• For $25, you get a 90-minute sunset cruise for two (a $50 value). • For $30, you get a two-hour sightseeing cruise for two (a $60 value). Captain Mark’s Water Taxi glides along the glittering coasts of Cortez, Anna Maria Island, and Longboat Key, slipping past notable sights ranging from the arcs of leaping dolphins to the City Pier’s commerce-laden shores. Both tours shove off from Cortez Kitchen, where explorers can snag a bite before boarding the 26-foot Red Skyy, which ferries small groups of wayfarers through a backdrop etched with fishing boats, pelicans, and aquamarine waters. Ninety-minute sunset cruises slip past pods of feeding dolphins, staging ideal opportunities for photos and pitch-tuning vintage porpoise whistles. Cut a watery path toward Longboat Key during two-hour sightseeing tours, stopping intermittently for optional snacks at Mar Vista Dockside Restaurant and Pub, shopping excursions at Bradenton Beach City Pier, and searches for sand dollars with which to bribe crabby bartenders. All trips return explorers to the docks at Cortez Kitchen with their eyes full of seaworthy sights and their brains full of plans for flipper implants.
Island Scooter’s rentable cycles unveil the beauty of Anna Maria Island by facilitating daylong explorations of its sunny paths and shores. Helmets protect skulls, and island maps protect the pride of those who dislike asking for directions or accidentally biking through lobster picnic grounds. Starting at Silver Surf, the island’s picturesque landscapes unfurl before cyclists with each looping push of the pedal. Helpful staffers arrange drop off and pickup of people-powered mounts for couples wishing for a different starting point or those looking to take in the sunset from another island vantage, such as atop the parapets of a newly built sand castle.
Captain Anthony Leverett, the man behind Kingdom Business Charters, has fished the waters around Tampa Bay for more than 15 years. After casting countless lines, he mastered the finer points of catching snapper, grouper, kingfish, and cobia. Today, he passes this expertise onto others during fishing charters aboard his deep blue, 1988 classic Pro-Line fishing boat. The vessel features an illuminated cockpit and underwater LED lights, which allow Captain Leverett to fish at night or on days when the sun calls in sick.
The warm, sunny weather and postcard-ready sunsets of Florida's Gulf Coast draw vacationers to Anna Maria Island year-round, but visitors don't have to worry about sprawling high-rise hotels blocking their beachfront views—tall buildings are strictly forbidden. The historical Anna Maria city pier bustles with beach-themed stores and a popular ice-cream shop. The Anna Maria Island Historical Society displays regularly changing exhibits of period costumes and rare photographs in a museum located next to an old local jail open for tours or self-administered claustrophobia tests. The region's lush flora blooms at the Marie Selby Botanical Gardens, which encompasses 14 acres abounding with more than 20,000 exotic plants and trees. After a day of culture and horticulture, visitors kick back in eateries serving fresh seafood and fruity cocktails at tables set right out on the beach.
The thrum of the speedboat's engine carries through the water like an ice-cream truck's jingle. A 4-foot-high wake trails behind, fanning out into a fork as the speed increases and the passengers ready their cameras. Soon, a glistening fin breaks the surface. The first bottlenose dolphin seems to levitate on top of the wave while it bodysurfs for the sheer fun of it, then disappears back into the sea. Its pod follows suit, leaping, splashing, and riding the swells, soaking up the attention of the human spectators.
Sights like this are typical on the Dolphin Racer Speed Boat. The sunny yellow craft skirts across the Gulf of Mexico on 60- to 75-minute trips while up to 125 people lounge on the open deck and the captain narrates the sights of the passing beaches. Ample viewing space ensures that cameras can capture split-second jumps and spins when the dolphins heed the call to play. Whether it's because of the thrill of breaching, the pride in their celebrity status, or an underwater bet to see who can communicate with humans first, the dolphins' presence is virtually guaranteed—the boat offers a complimentary future cruise in the case of no-shows.
The crew at Kayak Valet has one mission: to get more people out and enjoying the local waterways and scenery via kayaks or paddleboards. Since storing, hauling, unloading, reloading, and potty training their own kayaks can deter people from boating, the team sets up shop to cancel out such deterrents. They take care of nearly every task, bringing all equipment necessary for a leisurely paddle on puddles of all sizes right to the launch site. The crew will pick up and deliver equipment to popular launch sites within Hillsborough, Pinellas, and Manatee Counties. To keep the aquatic adventure accessible, the shop rents only kayaks and standup paddleboards that can be piloted by anyone, experienced or not. Additionally, they give visitors tips on paddling and safety techniques and sell new kayaks, paddleboards, and accessories.