Guide to: Proposing on Vacation – What You Need to Know

In this article, I’ll explain how I proposed to my girlfriend on our most recent trip to Indonesia. If you’re going to try proposing on vacation and need some advice and tips, this is a must-read!


I am fairly certain that my tips here have some validity due to the fact she said YES! But I can’t promise you the same. So if she says no, please don’t fill our site with hate mail. With that being said, let’s dive in!

Taking the Plunge

First things first…

You and your significant other are very much in love and have spent a lot of time together and all that lovey-dovey stuff. But if you are planning on proposing you need to be CERTAIN that she/he is the one you want to spend the rest of your life with. With the number of divorces that occur today in the world, you need to make sure that you sit down and take the time to really make sure you are ready for this. If you have done this, then continue on.

Planning the Vacation

Obviously, if you’re reading this article you’re interested in proposing on vacation. So with that being said you need to make sure you have a vacation booked. Now whether you and your significant other planned a trip to California to travel the coast or booked a bungalow for a week in Bora Bora, make sure that wherever you have picked to go on vacation is a special place for the both of you. My now fiance and I obviously love traveling the world so our last trip was booked for Bali, Singapore, & the Maldives. I knew this was my moment… c’mon not a lot of people can say they got engaged on Gili Air Island in Bali. Now that’s exciting!

Buying the Rock

Buying, or even shopping for a diamond could start to get a little overwhelming. There are a ton of articles on the internet pertaining to guidelines for buying an engagement ring. One bit of homework you need to do before even looking at rings is to try and find out what type of ring she likes. As far as the shape, design, band, estimate size, anything you can. Luckily for me, my GF told me almost everything I needed to know just in case I ever wanted to commit (crazy, I know).

I am a big fan of purchasing things online so I thought to myself, “Could I do this with a ring?” People may say this is sketchy or even tacky but the world is different now and, to be honest, there is such a wealth of information on the internet regarding rings and education on buying online. but if you choose to do it the old fashion here are a few tips about how to buy an engagement ring for guys:

step 1: determine your budget.

Step 2: Follow her friends and.... stalk Pinterest

Step 3: Determine Her Style

Step 4: Determine her ring size

Step 5: Begin shopping Step 6: Make a decision (and buy!)

Step 7: Get it insured!

Step 8: Arrange the perfect moment.

If you chose to shop the web for the best prices, a tool that I found really helpful was a website called RareCarat. They pretty much filter all of the online diamond jewelers that are reputable and you can compare prices per diamond, size, carat, color, cut, etc.

at Rock!!

Planning Your Execution

You came a long way. You made the commitment, planned a vacation, bought a rock… Now how are you going to drop the knee (propose)? You could do it at dinner, hell you could do it on the plane if you wanted, but this is a once-in-a-lifetime (hopefully) opportunity to make this event even more special for that person. So my advice would be to find a special place, event, or something that stands out where you are going. For example, I knew that we were traveling to Gili Air Island off the coast of Bali, Indonesia on February 13th, so I researched on the internet some special places and things to do on that island that would stand out. I came across the infamous Gili Swings, a special place that people travel to these islands specifically to take pictures of and check out. Wherever you are going, take some time away from your fantasy leagues and research a little about your destination and where you can drop that knee!

Planning a Little Something Extra (Bonus Points for Sure)

Everything is all set up in your head and your diamond is being shipped from whatever company you chose. You chose an awesome spot to pop the question. She’s going to be very excited and surprised. This is the big day she’s always been dreaming of. What better way to always remember this special moment than to have…You Guessed it! Pictures! This may seem like a no-brainer but I’m just making sure you take this step in your proposal planning seriously.

You have two ways to go about this depending on where you are traveling. 

  • If you are going to an excellent all-inclusive resort in an established resort area, chances are if you google photographers you are sure to find some in that area that is reputable. However, they may be pricey. You only need an hour or two of their time to capture this proposal and maybe a quick engagement shoot after. The hotel or resort you are staying in may even have its own event photographers or people they would recommend, so be sure to shoot them an email and ask.

  • Another scenario you may encounter if you are planning this maybe in a more remote location (cough cough Gili air Indonesia) would be to find freelance photographers. These guys can offer great value and do a great job. Just make sure to ask them a few questions and request to see some prior shoots on Instagram or Facebook. It may be possible to find these freelance guys on Craigslist or some other local job posting website.

Great Tip:

If you haven’t found anyone you really like on any websites go to Facebook and search for:  “Buy/Swap/Trade *Insert Destination*”.  Once accepted to this group a lot of times if you search inside the group for photography or photographers you will get a ton of great people. This is the method I used to find an amazing photographer!

The Day Of


I know it seems like you’ve covered everything and you haven’t done this much planning in your life, but there are a couple of additional things you should consider. The time of day, bright and early or during the sunset? What will you do for the day prior to popping the question? Do you need to meet with the photographer during the day? I needed to meet with my photographer, Al at 4 pm that day so I knew I needed to ditch my girlfriend, so I dropped her off to get a massage so I could accomplish this. Also, what will you be doing after you drop the knee? Do you have dinner reservations? (Good idea). Plan all of this out to the best of your ability.

Useful Tip

Make sure when traveling with a ring that you keep it in your carry-on baggage. A good idea would be to keep it in the box and put that box into something like a sock and stuff it deep into your backpack or luggage. You could also put a note on it saying engagement ring so if the Airport Security does go through your things they won’t ruin the surprise. Also, be prepared to give them “the eye” and a whisper if they are rummaging through to get to it. Maybe encourage your girlfriend to go sit down and wait for you.