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Key West Parasailing
Over 2,000 5 Star Reviews

Key West Parasailing

"Key West's #1 Rated Parasailing"

Pricing: Save $10 Use Code PARASAIL10

– Parasail Flight: $79 Now $69.95

– Parasail Special (9am): Only $60

Trip Highlights:

– Breath Taking Views Of Key West

– Longest Flight Times

– Voted Top Key West Experience

Quick Highlights

Departure Time: Hourly From 9am – 6pm
Includes: State Of The Art Equipment, Highest & Longest Flight Times

Trip Details

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

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.

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.

This trip is powered by Conch Republic Parasail LLC

Key West Parasail Photos

Online Special Save $10

Pricing: Use Code PARASAIL10

  • Parasail Flight: $79.95  $69.95
  • Parasail (Early Bird): $79.95 $60

Why Book With Us?

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

BOOK TRIP

Key West Parasailing Video

Some Recent Reviews

  • Parasailing: I would highly recommend My three children (13,13,10) went parasailing in the morning. The check in was super easy. Loved the offer for pictures and video from the crew, it was worth the money and better shots than I would have done. The kids... read more

    Sandy P. Avatar
    Sandy P.

    Parasailing Was Awesome! Matt and Eion did a wonderful job of providing a memorable experience
    Sunset Watersports Trip Review: Key West Parasailing

    Robbie Stabler Avatar
    Robbie Stabler

    Parasailing Was Awesome! The parasailing crew was awesome and made everyone feel comfortable on our trip to Key West. The first mate did a great job of getting my 8 year relaxed and past her fears of going. I can’t thank him enough... read more

    Paul M. Avatar
    Paul M.
  • Best Thing To Do In Key West Best experience was the parasailing... amazing to see Justin get us ready to parasail & take amazing photos!!
    Sunset Watersports Trip: Parasailing

    Michael B Avatar
    Michael B

    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... read more

    natalieh941 Avatar
    natalieh941

    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... read more

    katkwiatkowski Avatar
    katkwiatkowski
  • 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... read more

    M Laylin Avatar
    M Laylin

    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...
    read more

    ImaPrettyDecentGuy Avatar
    ImaPrettyDecentGuy

    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
  • 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... read more

    rjonesiv Avatar
    rjonesiv

Frequently Asked Questions

How long is the ride?

You will be on the boat for up to an hour as each group is sent up for their parasail flight. On average guests get for up to 8-15 minutes. We are proud to offer the longest flight times in Key West.

COVID Policies

COVID Policy Overview

  • All equipment will be cleaned and sanitized prior to use.
  • Trips will operate at a reduced capacity.
  • All food and drinks will be served by our team members, who will be taking extra precautions to ensure safe prep as well as serving.
  • Hand sanitizer will be readily available throughout our facilities and on each boat.

Sunset Watersports is proud to have been an industry leader for Key West watersports for over 35 years and we look forward to working together with our community leaders to overcome these challenging times. Now more than ever, we are grateful for our guests, team members & our Key West community. We encourage you to book your trips in advance and give you the assurance that you can cancel up to 24 hours to depart time for a full refund.

Map & Directions

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.

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 tandem or triple parasail flights.

Is there parking?

There is a city operated parking lot on Caroline St for $4 an hour, as well as
metered street parking and a nearby garage on James and Grinnel Street.

What is the cancelation policy for weather?

Our captains analyze the weather on the day of the scheduled activity. If they determine that the trip will be unsafe, the trip will be postponed or canceled. Our office will reach out immediately to try to reschedule our guests’ activity if possible, but we will issue full refunds if need when we cancel the trip.

Is Sunset Watersports open on Holidays?

Yes, we operate every day, 365 days a year in Key West.

Where is the check-in location?

Guests check into our office along the Historic Seaport Pier at 201 William St,
right next door to the Waterfront Brewing company and the Marker Hotel. We
also depart from Smathers Beach at 2000 South Roosevelt BlVD, Key West FL 33040.

What do I need to bring with me parasailing?

Be sure to have a valid ID and the same card you used to purchase your tickets
upon check in. Other than that, dress comfortable as if you were going to the beach. Feel free to bring towels too.

How many people can fly together?

We can fly a maximum of 3 people if the combined weight does not exceed 500
pounds.

Additional trip information

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. On average guests get for up to 8-12 minutes.

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.

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