Sailing in Cape Coral

Select Local Merchants

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

Tarpon Bay Explorers furnishes adventurers with sturdy kayaks, canoes, bikes, and pontoon boats for embarking on warm-weather escapades. Paddle away for two hours of solo or buddy-enhanced exploration through the meandering tributaries and aquatic expanses of Tarpon Bay and the mangrove-lined Commodore Creek Water Trail. Marine life abounds in the coastal watery wilderness, where skippers can expect to spot dolphins, manatees, sea birds, lightly slumbering Poseidons and more. Two-person kayak passengers also enjoy the buoyant benefits of the included flotation vests, guarding against the lure of chic underwater dance clubs.

900 Tarpon Bay Rd
Sanibel,
FL
US

It's the southernmost point of the entire United States, approximately 95 miles north of Cuba with a longitude of relaxation and a latitude of party time. Key West is the place where Ernest Hemingway and Tennessee Williams worked on their tans and perhaps wrote some novels, and where Ponce de Leon searched for his fountain of youth. Since people still haven't evolved to grow wings, they often try to get there via the Overseas Highway, where congestion often quickly spoils holiday inertia. Key West Express instead turns the sea into a shimmering freeway to relaxation, often getting the vacation kick-started before feet hit solid ground.

With a fleet of jet-propelled catamarans, travelers savor smooth sailing along their treks. Riders can nest inside air-conditioned interiors, where bartenders stir up libations and flat-screens make time fly by, or they can gorge on sunshine and views from the outdoor decks. Upon arrival, travelers can use the second half of their round trip to return home at a later date, after they've guzzled their fill of Cuban sandwiches or written a sequel to The Sun Also Rises.

1200 Main Street
Fort Myers Beach,
FL
US

With more than 31,000 nautical miles of sailing under his boat shoes, Captain David Richardson is more than capable of navigating his sailboat, Sundance, on the leisure cruises for which he has become known. The half-day charters he leads out of Bonita Bill's Waterfront Café take in the many moods of the Gulf of Mexico, from its tranquil disposition in the sun to the turbulent waters it experiences when it realizes it'll never be a full-grown ocean. The Sundance itself boasts comfy accommodations, from cushy seats to an on-board bathroom, and many passengers bring their own food on board to eat while ogling jumping dolphins.

702 Fishermans Wharf
Fort Myers Beach,
FL
US