How to Propose While Parasailing – Don’t Lose the Ring!


You’re ready to pop the most important question of your life, asking your partner to marry you. You’ve always envisioned a big, amazing proposal, and you think parasailing is just the opportunity you’ve been looking for. How do you propose from a parasail?

Here’s how to propose while parasailing:

  • Book a side-by-side tandem parasailing adventure
  • Pay for videos and photos of your trip
  • Let the captain know your plans before you embark
  • Keep the ring in a secure, dry, accessible place
  • Adjust yourself to the feeling of parasailing
  • With a steady hand, pull out the ring and propose
  • Put the ring on your partner’s finger and don’t drop it!

In this article, we’ll elaborate on the above 7 steps so you can rock your wedding proposal and create the kind of unforgettable and romantic memory that will always make your partner smile. You’re definitely not going to want to miss it! 

Want to Pop the Question on a Parasail? Follow These 7 Steps! 

Book a Side-by-Side Tandem Parasailing Adventure

Before you can propose while parasailing, you need the actual parasailing trip in the books. Depending on where you live, you may schedule a ride in your neck of the woods or thereabouts. You could even go all-out and plan a romantic tropical vacation for the proposal.  

Our advice is to always reserve your parasailing slot early, even way early. Atlantic Parasail in Wildwood, New Jersey says that, in the summertime, they can be booked at least two days ahead of time since everyone wants to parasail during the warm season. Even in parts of the country like Florida where it’s hotter for most of the year rather than just the summertime, tourists can fill up those parasailing slots fast. 

When you’re scheduling your parasailing adventure, reserve tandem seats, which are seats for two. As we discussed in our post about tandem parasailing, you can sit either back-to-back or side-by-side with your partner. You do not want to be front-to-back if you’re planning a romantic proposal. You won’t be able to see your partner or give them the ring!

Double-check before you secure your parasailing reservation that the two of you will sit beside one another.  

Pay for Videos and Photos of Your Trip

A day of parasailing on average costs $45 to $200. Since you’re a twosome, your trip will already be a little costlier. Even still, be willing to pay extra for photos and videos of your parasailing adventure. The parasailing company can capture that precise moment you unveil the ring and surprise your soon-to-be fiancée! That’s a memory you’ll want to hold onto forever. 

We know what you’re thinking. Can’t you just bring your phone with you and snap some pictures? Yes, but think of how close you’ll be sitting with your partner. You two can’t spread your arms apart all the way without hitting each other when tandem parasailing. Actually, you can’t spread your arms half the way out. It’s close quarters. You won’t get the kinds of photos you want.

Let’s say you strapped a GoPro to your head, which some parasailers do. In a situation like a marriage proposal, you’re only getting your fiancée’s point of view, not yours. You’re a part of the couple too, so you deserve to be seen. 

That’s not to say you shouldn’t film on a GoPro if you want to, but splurge for the pro footage from the parasailing company. Once you see it, you’ll be glad you did. 

Let the Captain Know Your Plans Before You Embark

This is one of the most important parts of the process, so please, please don’t forget it. Parasail captains are used to dealing with proposals, but they can’t know you want to propose to your partner if you don’t say anything about it. 

You can’t wait until you’re up in the air or about to embark on your parasailing adventure either. By then, it’s too late. You can really only communicate with hand signals at that point.

What we suggest you do is this. On the day of your parasailing trip, get there a little early. Ask to talk to the captain or someone who can put you in touch with them, but don’t be obvious about it. When you connect with the captain, explain to them that you’d like to propose. The captain should be more than willing to accommodate you.

Some parasail captains might extend your ride a little longer so you have more time to overcome your nerves and ask the question. The captain and their crew will also be the first to congratulate you two once you land on solid ground. 

Keep the Ring in a Secure, Dry, Accessible Place

You put a lot of time and care into selecting the right ring for your partner, and it was anything but cheap. Protect the ring like the big investment it is by putting it somewhere safe until you need it. 

What you wear when parasailing is up to you. Some parasailers choose swimwear because they want to spend the rest of the day at the beach after they’re back on dry land. Other parasailers wear clothes since you don’t really get wet when parasailing unless you want to. 

Whether you decide on everyday wear or swimwear, you need a pocket that’s large enough for the ring box. It’s best if the pocket zips closed so you don’t have to worry about the box slipping from an open pocket. 

Is it a little inconvenient to have to unzip your pocket to pull the ring out when the big moment comes? Yes, but it’s the best route to take to safeguard your ring! 

Adjust Yourself to the Feeling of Parasailing

You probably aren’t a first-time parasailer if you had the idea to propose while up in the air. That said, depending on which company you fly through as well as the weather conditions that day, every time you parasail is a little different. This time is actually very different since you have fluttering butterflies in your stomach.

You’re going to be nervous about proposing, but take the time during the parasailing ascent to try and calm yourself down a little. Practice deep breathing or just watch the peaceful ocean waves for a few minutes. Remember that you don’t have to propose the first two minutes you’re in the sky. Most parasail rides last at least an hour, so give yourself a bit of time to prepare. 

In the meantime, try to play it as cool as possible. You don’t want to tip off your partner that you’re about to propose because you’re acting extra nervous or excitable. This is sometimes easier said than done though, we know!  

With a Steady Hand, Pull Out the Ring and Propose

Okay, here it comes, the moment you’ve been dreaming of. It’s time to propose. The ring will be in a zippered pocket, maybe the one opposite the side nearest your partner.  That will allow you to subtly yet smoothly unzip the pocket and retrieve the ring box. 

We have to say this: you cannot have shaky hands or butterfingers here. You’re 500 feet up and all that’s below you is the ocean, which will hungrily swallow up the ring if it slips from your fingers. If your hands are shaking, then take a few deep breaths until you feel a little more relaxed.

You can’t get down on one knee when proposing on a parasail–obviously–but not all women care about that sort of thing anyway. 

With the ring in hand, turn to your partner and say whatever feels most natural for you two as a couple. Perhaps that’s a long, romantic speech or maybe you just ask the question outright. It’s your proposal, so do what you want! 

Put the Ring on Your Partner’s Finger and Don’t Drop It!

Your partner has said yes and you two are going to get married! Now it’s time to slip the ring on their finger. You feel so much better having gotten the proposal out of the way, but don’t let your nervous energy cause you to lose the ring now. Pull your fiancée’s hand close to yours and slip the ring on their finger. That way, there’s less opportunity to drop it.

Then sit back and enjoy the rest of the parasail ride as an engaged couple. When you land, you’ll have lots of friends and family to call or visit with so you can share your good news. This is only the beginning of what will be a very exciting time! 

Final Thoughts

Proposing to your partner on a parasail is super romantic and a little more intimate than doing it at a filled sports stadium or a packed restaurant. It’s just the two of you up in the air and thousands of miles of ocean below you. What can be better than that?

Now that you know how to propose while parasailing, we just want to stress the importance of keeping the ring secure in your pocket and not dropping it. That’s the biggest risk when parasailing hundreds of feet up over the ocean, but in this case, we’d say the risk is much smaller than the reward! 

Geoff Southworth

I am a California native and I enjoy all the outdoors has to offer. My latest adventures have been taking the family camping, hiking and surfing.

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