Nothing could be more romantic than a magical proposal vacation – we’re convinced! And, we’re here to prove why with a few bonus tips on how to plan the perfect destination proposal, as well as some unique ideas just for you.

Just imagine, you and the love of your life, lying on a white sandy beach looking out onto the clear blue sea with a couple of cocktails beside you. Yes, this fantasy could become your reality with just a few clicks and a bit of planning! Flying over to the Caribbean is a lot easier than it may seem, and also cost effective depending on the time of year. It’s all up to you…so let’s make it happen.

Here are some original ideas to help get your creativity going:


Take your significant other for a romantic tour to El Piton in St. Lucia. You can hire your own private boat, and organize a special dinner with just the two of you and pop the question on the way! The views are a true sight for sore eyes, and the experience will be that much more memorable.


Ask them to marry you at the airport right before your flight. They truly won’t expect this amazing surprise, and better yet, you can even invite the family to be there to celebrate with you. Chances are they will say yes, but only choose this option if you’re pretty certain, because this method will put a bit of pressure on them for the big fat “YES!”


Nostalgia wins every time. Take them on a surprise trip to the first Caribbean island that you two went on for vacation. During the conversation at dinner one night, tell them, “ For all the trips that we’ve ever taken together, and for all the precious memories that we’ve shared, this one will forever be my favorite. Will you marry me?”


Skywriting is always a yes. If it’s one thing that they won’t expect on a vacation, it is this! Hire a company to sky write “Will you marry me” or get a plane to fly a banner with the sign “Will you marry me?” over one of the most stunning beaches where you choose to stay. Each Caribbean island has endless gorgeous beaches to enjoy, so take your pick at Tobago, Jamaica, The Bahamas, or even Dominican Republic. You won’t be disappointed.


Sand writing could be even more amazing! You’re at one of the top destinations for honeymoons in the world, known for its luxurious hotels, nightlife, and of course beaches! Have a special day planned prior to your arrival to the hotel, and get that “Will you marry me?” sign written in the sand on the day that you decide to pop the question. You can even line the pathway to the sign with rose petals or their favorite flower to build up their excitement.


  • Ring Care is #1! Whatever you do, ensure that the ring is carefully stored in your carry on bag for safekeeping. Yes darlings – your carry on bag. Please do not put the ring on your person as to prevent any mishaps at the airport security checkpoints, as well as throughout the plane ride or rides. You won’t want to have arrived at your dreamy destination with no ring in hand! So take note of this first and foremost.
  • If they know about the trip already, then this will give you an opportunity to plan with the hotel prior to your arrival with ease. Arrange for a nice luxurious dinner, and even a possible walk along the beach at sunset. If your S.O. is a flower lover, then throw in a little rose petal love on your bed in the shape of a heart, and maybe even a bottle of bubbly for that little extra touch. This will open up the setting possibilities and get them even more anxious for what’s to come.
  • Since the Caribbean is already the PERFECT destination for your proposal, being unique is key. Soak up the sun on a luxurious day cruise, go snorkeling at Jamaica Dunn’s River, or take them on a sightseeing tour of Santo Domingo in Dominican Republic. There are hundreds of options at your disposal, to create even greater memories for you and your S.O., so be as creative as possible and remember to choose an activity or location that you know that THEY will love.
  • Clear their work schedule. Getting in touch with their boss (if they have an 8-4 job) is very essential to your master plan. But whatever you do, try to inform only one or two people, to prevent word of mouth on your proposal plans. Let their boss know at least two to three months in advance of where you would like to go, and for how long and then plan accordingly. If you must, then confide in one other person (your middle man) in cases where getting through to management may be a bit challenging.
  • Pack their bags and head off! Now this one is also quite tricky, since packing for you could sometimes be a serious chore. But, this is a MUST if your S.O. isn’t in on your travel plans. Contact a close friend or relative, and get to work on their suitcases. Pack the essentials, the daily wears, and of course, the formal outfit that they may need on that very special night (options encouraged).

At the end of the day, this entire process truly boils down to you and your partner. If you know that they are the quiet, simple type and would prefer a nice home cooked meal instead of all the travel details for their proposal, then choose that option and make it the best intimate experience ever. But, if your partner is down for the adventure and loves an out of the box surprise, then a destination proposal in the Caribbean is for Y.O.U.!

Whatever you decide, have fun. Oh, and Congratulations – You’re Getting Married!

Getting ideas for your Destination wedding could be tough. Make it a little easier with some sweet inspiration. 

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