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Key West Parasail

Departs: Hourly from 9-6pm

9am Special $45
Single Flight $50

Highlights: State Of The Art Equipment & Parasail Boats, Highest & Longest Flight Times

Location: 201 Williams St Key West FL

Book Direct Lowest Price Guarantee

Departure Time: Hourly from 9am to 6pm

Includes: State Of The Art Equipment & Parasail Boats, Highest & Longest Flight Times

Key West Parasailing with Sunset Watersports in Key West, Florida
Sunset Watersports is the oldest parasailing company in Key West, Florida.  If you are looking for a great parasail ride let us take you up over the famous Key West bight. We use state of the art boats and use the best equipment available. All of Sunset Watersports fleet of parasail boats are all coast guard inspected and certified. Nothing but the newest & the best equipment for our flyers.

Now With 2 Locations

1. Historic Seaport – Fly high above the island and get a one of a kind view of the Historic Seaport. Float high above the sea as you get to see all of the other charter boats, cruise ships, resorts & much more.

2. Smathers Beach – Fly high above Smathers Beach and get a unique view of the south side of the island. You will float high in the air as you get to see the crystal clear beach waters, shallow water reef, marine life, kayakers & much more.

Our crew offer a professional picture package that can be loaded directly to your phone on the boat. Let Sunset Watersports show you a great time with a Key West Parasail ride.

Book direct with us and enjoy our Lowest Price Guarantee.

Key West Parasailing

201 Williams St Key West FL 33040 (Google Map)
Please check in 30 minutes prior to departure.

1. Historic Seaport Location

2. Smathers Beach Location

Key West Parasailing With Sunset Watersports in Key West, Florida

Join Sunset Watersports, Key West’s Original Watersports Company and Florida’s 1st Parasailing Company for the best parasailing trip in Key West.

We have been parasailing in Key West for over 35 years. With more parasail trips than any other company we are proud to offer the safest and most experienced trips.

Sunset Watersports is the only Key West parasail company with multiple locations and state of the art boats. Step easily from the dock onto our boat as you are greeted by our crew and captain. Enjoy tropical music as we cruise on out to the crystal clear Key West waters. Our crew will seat you safely in the parasail harness and slowly raise you in the air, flying you high above Key West, gaining a birds eye view.

Key West Parasailing With Sunset Watersports in Key West, Florida

Join Sunset Watersports, Key West’s Original Watersports Company and Florida’s 1st Parasailing Company for the best parasailing trip in Key West.

We have been parasailing in Key West for over 35 years. With more parasail trips than any other company we are proud to offer the safest and most experienced trips.

Sunset Watersports is the only Key West parasail company with multiple locations and state of the art boats. Step easily from the dock onto our boat as you are greeted by our crew and captain. Enjoy tropical music as we cruise on out to the crystal clear Key West waters. Our crew will seat you safetly in the parasail harness and slowly raise you in the air, flying you high above Key West, gaining a birds eye view.

Best Value

Book 9am Special $45

Book Now $50

Why Book With Us?

  • LOWEST Prices Guaranteed
  • Over 35 Years In Key West
  • Award Winning Watersport Company

Book Online or Call 855-378-6386

Key West Parasail Photos

Key West Parasailing Video

Some Recent Reviews

  • 5 star ratingPARASAILING - BOOK THIS COMPANY From check-in to returning to the dock with my crew was EXCELLENT!! The lady who checked us in was friendly, the two guys that took me and my 3 young adult girls were awesome. They were funny, friendly, explained safety and just made our time on the boat and in the air super fun! The music was nice too.

    ALSO we...
    read more

    natalieh941 Avatar
    natalieh941
    3/12/2020

    5 star ratingAmazing Adventure!! Parasailing with Sunset Watersports was a great experience. I was surprised at how easy they made it for us and how enjoyable and relaxing the overall trip was. Our crew Miles and Tyler made it a very good experience for all of us. They took amazing pictures of us and gave us an incredible ride in the sky, along with... read more

    katkwiatkowski Avatar
    katkwiatkowski
    3/06/2020

    Parasailing with Sunset Watersports in Key West was amazing. They were awesome and made the trip worthwhile. 1st time parasailors and they made us feel confident with their expertise. The "dip" was the best part! This is the best thing to do in Key West.

    M Laylin Avatar
    M Laylin
    2/18/2020
  • 5 star ratingParasailing! First timer. I did the 9:00am $45 parasailing special. As far as I can tell, that's the cheapest price in Key West, by $10-$15. I called and booked at about 8:15 and they had availability.

    Easy walk from the cruise pier (maybe 1/2 mile or less). Easy check in. Great crew.

    Also, it turns out that you start and finish from...
    read more

    ImaPrettyDecentGuy Avatar
    ImaPrettyDecentGuy
    1/16/2020

    I worked for years as a tour guide and this place is state of the art. Friendly guides that have tons of knowledge on the local eco system, the best in the keys. If you’re going parasailing, etc. GO HERE!

    J. Powell Avatar
    J. Powell
    1/02/2020

    5 star ratingHigh-Flying Fun We decided to go parasailing for a birthday treat. Taylor and Andrew were the perfect guides/hosts/calmer downers to help us up into the air. The boat and equipment was well maintained, clean and a totally fun place to be. We took off from the boat and landed on the boat. In between, we flew high over the beautiful waters of... read more

    rjonesiv Avatar
    rjonesiv
    11/25/2019

Frequently Asked Questions

How long is the ride?

You will be on the boat for about an hour as each group is sent up for their parasail flight. We are proud to offer the longest flight times in Key West. 

Can I bring a camera up with me?

Yes you can, however our parasail crew offers an amazing & professional photo package on the boat

Can I come to watch my friend?

Yes, you can come ride along on the parasail boat to watch your friend or family member, however there is a $20 per rider fee and is based on availability.

Is there a weight limit?

Yup, we can fly up to 3 passengers with a collective weight of under 500 lbs. Don’t worry we fly single, tandem or triple parasail flights.

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$40 Sunset Cruise

Includes:

  • 2hr Sunset Cruise
  • Unlimited Draft Beer
  • Live Music
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$49 Sunset Sip & Sail

Includes:

  • 2hr Sunset Sail
  • Open Well Bar with Mixed Drinks, Draft Beer & Wine
  • Live Music
  • Great Appetizers

$59 Dinner Cruise

Includes:

  • 2hr Sunset Dinner Cruise
  • Open Well Bar with Mixed Drinks, Draft Beer & Wine
  • Live Music
  • Tropical Food Buffet

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In Response To COVID-19

Our commitment to you: We are all in uncharted territory right now, we will continue to monitor the COVID-19 situation & implement procedures as directed. We already have made company adjustments to ensure our safety & cleanliness measures remain the strongest in our industry. With that said we have currently closed operations in accordance with city, county & state regulations until April 15th. Our office remains open to assist with any questions & future bookings. We look forward to speaking with you 305-296-2554.  

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