Newly engaged fiance holding thin ring box that contains her engagement ring

If you’re questioning when you should propose during your Maui vacation, this article is for you!

For some, their proposal date is a no-brainer. There is a day that is special to their relationship or one that naturally works better.

For others, the date is flexible and picking a date is one of the first choices they need to make before getting down on one knee.

Pop the question earlier in your trip

Couple dancing in the forest after engagement

Most of our clients will opt for proposing on the first or second full day they are on Maui. We highly recommend popping the question sooner rather than later for a few reasons.

First, you’re likely going to be nervous leading up to the big moment, so once you propose – and they say a big YES! – you’ll be able to let out a sigh of relief. Then the two of you will be able to spend the rest of your Maui vacay celebrating!

Getting down on one knee towards the start of your time on Maui also might be better for your photos. Many people don’t realize how strong the sun is here and end up with a bad sunburn.

Due to Hawaii’s proximity to the equator, the sun’s rays are much stronger that what you might experience at home. This means, you can get sunburnt on an overcast day, even when it doesn’t feel hot.

It can be really tough, not to mention painful, to cover up sunburnt skin with makeup. It’s even trickier to mask red skin in Photoshop. Picking a proposal date towards the start of your trip will help prevent the chance of having a horrible sunburn in your proposal photos.

Lastly, an earlier proposal date gives us extra leeway in case we need to reschedule for some reason. Although it’s rare, there are times when we had to or were considering rescheduling for reasons beyond our control. You probably don’t want to propose when it’s pouring rain or there’s a hurricane warning. When weather isn’t cooperating on your original date, it is nice to have options for a backup proposal date.

But don’t propose on the same day you arrive

Maui sailboat proposal

With all the reasons to propose early in your Maui vacation, you might be tempted to pop the question as soon as you get off the plane. However, we actually have a policy against planning proposals on the same day you arrive. It’s too easy for something to go wrong that would cause you to miss your proposal. The reason why we have this policy is because we’ve learned from experience.

What if your flight is delayed? What if you get into a car accident or get stuck in an elevator before you get to the airport and miss your flight? (Not wishing this upon you, but these things have all happened to our clients, causing them to not show up when they were supposed to propose.) What if it takes you longer than expected to get your bags at the airport and get your rental car? What if your sweetie is too tired or doesn’t feel well after traveling and doesn’t feel up to your plans?

Like we said, it’s too much risk that can all be avoided by planning your proposal after your first night here.

Avoid weekends and holidays if possible

Sunrise beach proposal in south Maui

If you’re dreaming of proposing on a beautiful Maui beach, we definitely suggest you avoid choosing a holiday or weekend if at all possible. Beaches are going to be much busier on those days. Locals like to enjoy the beach too (it’s one of the reasons why we live here), and weekends and holidays are usually the days when we can hang out at the beach with our families and friends.

Since we can’t ask anyone to move to a different spot or leave the beach, even if we get there first, it’s safe to assume you’ll have lots of other beachgoers present if you’re choosing to propose on a Saturday, Sunday, or a holiday.

For example, a Valentine’s Day proposal can sound really romantic, but keep in mind that there will likely be beach weddings happening and other proposals too. At Engaged on Maui, we never schedule two proposals on the same beach on the same day, but that doesn’t mean we can stop other people from planning their own proposal.

The exception to this rule is proposing on the beach at sunrise. Even if it’s on a weekend or holiday, there’s a decent shot you’ll have the beach to yourselves if you’re willing to get up early. The good news is that many visitors say they rise before the sun on their first morning in Maui anyways due to the time difference.

Use a special day to you

Couple embracing with man behind woman, putting his arms around her shoulders and her holding his forearms

Sometimes, using an anniversary or birthday can be helpful in keeping the surprise. Your other half is already expecting you to make special plans, so it doesn’t seem as suspicious if you say you want to visit a certain landmark or made reservations at a nice restaurant.

Others may feel that their partner is expecting them to propose on a certain date and purposely pick a different one in order to throw them off.

You know your sweetie best, but we can always weigh the pros and cons with you on certain dates.

Work around your itinerary

Maui proposal in front of palm trees

When your other half is the planner in the relationship and has packed your vacation with activities, we may have to plan your proposal date around the little openings you have in your schedule.

The best thing to do in this case is send us a copy of your itinerary and let us give you ideas that would fit seamlessly into your existing arrangements. We can look at where you’ll be and say, “Okay, you have dinner reservations at this restaurant. You can propose at this beach on your way. Or you’re going on this hike, we have these locations nearby…”

We’ve worked with clients like this and there have been times when they didn’t love the options that fit into their existing schedules. However, we helped them find a spot they did love and then they worked out how to convince their sweetie to change the plan to accommodate their secret proposal.

We pick the date for you

Showing off ring after surprise proposal

There are occasions, especially during busy season or with last minute proposal inquiries, where our calendar is extremely full or the venue you’re interested in is completely booked.

In these circumstances, you have to pick from our limited time availability and/or location choices, which could be less than ideal. That time could clash with what you already have planned or mean you’re proposing at the end of your trip. If the location you want is unavailable, because it is also a wedding venue that gets reserved many months or over a year in advance, we know it is a letdown.

To have the full pick of date and location options, inquire with Engaged on Maui early! We’re talking as soon as you’ve booked your trip or even before you’ve officially paid for your flights and are just considering getting down on one knee in Maui.

We’ve planned hundreds of Maui proposals and will be happy to help you choose the best day to ask your partner to be yours forever!

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