About Gilligan's Watersports
Gilligan's Watersports is a locally owned operation that has grown into one of Destin's most recognisable watersport brands, running three convenient locations along Harbor Boulevard and Calhoun Avenue. Under new ownership and management, the company has invested heavily in fleet upgrades and staff training, earning a consistent 4.8-to-4.9-star average across thousands of Google reviews. Their harbourside positions mean guests can walk from restaurants and shops straight onto the dock and be on the water within minutes.
The Gilligan's lineup spans five core experiences. High-performance Yamaha WaveRunner rentals let visitors explore the Emerald Coast independently, while parasailing flights offer aerial views of the Gulf where dolphins, sea turtles, and stingrays are regularly spotted from above. Guided jet ski dolphin tours are led by crew members who know exactly where the resident pods congregate in Choctawhatchee Bay. Standard and double-decker pontoon boats — the latter equipped with waterslides — are the most popular pick for Crab Island day trips, and the Tipsy Tiki floating bar experience adds a party-boat twist that bachelor and bachelorette groups love.
Open daily from 8 a.m. to 8 p.m., Gilligan's offers some of the longest operating hours on the harbour, and same-day bookings are frequently available for guests making last-minute plans. Competitive online pricing and a well-maintained, relatively new fleet keep repeat visitors coming back season after season. For anyone looking for a one-stop watersport provider that can handle everything from a solo jet ski ride to a 14-person pontoon party, Gilligan's Watersports consistently delivers on the Destin Harbor.
