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
1. Historic Seaport 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 Deal
Book 9am Special $45
Book Smathers Beach $50
Book Historic Seaport $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
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Parasailing! 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
ImaPrettyDecentGuy1/16/2020I 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. Powell1/02/2020High-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 
rjonesiv11/25/2019
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
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$49 Sunset Sip & Sail
Includes:
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- 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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