• Jessie Ladipo

Cheat Sheet for Popping the Question in Paradise

Updated: Aug 17



Whether you were college sweethearts, met on a blind date, or found love online, it's time to commit to forever. But figuring out how and when to pop the question is a significant undertaking. What kind of ring should you get? Should you go big and invite all your friends and family? Maybe an intimate proposal for the two of you is the best idea? You want it to be romantic and memorable. One of the best ways to make the moment special is to drop to a bent knee during a romantic getaway. Surprising, your sweetie on vacation is sure to be a hit! So here is my cheat sheet for popping the question in paradise.


Pick a Destination That You Both Love


Are you thinking of planning a destination proposal? It would be best if you considered what do you two like to do as a couple. Shopping? Skiing? Paddleboarding? Surfing? Did you profess your love for the first time on the beach in Amalfi Coast? Pick a place that has meaning to you both as a couple and use it as a starting point to plan your proposal. It doesn't have to be a world-renown romantic city, like Venice, and the trip doesn't have to be over the top. The most important thing is that you're both thrilled to be there.


Jessie's Practical Tip:

Getting engaged is a whirlwind! It is especially true if you jet off to somewhere stunning and exotic. You will want to have a photographer capture every spectacular second so that you can revisit the moment over and over again. And you'll have the bonus of gorgeous photos for your save the date announcement!



Turn to the Pros

You know your sweetheart better than anyone else, but it can be tricky doing all the work yourself. Get some knowledgeable help. I have been planning proposals (both in town and in exotic locales) for seven years. Allow my team and me to take care of everything, from logistics to sourcing vendors. Your only job will be to ask the question; I will take care of perfecting your vision. With hundreds of proposals under my belt, I know a thing or two about making yours memorable and worry-free. I can help you stay calm and collected and enjoy the day because it's a massive milestone for you too. I will take care of all the minutia, and you get all the credit!



Do Your Research Before You Plan


Even if you're usually fly by the seat of your pants, a destination proposal will require planning. First, does your destination have any cultural traditions or no-nos that you need to know? In many countries, proposing inside a sacred temple would be considered bad practice. Are you thinking about asking at the of the Eiffel Tower at sunset? You'll need to know the hours of operation and the most scenic lookouts. Long lines and pushy tourists can ruin even the best-made plans.


Jessie's Practical Proposal Tip:

You can't control the weather or other tourists. If you pick a popular romantic spot, crowding can ruin the mood you are trying to create. But you can lower your stress level (at least a little) by writing down what you want to say. Plan your speech before you leave for your destination proposal.



Get Insurance on the Ring Before You Leave!

Life happens. The ring could slip off when you are snorkeling. You could lose it; you could get robbed. An insurance policy is not only financially responsible, but it guards the ring's sentiment, which is priceless.

Ask about insurance at the jeweler or check with your homeowners' insurance to add the ring-specific policy. Insurance is a small effort that brings massive peace of mind.



Protect the Ring Until You Propose

Are you waiting for the perfect moment to pop the question? Do you keep getting the jitters at the wrong moment? Make sure to lock the ring in a safe back at the hotel room. Don't take chances with one of the essential pieces of jewelry you will ever purchase. You'll feel better knowing the bling is safe while you're exploring with your sweetheart.


Jessie's Practical Tip:

Walking around Santorini with a diamond ring in your bag would be nerve-wracking! And it would also put you at risk of losing it. Plan to propose relatively early during the trip. I suggest dropping to one knee on the first or second full day of the getaway. Then you can pop the champagne, relax, and enjoy your time together.



Avoid Proposing During a Major Excursion

Proposing during an activity will afford you many moving parts that will complicate your proposal. The simpler you can keep things, the better. You would have to safely get the ring to your excursion site, which can be problematic if you have a bunch of strangers with you. Do you want to find out that the ring is too big when you are rappelling down a waterfall?


Jessie's Practical Tip:

Are you traveling with your engagement ring? Luggage can get lost, so put the ring in your carry-on. Checking valuables is always a bad idea. You can hide the bling by putting it in a fake box or your grooming kit. You don't want the TSA to ruin the surprise if they decide to go through your bags.


The secret element to a winning proposal while on holiday is the pre-planning. When I assist clients in planning their destination proposals, I take care of every detail before departure to line everything up. From spa reservations and finding a pristine stretch of beach for the special moment to making sure your room is brimming with your sweetheart's favorite flowers. Making popping the question is as stress-free as possible. I can't guarantee her answer, but I can help you plan every detail to ensure your trip is as romantic as possible. Maybe it's on a sunset boat trip in Positano or a sunrise hike up Mount Batur in Bali. I can turn your dreams into reality.


LET'S SWEEP HER (OR HIM) OFF THEIR FEET!



(859) 309-6229

info@tripstocherish.com

Monday–Friday 10am-6pm EST
Saturday 10am-2pm

Lexington, KY​

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