About this Experience
What you'll do:
Ready to live your best boat day? Grab your crew and cruise the crystal-clear waters of Destin with a 4-hour pontoon rental from Gilligan’s Watersports! You’ll captain your own boat (or hire a driver from our Skipper List for groups of 11 or less) and make your way to the famous Crab Island—Destin’s floating hangout hotspot. Swim, float, snack, and soak up the Florida sun with your favorite people. This is the ultimate DIY day on the water! Whether you're celebrating something big or just vibing with your crew, this is your time to anchor down and chill out.
Enjoy a 4-hour pontoon rental from Gilligan’s Watersports in Destin
Cruise from the Destin Harbor to the world-famous Crab Island sandbar
Swim, float, anchor, and relax in clear, waist-deep emerald water
Captain your own boat or hire an approved skipper (groups of 11 or fewer)
Build your own perfect boat day with music, snacks, drinks, and sunshine
Experience one of Destin’s most iconic and lively water destinations
Why this experience is perfect for your group:
Easy swim ladder access for quick dips at Crab Island
Bimini top for shade and comfort during hot Florida sun
Perfect setup for group photos and social media content
BYOB-friendly so you can bring your own food and drinks
Optional skipper available if you want a fully relaxed experience
About this experience partner:
Over a decade of experience in Destin watersports
Located directly on the Destin Harbor for fast, easy departure
Known for reliable pontoons and smooth rental operations
Ideal for birthdays, bachelor/bachelorette parties, and group outings
Focused on fun, safe, and memorable days on the water
Additional information:
Must be 18+ to rent
Boater’s license required for anyone born on/after Jan 1, 1988
Boat capacity: up to 12 passengers
Included: life jackets, map of the area, and full tank of fuel
What to bring: cooler, drinks/snacks, towels, sunscreen, floaties, speaker
Check-in: arrive 30 minutes early for paperwork and safety briefing
LocationDestin, FL
530 Harbor Blvd, Destin, FL 32541, USADestin, FL
Cancellation Policy
generous Cancellation Policy
Full refund on cancellations with 7+ days notice. No refund within 7 day window.
Reviews
Frequently Asked Questions
Do I need a boating license to drive the pontoon?
Yes—if you were born on or after January 1, 1988, Florida law requires you to have a valid boater’s license. You can take a quick online test before arrival or onsite at our location.
Can I hire a driver if I don’t want to captain the boat?
Yes! We have a Skipper List of experienced, approved drivers available for hire. Please note: groups must be 11 people or fewer when using a hired captain due to Coast Guard regulations.
Where can we go during the rental?
Most guests head to Crab Island, just a short cruise away from our dock. You’re also welcome to explore Destin Harbor and nearby areas, as long as you stay within our designated boating zone (we provide a map at check-in).
Can we split driving the boat during the rental?
Yes, multiple approved drivers can rotate as long as each meets Florida boating requirements and completes the safety briefing.
Is fuel included or do we pay extra after the trip?
Fuel is included with your rental, so you don’t need to worry about refueling or additional charges at the end of your trip.
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