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    1. Local experiences/
    2. Key West, FL/
    3. Water Activities/
    4. Parasailing/
    5. Parasailing Over Smathers Beach

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
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    Parasailing Over Smathers Beach

    Soar up to 300 feet above Key West on a 10–12 minute parasail flight guided by a USCG-certified crew

    From$59

    Duration

    Up to 1 hour

    Ideal For

    Up to 12 people

    Includes

    Parasail flight, Safety gear

    Highlights

    Fly above Key West’s crystal-clear waters on a thrilling parasail ride from Smathers Beach. Spend up to an hour on the boat and enjoy 10–12 minutes soaring high for panoramic island views.

    1. Board a USCG-inspected boat with friendly captain
    2. Glide smoothly into the sky with gentle takeoff
    3. Soar up to 300 feet for sweeping island vistas
    4. Relax to tropical music during the cruise
    5. Feel secure with all harnesses and life jackets provided

    What's Included

    1. Tandem or triple flights available
    2. Up to 8–15 minutes of flight time
    3. Smooth takeoff and landing from boat
    4. Safety equipment and life jackets

    FAQs

    Q: Can I fly solo or with someone else?

    A: Solo, tandem, and triple flights are available, with final groupings decided on site based on weight distribution.

    Q: What is the maximum group size on the boat?

    A: The parasail boats can take up to 12 passengers.

    Q: Do I take off from the beach or the boat?

    A: All takeoffs and landings are done directly from the boat.

    Q: Is any safety gear provided?

    A: Yes. All needed safety equipment including harnesses and life jackets is provided.

    Q: Is there parking for parasailing?

    A: Yes. There is a city operated parking lot on Caroline Street for $4 an hour, along with metered street parking and a nearby garage on James and Grinnel Street.

    Cancellation policy

    Full refund with 24-hour notice. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows are charged the full price.

    Meeting location

    1901 S. Roosevelt, Key West FL 33040

    Experience provided by Sunset Watersports
    Experience provided by Sunset Watersports

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #K38EHC

    Parasail Flight

    $59.95

    Ages 5+

    0

    Private Charter

    $600

    Up to 12 passengers

    0

    Handpicked for you, so you can book with confidence

    • Best local prices

    • Flexible cancellation

    • Private and secure

    Each booking directly supports small businesses in our community.

    4.8 stars• 19.2K reviews

    Review summary

    4.8
    Excellent
    19.2K reviews•Google Maps

    Sunset Watersports offers a solid range of activities from parasailing and jet skiing to snorkeling trips and dinner cruises, with most visitors leaving genuinely impressed. The parasailing consistently gets rave reviews, with guests like Wyatt and various captains earning specific shoutouts for making the experience memorable and capturing great photos. The dinner cruises seem to be another winner, with Captain Kristen, Captain Logan, and others praised for their knowledge and service. People love the combination of sunset views, live music, cocktails, and the overall atmosphere. The snorkeling excursions also get strong marks, particularly when captains like Kristen find calm spots on the reef and crews like Kevin, Maggie, Helen, and McKenzie take time to explain everything thoroughly. That said, there are some hiccups worth noting. One detailed review painted a concerning picture of the water adventure park experience, citing inattentive staff more focused on their phones than guest safety, mediocre food (boiled hot dogs and chicken nuggets), and a snorkeling setup that felt underwhelming. Another guest had a truly disappointing sunset sail where the crew couldn't even get the sail up, leading to an hour spent circling near the dock with static-filled music and subpar food and drinks. While these negative experiences seem to be outliers given the overwhelmingly positive feedback, they suggest consistency can vary depending on which activity you book and which crew you get. The jet skiing and parasailing appear to be the safest bets if you're trying to decide what to book.

    What people are saying

    Review 1 of 5
    5/5

    Fabulous evening on the Sandie Cat with friends! Captain and crew were attentive and very friendly. It looked like there was rain all around us, but our wonderful captain steered us between the storms. The boat was not overcrowded at all, and there were plenty of places to stand or sit to enjoy the view. Live music was provided and a wonderful, complete dinner buffet was included too. A nice touch as we boarded the boat – rum punch was premade and ready to grab while we listened to the captains instructions on safety.Would 100% recommend and hope to go again next time we are in Key West.

    Photo of Sally Bartlett

    Sally Bartlett

    October 10, 2025

    Review 1 of 1
    5/5

    Fabulous evening on the Sandie Cat with friends! Captain and crew were attentive and very friendly. It looked like there was rain all around us, but our wonderful captain steered us between the storms. The boat was not overcrowded at all, and there were plenty of places to stand or sit to enjoy the view. Live music was provided and a wonderful, complete dinner buffet was included too. A nice touch as we boarded the boat – rum punch was premade and ready to grab while we listened to the captains instructions on safety.Would 100% recommend and hope to go again next time we are in Key West.

    Photo of Sally Bartlett

    Sally Bartlett

    October 10, 2025

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