Sailing in Iona

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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

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

Gulf Coast Kayak sits on the edge of Matlacha Pass Aquatic Preserve, a scenic sprawl of estuaries, back bays, and mangrove tunnels roofed by the interlaced branches of waterside trees. Their single and tandem kayaks give paddlers a way to drink up this scenery, instead of waiting on the shore, thumbs-outstretched, hoping to catch a ride from a passing mermaid. Alternatively, paddlers can opt for a guided tour, such as the Sunset Birding Tour, which can afford birdwatchers glimpses of osprey, herons, and spoonbills. For those who cannot make it to their storefront, Gulf Coast Kayak is able to deliver kayaks anywhere in Matlacha or Pine Island for a fee.

4530 Pine Island Rd NW
Matlacha,
FL
US

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

The adrenaline junkies at Estero Island Parasail send guests soaring through clear Floridian skies whether it's warm or cold. Their small fleet of powerboats cuts through Gulf waves as parachutes carry guests high into the sky and back down to the water's surface to avoid collisions with low-flying UFOs or for quick dips into the sea.

5550 Estero Blvd
Fort Myers Beach,
FL
US

FishSkinner Charters fishes inshore in sanibel and Fort Myer Florida. We target species such as Redfish, Tarpon Trout and Snook. We also offer shelling and dolphin tours to Cayo Costa Island.

15351 Briarcrest Cir
Fort Myers,
FL
US