Bellair-Meadowbrook Terrace, FL Outdoor Activities

High-profile destinations often cite their high ratings on TripAdvisor, which named e2ride bike tours Jacksonville’s No. 1 attraction. However, few boast that they were highly rated by Harriet Beecher Stowe. Her iconic novel, Uncle Tom’s Cabin, is credited with helping to ignite the Civil War, but most of her opinions on travel have been lost to the ages—except on the company’s historical bike tour of Olde Mandarin. As the tour group winds past the lush area’s museums and public parks, the tour guide notes that Stowe dubbed the area “a tropical paradise.”

On the company’s other tours, guides offer equally juicy historical tidbits, such as that Riverside-Avondale was originally only occupied by just two homeowners or that Truman Capote vacationed in Springfield. As they learn about the past, groups cycle down present-day roads lined with homes in styles ranging from Tudor and Georgian to Star Warsian.

Situated near the flourishing wildlife of Big Pottsburg Creek, All Wet Sports stocks an arsenal of boards, boats, and apparel for careening across both land and sea. Kayaks, surfboards, and skateboards line the shop’s walls for purchase or rent, and more challenging activities such as windsurfing, kiteboarding, wakeboarding, and standup paddleboarding are made understandable for eager adventurers by a crew of deft instructors. On their chosen mode of transport, customers venture into the placid waters of Big Pottsburg Creek, teeming with such inhabitants as ospreys, manatees, and unemployed Disney characters.

After the tidal surge, 5 feet of water settled over the main office. Splintered fragments from 22 yachts floated by the docks and lay strewn across the highway. Investment advisor and maritime aficionado Don Shapray gazed toward the now-tame seas, surveying his crippled fleet. Though he and his business weathered 1983's Hurricane Alicia, he knew he couldn't stay in Houston. Memories of weather reports touting calm waters and seasonable heat called him to Jacksonville, where he rebuilt his sailing academy from the ground up. Nearly 30 years later, he's instructed more than 15,000 students in the art of sailing keelboats and sailboats. A team of certified captains helps him train students aboard a fleet of Sonar 23 and Precision 15 boats, each lightweight enough to allow for drag races against other boat gangs with names such as The US Coast Guard.

Southern Sailing's experienced captains sail year-round, but conduct their summertime lessons and cruises at night to avoid the brunt of the day's heat and seasonal storms. They teach sailors to navigate the St. Johns River's calmer waters, drifting up or downstream as the evening wind permits past trees, docks, and riverfront homes. Though they guide novice sailors through basic sailing overviews, instructors can also certify them through a 12-hour bareboat sailing program that begins with an educational DVD starring Don Shapray himself. In each on-water lesson, instructors coach students one-on-one, allowing for personal attention and hands-on instruction. When not teaching, captains ferry visitors through the waterways on chartered cruises, or help customers find their sea legs among a fleet of small yachts.

The wind picks up over the St. Johns River, catching the sails of Cap'n Don Stokes's fleet of boats and propelling the vessels along the coastline, where sailing instructors point out ospreys perched in the trees as the sea stretches into the distance.

This natural revelry is thanks to The Sailboat Club, whose crew frees members from the responsibilities of boat ownership—such as maintenance, insurance, and renting slips—and grants unlimited sailing on a fleet of sailboats. Additionally, as an accredited training facility of the American Sailing Association, the club encompasses a team of instructors who teach lessons for all levels of sailors, ranging from those who just noticed wind to experienced sailors seeking a captain's license.