Everything you need to do before you propose in Maui

When working with Engaged on Maui to pull off your surprise Maui proposal, there are only a few decisions you need to make. We ask you to choose your proposal date, time of day (usually sunrise, morning, or sunset), package, and location. Then we take care of the planning and photography!

However, there are some tasks you can do on your own to prepare. Here are all the things you should do before you pop the question.

Make sure you and your love are on the same page

Before you think about asking, “Will you marry me?” you should be confident the answer will be, “YES!!!”

Marriage should be something you have discussed as a shared plan for your future together. Most importantly, you should make sure that the timing is right. If your sweetie has talked about life or career goals they want to accomplish before getting engaged, honor their goals and don’t jump the gun to get down on one knee just because you are coming to Maui.

Couple sitting in a flower circle on the beach after getting engaged

Save up and get the engagement ring

We can’t tell you how many times engagement rings have been delayed. Please don’t be one of those people who wait until the last minute to order an engagement ring. When you start saving up for a ring, research how long it will take for the ring to be ready before you start planning your proposal. Then take the estimated arrival date and add a few weeks. You should have extra time in between when the engagement ring will be ready and your proposal date. It’s better to have the ring in hiding than to risk it not arriving in time for your proposal.

You are responsible for getting the ring on time. We can’t refund you if the ring isn’t going to make it and you don’t want to propose without a ring.

Engagement ring balancing on lava rock with couple out of focus in the background

Talk to the people who matter

Asking for permission to marry, especially when phrased that way, can sound old fashioned. However, if your sweetie is close to their parents (or people who raised them), talking to those family members to get their blessing before you propose can be very meaningful. It’s a great way to show respect and grow your relationship with your future in-laws and is sure to gain you bonus points with your new fiancé.

If you tell loved ones when you are planning to propose, make sure they wait to hear from the two of you before they send texts of congratulations or champagne to your room. You don’t want them to spoil the surprise if they forget about the time difference or in rare cases where we have to reschedule due to weather.

If family members are going to be at the proposal, please let us know in advance as that may affect location options and what we do before or after the proposal.

Engaged couple smiles at the camera while their loved ones wait behind to surprise them

Set yourself up for success

This tip comes in extra handy if your sweetie is normally the planner in your relationship. If you know you want to propose in Maui, use going on vacation as an excuse to take the lead on planning and make your proposal part of your vacation itinerary.

You can say you were looking at fun things to do and want to pick a day (or a couple days) during your vacation where you get to choose what to do. Your partner can pick a different day to be in charge, and other days you can plan together. That way, you can plan your day strategically to make sure you are in the right place at the right time to pop the question.

Alternatively, you can start planning more dates and surprises before you go on vacation, so you taking the lead on planning something doesn’t seem so out of character and arise suspicion.

Man reveals surprise photographer there after proposal

It’s all in the details

If you aren’t able to pick a vacation day to plan, you still have to figure out how to get to the proposal spot at the right time.

Look at GPS to estimate how long it will take you to get there, so you know when you have to leave. Be aware that we don’t want you to arrive too early because you can’t beat the photographer there or show up before they are ready.

Come up with a cover story if you need to. Usually the best cover stories are simple, especially if you’re a bad liar. It can be something like, “I saw that this beach is known for turtles, and I wanted to check it out on the way to dinner.”

Pro tip: It’s okay to fib about your dinner time and restaurant if it puts you in a better position for your proposal location to seemingly be convenient and “on the way” to your dinner plans. Planning your proposal is the only time it’s okay to lie to your partner. When you’re celebrating your engagement, you can reveal all the lies you had to tell to cover your tracks.

If you are sending us a special item to place at the proposal location or want a message in a bottle, make sure you get the item shipped to us or write out your message. We like to have those ready about a week in advance.

Think of what you want to say when you get down on one knee. In order to get epic proposal photos, we ask that you stay down on one knee for at least 20 seconds. This gives us enough time to get close ups and a wide shot of the proposal moment. Even though it may be nerve wracking, try to practice your speech out loud so you’re not tripping over your words when it’s time.

You’ll also want to ponder what you want to wear. Consider that you should be comfortable but look nice in photos. Don’t forget to wash your clothes so you can pack them.

Pro tip: Many guys tell us they know their sweetie will want to be dressed up for photos but don’t know how to get her dressed up. If you wear something a little dressier and get dressed before her, she may pick out something fancier either subconsciously or on purpose to match your level.

Couple embraces while standing in the shore break on Maui

Use a thin ring box

Don’t use a bulky ring box from the jeweler. It’s too obvious in your pocket and will ruin the surprise.

We recommend getting a thin ring box or pouch and trying it on with your desired clothes to make sure it’s undetectable.

If you don’t have time to get a thin ring box, then put the ring straight in your pocket or the last resort would be to put it in a backpack. We don’t love the idea of putting the ring in a bag because it can get in the way during the proposal or be an eyesore in photos. If you decide to hold the ring in a backpack, make sure to put the backpack on the side so it’s not blocking your knee.

Thin ring box holding engagement ring

Do your homework

Once you book your proposal with Engaged on Maui, we send you a Proposal Guide and Dining Guide. Those were made with you in mind. Read them over when you receive them. If you don’t get them, check your spam folder. If it’s not in your spam folder, let us know. It means you aren’t receiving our automated emails and you will miss some important info.

About one week before your proposal after your final balance has been paid, we send your itinerary over. Carefully read through your itinerary and the email it came in. If your itinerary email came with a video walkthrough, watch that too. 95% of the time, the itinerary and video will answer any remaining questions you have about the plan.

Make dinner reservations

You should make dinner reservations as soon as you have your proposal date and time set. You can use our Dining Guide or check your favorite restaurant review sites.

If you have a proposal that is planned to end at sunset, we always recommend leaving a little buffer time in between the end of your proposal and your dinner reservations. Don’t make dinner reservations that force you to leave the beach right after sunset to get to dinner on time.

Once you’re engaged, you won’t be paying attention to the time. We’ve seen couples opt to hang out on the beach after we leave. It’s very likely you will be late to dinner if you have to rush, and most restaurants will only hold your table for 15 minutes before they give it away.

Picture-worthy hands

If there’s one time for a manicure, this is it. Your sweetie should have their nails done. If they get manicures regularly or will get one because you’re going on vacation, then you won’t need to worry about this.

If they don’t typically get their nails done, then maybe you can enlist a family member or close friend to invite them to get manicures before you leave. Or you can schedule a nail appointment on Maui if their nails aren’t photo ready when you get here.

Don’t forget about yourself. Your hands will also be in photos too, so take a little extra care of them before you get engaged.

Man's hand resting under woman's hand, wearing new engagement ring

These tips cover everything to do before getting down on one knee in Maui, except where and when to propose. For help with all your Maui proposal needs, contact Engaged on Maui today!

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