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Combine heart-pounding parasailing with a peaceful sunset sail in Key West for the ultimate ocean adventure. From thrilling water activities to delicious food and drinks, discover why this day trip is a favorite for visitors.
Combine heart-pounding parasailing with a peaceful sunset sail in Key West for the ultimate ocean adventure. From thrilling water activities to delicious food and drinks, discover why this day trip is a favorite for visitors.
Book with Sunset Watersports
Verified experiences and guided adventures in the surrounding area.
Operated by Sunset Watersports · Key West, Florida
Experience the perfect blend of thrill and relaxation with Sunset Watersports' "Do It All With Parasailing & Sunset Sip & Sail" adventure in Key West, Florida. This private outdoor experience packs an unforgettable day filled with adrenaline and calm seas. Start with an exhilarating parasail ride, offering breathtaking aerial views of the turquoise waters and vibrant coral reefs that surround Key West. After landing, hop on for the Sunset Sip & Sail, a serene sailing trip where you can unwind with a refreshing drink as the sun dips below the horizon, painting the sky with stunning hues. Beyond these highlights, this adventure embraces a variety of water activities including jetskiing, snorkeling, rafting, climbing, banana boat rides, and more, providing non-stop excitement for adventure seekers of all ages. A delicious grilled lunch and unlimited draft beer are served aboard, making it the perfect way to refuel while enjoying ocean breezes. Whether you’re celebrating a special occasion or simply want to soak up the island vibes, this unique combo delivers unmatched value and memories that last a lifetime. Situated in the vibrant Key West harbor, the experience is accessible and ideal for travelers staying nearby. The expert guides ensure safety and fun, making this private boat and water activities package a must-do for Florida’s southernmost gem.
moderate.
5–7 hours.
Participants should have a moderate fitness level to enjoy parasailing, climbing, and watercraft activities comfortably.
No prior experience is needed; the guides provide full instructions and ensure your safety throughout.
Yes, a delicious grilled lunch and unlimited draft beer are included, served onboard during the sail.
Bring reef-safe sunscreen, swimwear, a towel, and a waterproof camera or case for the best experience.
Children aged 6 and above can participate with parental supervision; however, some activities may have height or weight restrictions.
The combined parasailing and Sunset Sip & Sail adventure typically lasts between 5 to 7 hours.
Cancellations made 48 hours in advance are fully refundable; weather-related changes are communicated promptly with rebooking options.
Key West has a rich maritime history as a former shipwreck capital, which shaped its diverse cultural heritage and lively waterfront.
Sunset Watersports supports coral reef protection initiatives, encouraging guests to use reef-safe products and respect marine habitats.
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.
Book with Sunset Watersports