Sailing in The Villages

Select Local Merchants

Each time Captain DJ McCabe leads a sailing lesson, a smile of familiarity crosses her face at the sight of students' widening eyes as the sails catch wind and glide the boat across Lake Monroe. In the silence of the 9,406-acre freshwater lake, sailors can catch glimpses of rare wildlife as the vessel drifts past bathing manatees, soaring herons, and bald eagles snatching each other's toupees. A range of lessons taught by United States Coast Guard captain acquaint aspiring sailors with the trusty rigs, and more advanced students can sign up for certification courses, which follow ASA teaching curriculums to instill safe and steadfast sailing skills. Stationed adjacent to Monroe Harbour Marina, U-SAIL keeps a fleet of 8 boats ranging from 18 feet to 30 feet long and lavishes sailors on land with amenities such as abundant parking, wireless Internet, showers, and laundry machines. U-SAIL is located in the historic downtown district, which boasts myriad restaurants, art galleries, and unique shops.

531 N Palmetto Ave
Sanford,
FL
US

Cypress trees sway in the breeze, lush tropical vegetation soaks up the sunshine, and white sandy beaches glisten nearby as Buena Vista Watersports' rental jet skis, paddleboards, kayaks, canoes, and pontoons tote adventurers across the spring-fed waters of Lake Bryan alongside waterskiers and wakeboarders. The Key West–style resort, located just east of Disney World, allows families and friends to glimpse local wildlife as they skim scenic shorelines and chase picturesque settings at an aquatic reservoir as vast and secluded as Bigfoot's bathtub. The resort's alighted tiki torches and palm trees that border its tiki bar and pavilion attract groups for company picnics or private events such as weddings and parties, during which revelers can partake in watersports, dance to reggae, or watch a fire-dancing show.

13245 Lake Bryan Dr
Orlando,
FL
US

After spending their youths on the sea sailing, water skiing, and fishing, Cynthia and Jay realized they were in very real danger of spending their adult lives behind the desks of corporate jobs. So, when they got the chance to re-immerse themselves in the aquatic world by buying an inland marina at Lake Fairview, they jumped at it.

Today, they and their team of certified instructors lead sailing experiences on that glassy blue expanse and rent a wide assortment of seafaring vessels. They pile visitors in pontoon boats, two-person pedal boats, kayaks, and sail boats to navigate the lake for on-water picnics and fishing expeditions. Should renters get hooked on the experience, the staff can happily help them purchase new and used sailboats, fishing boats, runabouts, and ski boats. For land-based celebrations, their tiki hut-style gazebo, complete with a panoramic view of the lakeshore, accommodates guests during company retreats, birthdays, and lake monster sting operations.

4503 N Orange Blossom Trl
Orlando,
FL
US

As the St. Johns River winds through the Everglades of central Florida, it flows past forests of old-growth cypress trees. Bald eagles perch on branches draped in spanish moss, and below, blue herons and alligators prowl the edges of floating grass beds. Holding US Coast Guard Master Captain licenses, the guides of Airboat Rides at MIDWAY take passengers into this swampy wilderness aboard custom airboats. Launching from their own marina, the guides educate guests on the river's ecology and history via two-way headsets and stern, unwavering eye contact. These tours have earned multiple certificates of excellence from TripAdvisor, plus respectful nods from the river's turtles. In addition to airboat tours, the guides take guests out on seasonal gator hunts.

28501 East Colonial Drive
Christmas,
FL
US

In 1994, owners Chris and Margie Long established Boggy Creek Airboat Rides with a single, six-passenger vessel. Today, their fleet has grown to more than a dozen boats, and the business has whisked more than one million passengers through Orlando's nearby wetlands. From two locations, Boggy Creek's fan-propelled watercrafts launch into the Florida Everglades, exploring the swampy habitats of gators, turtles, eagles, exotic birds, and exiled Frankensteins. Four different tours offer varied experiences, including a night ride, during which participants observe red-eyed gators prowling for prey. US Coast Guard–certified captains helm every ride, which are safe for explorers of all ages—even infants.

3702 Big Bass Rd.
Kissimmee,
FL
US

At Daytona Beach Parasail, flightless humans can highlight day trips to Daytona Beach with a parasail adventure. After taking off from the flight deck of a boat piloted by a USCG-licensed captain, customers soar 2,000 feet in the air, which is the perfect height for catching scenic glimpses of the world-famous shoreline. No previous knowledge of parasailing is required. The entire excursion takes about 45 minutes, which includes the boat trip out and back. Single flights last about 8 minutes; customers can team up with Groupon-bearing friends for a tandem flight, which will keep them floating for 14–16 minutes. Pack your camera if you want a friend to snap pictures of your airborne antics. Ferry customers receive free shuttle service to and from the boat.

4936 S Peninsula Dr
Ponce Inlet,
FL
US