Soar above the crystal-clear waters of Key West with a thrilling parasailing experience at Smathers Beach. Enjoy breathtaking views and expert service on the area's longest and highest flights.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
1–2 hours
Fitness Level
Suitable for participants in average physical condition; minimal exertion required.
Wildlife
History
Key West’s waters have long been a hub for seafaring and trade, with parasailing emerging as a popular way to connect with the island’s maritime heritage.
Conservation
Sunset Watersports supports eco-friendly practices, emphasizing reef-safe products and sustainable boating to protect Key West’s fragile marine ecosystem.
Sunset Watersports
Soar above the crystal-clear waters of Key West with a thrilling parasailing experience at Smathers Beach. Enjoy breathtaking views and expert service on the area's longest and highest flights.
Sunset Watersports is a Key West watersports and boat rental company based at a full-service marina. The company operates the island's largest fleet of rental boats, offering pontoons, deck boats, and fishing crafts for full-day rentals and custom charters. Licensed captains are available for private half-day and full-day charters for up to six people, and experienced staff provide local guidance and safety briefings.
Sunset Watersports runs a diverse lineup of experiences: full day boat rentals, a Lily Pad Add On for an eight-hour floating mat adventure, a JetSki tour that covers 28 miles and visits landmarks like the Southernmost Point and Boca Chica Sandbar, and a Two Reef Snorkel Tour with Sunset Cruise — a three-hour snorkel aboard the catamaran The Miss Valyn with unlimited drinks after snorkeling. The Sunset Sip & Sail departs aboard The Sandie Cat featuring live music, appetizers, and unlimited drinks.
Land-based options include 4- and 6-person concierge golf cart rentals with safety features such as seat belts and LED headlights; the 6-person option includes gas. The Key West Kayak Tour combines mangrove paddling, wildlife viewing, a sandbar stop, lunch, and unlimited drinks.
All offerings emphasize safety, local knowledge, and memorable island experiences. Guests can customize trips to include snorkeling, fishing, dolphin watching, or leisurely cruising, making Sunset Watersports a practical choice for families, couples, and groups seeking trusted Key West adventures. Booking is available online and at the marina with flexible scheduling, clear pricing, and equipment maintained to industry safety standards by trained technicians daily.
Largest Fleet
Island's largest
Pontoons, deck boats, fishing crafts
Tours Offered
11 Experiences
Sea, land, and sunset adventures
Private Charters
Up to 6 Guests
Licensed captains available
Named Vessels
Miss Valyn & Sandie Cat
Dedicated boats for specific tours
Reserve boats, tours, or golf carts online or at the marina — licensed captains and flexible options available.
Wear Comfortable Swimwear
Choose swimwear that allows freedom of movement and quick drying, essential for parasailing comfort.
Apply Reef-Safe Sunscreen
Protect your skin and the delicate marine environment with eco-friendly sunscreen before your flight.
Secure Loose Items
Remove hats, glasses, and jewelry or secure them tightly to avoid losing them during flight.
Listen to Safety Briefings
Pay close attention to the crew’s instructions to ensure a safe and smooth parasailing adventure.
Reef-Safe Sunscreen
Protects your skin while preserving the local marine environment.
summer
Polarized Sunglasses
Helps reduce glare from the water for better visibility during your flight.
Lightweight Water Shoes
Provide comfort and protection when boarding or disembarking the boat.
Waterproof Phone Case
Keep your phone safe while capturing photos from the boat and in the air.