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.
Under the capable direction of Captain Gene Becker, the 75-foot Fort Myers Princess glides into the Gulf of Mexico on a variety of day and night cruises. Certified by the U.S. Coast Guard to carry up to 135 passengers, the boat offers dual styles of relaxation on its decks: the climate-controlled lower level, where guests can sip on the ship's signature drink, the "Princess Punch," and the open-air upper deck that can accommodate more casual events. Sightseeing cruises put passengers up-close with southwest Florida wildlife and other water inhabitants.
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.
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.
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.