Key West's Original Watersport Company
Lowest Price Guaranteed 855-378-6386
Key West's Original Watersport Company
Lowest Price Guaranteed 855-378-6386

Parasailing Key West – Smathers Beach

(9 Reviews)
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  • LOWEST price in Key West
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We offer Key West’s Best Watersport trips & tours for the LOWEST price, guaranteed!


Availability : 12pm, 1pm, 2pm, 3pm, 4pm, 5pm
Smathers Beach Key West FL 33040
Parasail Trip Details

Key West Parasail – Smathers Beach

best parasailing in key west
Parasailing Trips All Day Everyday
Single, Double & Triple Rides








Parasail over Smathers Beach Key West for an unforgettable parasailing adventure. See Key West from 300 feet in the air as we fly the highest for the longest parasailing trips in Key West.

Sunset Watersports is the oldest parasailing company in Key West, Florida. If you are looking for the best parasailing experience, let us take you on a parasail ride you will never forget. Our parasail boats are state of the art and only use the newest and best equipment.

Our parasail crew even offers a photo package of fun and exciting professional photos and videos.

Departure & Return Location

Smathers Beach Key West FL 33040

Departure Time

10am, 11am, 12pm, 1pm, 2pm, 3pm, 4pm, 5pm

Check in 30 minutes prior to departure

Price Includes

  • Single, Double & Triple Rides Available
  • Key West's Longest Parasail Ride
  • Fly The Highest
  • State Of The Art Boats
  • State Of The Art Equipment
  • Friendly Crew
  • Photo Packages Available
Frequently Asked Questions

FAQHow 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 some of the longest parasail flight time here in Key West. Each flight is 8-12 minutes on average.

FAQCan I bring a camera up with me?

Yes you can, however our parasail crew offer a professional photo package on the boat.

FAQCan 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.

Parasailing Photos
9 Reviews
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Joan A

Family Traveller

These guys did a great job!! There were 10 people taken out at a time. You ride a “shuttle” boat out to the real boat that pulls you for the parasail. Life jackets are handed out and Hal helps everyone into the harnesses. They played nice music and had positive attitudes. Hal offered a picture package for everyone and took lots of pictures (80-100 per couple). You will get a little bit wet, anywhere from up to your knees to full body, but you can request to not touch the water and you won’t be brought low enough to touch. I was worried about my sunglasses falling off, so I didn’t wear them but it is much calmer in the air than expected so sunglasses and hats should be okay. You are out on the boat for about 1 hour roundtrip. It was a very safe and fun ride on the boat and during parasailing air time!! Highly recommend Sunset Watersports in Key West for parasailing and these guys as your instructors!

October 24, 2018


Group Traveller

Best parasailing experience ever!
No words to explain!! Go for it!! You will cherish this key west parasailing experience for a long time! I felt it was inexpensive too! They even took great pictures of our parasailing trip too.

October 19, 2018


Couple Traveller

Great Parasail Adventure and Free Parking
We really enjoyed our para-sail from Smathers Beach. Kevin professionally handled the boat. The parasailing was a wonderful experience that everyone should try at least once. With a small group (four of us), it was a quick ride out, switch boats, then the ride of a lifetime. The hardest time was coming back in after. We got the picture package, and they shot over 150 pictures with a short video as well. It was great for remembering the excitement of the ride. Free parking was great too!

October 19, 2018


Couple Traveller

Occasionally, my wife and I like to parasail whenever we’re in a coastal location. We decided to go parasailing with Sunset Watersports after talking with the very entertaining Patrick at their kiosk on Front St.

We had the first-in-the-morning parasailing trip and were joined by three other groups. Our crew (sorry, I can’t recall the names) were all very professional and kept operations running without fail.

Of all of the parasailing trips we’ve taken, this was by far the longest one we’ve been on (in terms of being aloft). This was more surprising considering that the other parties included 10 other individuals in total.

Sunset Watersports pricing was also better than their competitors in Key West. We definitely recommend them!

October 18, 2018


Family Traveller

Amazing Parasailing Trip
We go to Key West 2 or 3 times a year. My 10 year old son always wants to parasail and we always go with Sunset Waterspotrs. These guys are AMAZING! They are professional, fun, and make it an exciting and memorable adventure. Last Saturday we went sailing with Kevin and Red….what a fun way to begin our morning. If you want fun and adventure, go with Sunset. Professional, great equipment, clean, and reasonable. Making memories to last a lifetime!

October 15, 2018