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List Of Key West Parasailing Trips

Multiple Parasailing Locations & Combo Deals In Key West

Featured Trip: Morning Parasail Special

The best parasail deal in Key West. The early bird gets this great parasail discount. There are limited spots available for this 9am special, so reserve your spots today! This is a parasail trip on the downtown seaport.

Was $59 Now Only $45

Time: 9am

Highlights: Brand New Equipment, Over 35 Years Parasailing In Key West, Photo Package Available On The Boat, Highest Flights, Longest Flight Times, Single, Double & Triple Flights

Location: 201 Williams St Key West FL 33040

Best Trips

Why Book With Us?

  • LOWEST Prices Guaranteed
  • Multiple Daily Trips
  • Best Snorkeling Locations
  • Over 35 Years In Key West
  • Award Winning Watersport Company

Book Online or Call 855-378-6386

Morning Parasail Pictures

Best Value: All Day Adventure with Parasailing

Key West’s most popular watersports combo package, The Do It All is action packed and includes a truly unique snorkeling experience around a sunken shallow water ship wreck. Join us on the Party Cat 65ft double decker catamaran for this 6 hour adventure. Enjoy parasailing, jetskis, kayaks, paddleboards, inflatable waterpark, trampoline & more. A total of 13 different watersport activities. This trip also includes a grilled lunch and draft beer when you are all done with the watersports.

Was $149 Now Only $139

Duration: 6 Hour Trip Departs At 10am

Highlights: Snorkeling, Jetskis, Parasailing, Inflatable Water Park, Kayaks, Paddleboard, Gilled Lunch 

Location: 201 Williams St Key West FL 33040

All Day Adventure Pictures

Beach Parasailing: Smathers Beach Parasailing

Join us on Smathers Beach for a unique parasailing adventure. We are the ONLY parasail company in Key West that parasails from the beach. Fly high above the island as you get one of a kind views of the beautiful beach side of the island.

Was $59 Now Only $50

Time: 10am-5pm Daily

Highlights: Highlights: Brand New Equipment, Over 35 Years Parasailing In Key West, Photo Package Available On The Boat, Highest Flights, Longest Flight Times, Single, Double & Triple Flights

Location: Smathers Beach Key West FL 33040

Beach Parasailing Pictures

Downtown Seaport Parasailing

Head to the historic seaport and parasail over the Key West harbor. Fly high above all of the boats and get unique views of Sunset Key. Don’t forget to ask about the photo package. This is one of Key West’s most popular trips.

Was $59 Now Only $50

Time: From 10am-5pm Daily

Highlights: Brand New Equipment, Over 35 Years Parasailing In Key West, Photo Package Available On The Boat, Highest Flights, Longest Flight Times, Single, Double & Triple Flights

Location: 201 Williams St Key West FL 33040

Downtown Seaport Parasailing Pictures

Parasail Combo: Tandem Parasail & Jetski Tour Combo

Save big when you book the parasail/jetski combo for 2. Get a tandem parasail flight at Smathers Beach and a 28 mile guided jetski tour around the island of Key West on our brand new jetskis. This is one of the most popular watersport combos. Save when you book them together. Includes a tandem parasail flight and one jetski for two guests. Book both trips on the same day or separate days. 

Was $258 Now Only $209

Jetski Times: 9:30, 11:30, 1:30 & 4:00 Daily

Parasail Times: 10:00-5:00 Daily

Highlights: Brand New Equipment, Over 35 Years Parasailing In Key West, Photo Package Available On The Boat, 28 Mile Guided Jetski Tour, Brand New Jetskis

Jetski Location: 2801 N. Roosevelt Key West FL 33040

Parasail Location: Smathers Beach Key West FL 33040

Parasail & Jetski Combo Pictures

Beach Pass with Unlimited Rentals & Parasail Flight

Looking for some more watersport activities. Try our Smathers Beach Pass. This pass is an all day beach pass with unlimited kayak, paddleboard, hobie cat rentals and includes a parasail trip for 1. Feel free to come and go as you please. This pass is good for all day. Parasail trip will be booked when checking into the beach hut for the pass. 

Was $89 Now Only $79

Time: Open All Day 9am-5pm

Highlights: Parasail Ride, All Day Equipment Rentals, Kayaks, Paddle boards, Hobie Cat Sailboats, Floats & More 

Location: Smathers Beach Key West FL 33040

Beach Pass Pictures

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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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