Key West: Parasailing Over Historic Seaport & Longest Flight

Summary

Parasail high over Key West’s harbor with gentle lift-off and sea breeze

You’ll float above Key West’s historic seaport with gentle lift-off from licensed local crews, enjoying the island breeze and views that stretch past shrimp boats and yellow taxis. With one of the longest parasailing flight times in town (up to 15 minutes), plus an hour on the boat, you’ll feel both thrill and calm—plus maybe get your toes wet if you ask.

What’s the experience like?

I didn’t really expect to feel nervous, but my hands were sweating as we shuffled down the dock at Key West bight. The boats are lined up like a postcard — white hulls, pelicans bobbing nearby. Our captain, Mike, grinned and said, “You’ll forget your feet aren’t on the ground in about thirty seconds.” He was right. The harness felt snug but not tight; I kept fiddling with it until his mate, Tasha, gave me a thumbs-up and said I was good to go.

The lift-off is quieter than you’d think. Suddenly there’s just the wind in your ears and that distant hum of boat engines below. You can smell salt — not sharp, more like old rope and sunscreen. The whole Key West seaport spread out under us: little yellow taxis crawling by Mallory Square, water sparkling around the shrimp boats. I tried to spot dolphins (no luck), but saw a stingray glide near the surface instead. Mike called up from below asking if we wanted our toes dipped — I laughed too hard to answer so Tasha just waved her arms in encouragement.

It’s funny what sticks with you after a day trip in Key West — like how quiet it gets when you’re up there parasailing, or how the sun feels different on your face when there’s nothing between you and the sky. We were up for maybe twelve minutes (they said it can be up to fifteen), but honestly time goes weird when you’re floating like that. Coming back down felt almost disappointing, except Tasha handed me my camera and I realized my grin looked ridiculous in every photo. Still worth it.

Step-by-step itinerary

Day 1 — Parasailing over Key West Seaport

• Meet friendly staff at Key West Bight
• Board state of the art parasail boat
• Get geared up by licensed crew
• Parasail high above Key West island
• Enjoy 8-15 minute flight views
• Optionally dip toes in water
• Capture photos with crew or own camera

Top questions

How long is the parasailing flight over Key West?

The flight averages 8-15 minutes per person.

Is pickup included for this Key West parasailing tour?

No, hotel pickup is not mentioned as included.

Can I bring my own camera or GoPro?

Yes, you can bring your own GoPro or camera on board.

Are there photo packages available?

Yes, ask the crew about their photo package options during your trip.

Is this activity suitable for people with health conditions?

No, it’s not recommended for travelers with spinal injuries, pregnancy, or poor cardiovascular health.

How long do you spend on the boat during this tour?

You’ll spend up to an hour on the boat including preparation and flight time.

Who operates this parasailing tour in Key West?

The tour is run by Sunset Watersports, a local company with over 36 years of experience.

Will my feet touch the water during parasailing?

If you want your toes dipped in the water, just ask the captain or crew during your flight.

What’s included

Your experience includes a full parasail ride above Key West’s historic seaport from state-of-the-art boats with all safety gear provided; friendly licensed crew will get you set up and offer optional photo packages—plus they’ll even dip your toes in if you ask before gently bringing you back down after your flight.