Tours in Cypress Lake

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The husband-and-wife team behind Adventure Lifestyle lead intimate tours of South Africa, Egypt, Europe, New England, and sailing excursions around Florida. Small groups can ride a camel around the pyramids of Giza or take a boat cruise down the Seine. Guides Rudi and Jenny speak a variety of languages and have lived in numerous countries, granting them the expertise to give memorable tours.

568 9th Street South
Naples,
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

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 Blvd
Fort Myers Beach,
FL
US

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.

645 Old San Carlos Blvd
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

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