evokes the golden age of buccaneering as it sets sail from Salty Sam’s Marina. The ship is helmed by a merry band of pirates—such as Pick Pocket Pete, Peg Leg Meg, and Fancy Face Phil—that bookends lessons on pirate history with sing-along chanteys and skits. The 90-minute family-friendly cruise also includes map-reading trivia, face painting, yo-ho-ho, and a bottle of rum. During the ride, passengers are welcome to explore the upper and lower decks or step inside the grand salon for ice cream, pretzels, and other treats.

In addition to its all-ages cruises, Pieces of Eight hosts an adults-only cruise on Friday nights, which includes cocktails and its own revue. It also charters private cruises to celebrate birthdays and other special occasions.

2500 Main St
Fort Myers Beach,
FL
US

From a distance, the manatees, dolphins, and bald eagles that populate Estero Island make quite an impression. But the staff at Holiday Water Sports of Fort Myers Beach believes up-close encounters are not only the sole way to determine if the animals can talk, but also the best way to enjoy them. To that end, they guide tours and rent out myriad watercraft, from Yamaha 4 waverunners and 10-passenger pontoon boats to paddle bikes, which resemble oversized tricycles as they surge through nimbuses of sea foam. The staff hoists parasailers over their water-bound peers, letting out up to 1,200 feet of slack and allowing riders to plunge into free falls with houses and piers blurring into a cubist painting beneath them. Captains certified by the United States Coast Guard guide the ships back toward the sun-bleached sands, where the company’s rental umbrellas rustle in the breeze above lounge chairs.

200 Estero Boulevard
Fort Myers Beach,
FL
US

With a stable of two schooners, Appledore IV and Appledore V, which split their time between Fort Myers, Florida, and Bay City and Mackinaw City, Michigan, BaySail's captains ferry passengers about the Great Lakes and the Gulf of Mexico during leisurely and educational tours. The sea vessels depart from Bay City to wind along the Saginaw River and into open water, letting passengers soak up summer sun or, in the autumn, traveling upriver for spectacular views of changing leaves and scarecrows playing hooky on the riverbanks. Come winter, the Appledore V makes its way to Florida, where it seeks out the dolphin populations of San Carlos Bay. All of BaySail's excursions are interactive seafaring affairs in which passengers are encouraged to help to crew the watercraft, learn about fish brought into onboard tanks, and force seagulls to walk the plank.

2500 Main Street
Fort Myers Beach,
FL
US

The gentle clap of paddles against the water and the tenor thrumming of jet-ski motors drift from Adventure Water Sports. On waverunners, diminutive sailboats, and kayaks, patrons spread out across the surf and around Estero Island, their eyes peeled for dolphins and other fauna at all times. The shoreline falls back in quiet bays and estuaries, where little fish dart among tangled knots of mangrove roots. Instructors certified by the United States Coast Guard demonstrate the operation of vessels, lead tours, and knock down sand castles lacking proper fire exits.

1160 Estero Boulevard
Fort Myers Beach,
FL
US