Largo, FL Outdoor Activities

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 third annual St. Pete Oktoberfest, hosted by the Grand Central District Association, is St. Petersburg's largest beer festival, featuring craft-beer tastings and live music. Attendees can tipple samples from dozens of breweries, including Bell's Brewery, Dogfish Head, Sam Adams, Angry Orchard, and many others. A home brewer's challenge on Friday tests out homebrewed beers against old favorites, so home-beer enthusiasts can test out their recipes on actual people instead of the wild deer that show up in their backyards.

In addition to the extensive selection of microbrews and iconic beers, the two-day street festival also features live music, including performances from singer-songwriter John Kelly on Friday. Saturday's music merges rock, blues, jazz, and funk, with performances from Florida-native Damon Fowler, Bobby Lee Rodgers Trio, and Serotonic.

Sky Pirate Parasail's U.S. Coast Guard–licensed captains slip through John's Pass between Madeira Beach and Treasure Island while towing parasailers who glide under kaleidoscopic chutes tethered up to 1,200 feet in the air. After fastening their passengers, who range from school-aged kids to grandparents, into a secure harness, they fill the parachute's canopy with air and shuttle the skyward rider over the saltwater waves for an aerial jaunt. As the captain slackens the line and traces the coastline from offshore, the parasailer floats over the beach, the dolphins, and the gelatinous blob monster waving at sunbathers.

Looking out at the quiet, moonlit waters of the Gulf of Mexico, it’s impossible to know what’s on the line, other than that it’s big. Word has spread around the deep-sea-fishing boat, and now a crowd has gathered on either side of you. You pull the fishing pole back and guide whatever is snagged on the other end of the line nearer and nearer toward the halo of light illuminating the large boat. The splashes gradually become louder, and then a large lobster-red tail emerges from the water. A few fellow fishermen help pull the creature onto the boat, and proudly hold it up for the crowd—a 38-pound cubera snapper.

There are countless deep-sea-fishing tales like this one to be told at Hubbard’s Marina. During its many day or night fishing trips, its crew and guest fishermen board the US Coast Guard–certified vessels for excursions into the Gulf to reel in fish of all sizes, including large sharks and adult mermen. They also captain sunset cruises, dolphin-watching cruises, kayak tours, and even take to the streets during segway tours.

In 1962, Charles Redington commissioned a 1,200-foot-long fishing pier to be built in the Gulf, one of eight others like it in the area. Today, this long wooden walkway represents the last of its brethren, preserved and restored by the current owners, the Antonious family, who treasure its historic significance and excellent fishing. The waters surrounding the pier teem with sea life, such as flounder, eels, sharks, dolphins, and kingfish who burble "checkmate" when they get hooked. The crystalline Gulf waters provide a view of the vibrant reefs below, best seen and fished from the very end of the pier, which is reserved for those who purchase VIP passes. Since The Long Pier requires no fishing license, both amateur and professional fisherfolk can enjoy its sunny lengths and salty breezes by simply renting a rod and buying bait from the onsite tackle shop.

Boats dance and glide over the crisscrossing wakes carved into Tampa Bay, each craft anxiously revving toward its respective dock to arrive before closing time. All the while, a handful of boats remain on the open water, swaying atop the undulating waves as its passengers continue to enjoy the fiery sunset reflecting off the bay's surface. These select aquatic vehicles carry Lotto Boat's boat club members, who have access to a slew of exclusive perks, such as extended marina hours. Stationed at Harborage Marina, Lotto Boat's 10 rental vessels include kayaks, WaveRunners, and power boats equipped with GPS navigation systems. After hopping aboard a vessel, landlubbers can go jet-skiing, drift over to nearby tiki bars for dinner and live music, or take in scenic views of downtown St. Petersburg. Once patrons make their way back to one of Lotto Boat's two docks, they can take a dip in the marina's private pool while staffers thoroughly cleanse the boat of interior debris and exterior mermaid hitchhikers to prepare for the vessel's next excursion.