At Engaged on Maui, we’ve planned hundreds of proposals, and if there’s one thing we’ve learned—it’s better to be prepared. Maui’s tropical beauty comes with a few unpredictable elements (wind, waves, and the occasional rogue mosquito), so here’s our tried-and-true list of what to pack for your proposal just in case:

Bug Spray

You’re in paradise… and so are the bugs. Especially for beach or garden proposals, a quick spritz will keep the “ouch” out of your romantic moment.

Small Towel

Whether you’re wiping off sweat, brushing off sand, or dealing with a happy tear overload—this one’s a lifesaver. Bonus points if it fits in your back pocket.

Water Bottle

Stay hydrated! Maui’s sun is no joke, and a bottle of cold water will keep you feeling good and looking fresh in your proposal photos.

Safety Pins

Wardrobe malfunctions, meet your match. You never know when you’ll need to secure a stray strap or tag that’s popping out mid-photo.

Makeup Blotting Paper

Perfect for beachy proposals or warm afternoons—blotting paper keeps you both shine-free and photo-ready.

Breath Mints or Gum

Because you’ll want that kiss after the “yes” to be minty fresh.

Fully Charged Phone (on silent!)

You might not use it during the actual moment (especially if we’re capturing it for you), but having it on hand to call your family after? Essential.

Extra Hair Ties or Bobby Pins

If the wind picks up, these little lifesavers can help keep everything in place—especially for long hair.

Bonus Tip: Let us carry the stress so you don’t have to. At Engaged on Maui, we help plan and photograph surprise proposals all over the island, and we’ve got backup supplies (and backup plans) ready to go.

The post The Proposal Emergency Kit: What to Pack (Just in Case) appeared first on Engaged on Maui | Maui Proposal Photographer.

Congratulations from your family

Having your new fiancé read messages of congratulations from your family is such a special way to start off this next step of your future together. Of course, you’ll probably get text messages and comments on social media once you reveal the big news, but going old school with hand-written congratulations shows you really put some extra thought into, not just your proposal, but afterwards too.

You could have your family members all sign a card and give your new fiancé this card after they say yes. If your family lives all over the place and signing one card isn’t feasible, each of them could mail you a letter or card by a certain deadline before you leave.

To prevent any suspicion, you can have the letters mailed to you at work. Or you could ask another family member or close friend to keep them safe for you until you’re ready to pack the cards into your suitcase. If it’s too risky to pack them, you can also mail your family letters directly to us.

This does require some advance planning, but if you have time to do this, it will be such a sweet gesture welcoming them to the family.

For Lawton and Maddy’s proposal, we took our message in a bottle add on and changed it to incorporate Lawton’s family. Normally, we use a message in a bottle before the proposal. You write a message on it for your sweetie to read right before you get down on one knee.

This time, we gave Lawton and Maddy the message in a bottle after the proposal. Lawton’s mom was in charge of getting family members to write messages of congratulations on a scroll. She mailed the scroll to us. We put it in a bottle and gave it to their photographer so Maddy and Lawton could read the messages while she captured their reactions.

If your family prefers talking to writing, another thought is to have them send you videos of them giving you well wishes that you can watch together after the proposal. Since this is likely to take a while to watch, we recommend playing the videos when you are back in your room, instead of during your photo session.

Presents after your proposal

A classic way to celebrate your engagement is with a bottle of champagne. If you’re staying at a resort, it’s easy for family to call and order a bottle to be delivered to your room. If you’re staying at an Airbnb or somewhere without a front desk or room service, then we may be able to help deliver the present during their photo session.

We love how Francis’ family contacted us to add champagne with a little note to his engagement session with Brianna. You can see their story here.

If your loved ones want to put a Hawaii spin on their surprise, leis are a beautiful addition to your photos.

Tony’s sister Brenda lives on the island of Oahu and worked with us to help plan his proposal to Katie. She wanted them to have beautiful leis after the proposal. Brenda purposely picked specialty leis that you can’t just find in the grocery store – maile intertwined with tuberose for Tony and a white orchid and pink rose lei for Katie.

Using technology to bring family to you

If your sweetie is super close to someone who won’t be there for the proposal itself, you can go above and beyond by calling that special person right before the proposal and putting your phone in your pocket. After the proposal, you can reveal that special person was “there” the whole time. Mikey introduced us to this idea when he proposed to Caitlin with her mom on the phone in his pocket.

If you decide to do this, put your phone in your back pocket or somewhere it won’t be bulky and distracting in photos. Do a test run by calling the person, sticking your phone in the pocket you’re planning on using, looking in the mirror to ensure it doesn’t create an unsightly bulge in pictures, and confirming they can hear on the other end.

You can also FaceTime loved ones after the proposal. Just keep in mind that any time you spend chatting will be taking away from your photography time, so you’ll want to keep it short or save the FaceTime for when you don’t have anything to do or anywhere to be.

You’ll also want to double check the time difference as it may be very late where relatives live. We’re 5-6 hours behind EST depending on the time of the year, so it could be midnight when you’re calling.

Conclusion

Your engagement is an exciting time, not just for you two but for your friends and families as well. We hope these ideas will inspire you on how you can incorporate your nearest and dearest when they won’t be here for the proposal in person.

If you have any new ideas on how you want to involve family in your proposal, we’re all ears! The sooner you contact us to start planning, the better!

The post How to Involve Family in your Destination Proposal – Part 2 appeared first on Engaged on Maui | Maui Proposal Photographer.

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

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

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

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

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

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

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!

The post How to Choose Your Maui Proposal Date appeared first on Engaged on Maui | Maui Proposal Photographer.