You are ready to take your relationship to the next level. You bought a beautiful engagement ring, obtained the blessings of your partner’s parents and booked your trip to Grand Cayman… And now what??? 

As a professional engagement and elopement photographer in Grand Cayman, I often get asked for advice at this stage of the “process”. In this blog post I am sharing some helpful tips that I’ve learned from my happy couples to get you prepared for the perfect surprise proposal: 


01 I Be Well Prepared 

A surprise proposal isn’t something to slap together at the last minute. It has to be carefully orchestrated so that every part of your scheme works, including keeping your partner in the dark until the last minute. Your planning and preparation can make the difference between mediocre and an outstanding experience and when it comes to something as significant as how to plan a surprise proposal – one moment in life that alters all the moments that come afterward – you will want to be sure that every aspect of the experience is filled with the same magic you feel for your partner.


02 I Decide on the perfect location. Grand Cayman is certainly one of those places that is so incredibly beautiful that just being here can set the perfect mood and context for your proposal. Especially the beautiful beaches in Cayman make for the perfect proposal backdrop! I am a big fan of photo locations with stunning natural beauty, which we have some of the best in the world here in Cayman. Here are 5 examples of beautiful proposal spots on the island:

(Please go the bottom of this post to see picture examples from some of the different locations. Not all of them are included so please feel free to ask me for more references and take some time to google images of the different location… I have included the Google map links for your convenience too)

  1. Seven Mile Beach: One of the most iconic places on the island (Pro: you get the beautiful turquoise sea. Con: it can be a little more crowded). To escape the crowds I usually shoot further up towards West Bay. There is also a dock in West Bay, if that is something you would like to include in your photos.
  2. Spotts Beach: This beach has a beautiful dock and lots of variety with the beautiful rock formation and many palm tress (Pro: its generally less crowded during sunset time, it has dock and beautiful rocks. Con: The sun doesn’t set right there but behind the mountain during the summer months, so you are not always guaranteed to see the full sunset.
  3. South Sound Community Beach – also known as Surfer’s or Consuelos beach. This is one of my favourite beaches as it is a little more “rustic” and secluded (Pro: less crowded, beautiful rocks, a little more off the beaten track, sun sets right there. Con: water is not as turquoise and there are more waves).
  4. Smith’s Cove (Smiths Barcadere): Smith’s Cove is another iconic beach/cove on the island (Pro: It has a beautiful cove as well as ironshore. Con: it can be a little more crowded and wave if the sea is a little more rough).
  5. Cayman Kai / Sunshine Point: This beach is on the North Side of the island close to Rum Point and Starfish Point. If you are staying on that side of the island this is a great option for you (Pro: it is a totally secluded and huge empty part of the beach with some lovely palm trees and lovely greenery close by at Starfish Point. Con: It is far away if you are not staying on the North Side).


03 I Get the timing right… You will most likely be on vacation in Grand Cayman, which typically limits the dates you have to chose from. However, when it comes to the time of the day, the best time is undoubtedly just before sunset! I am sure you would agree that it doesn’t get much more romantic that a beautiful beach walk, ending with a surprise engagement proposal as the sun sets in the background?! 


04 I Get your partner looking his/her best
Most people prefer to have the opportunity to prepare themselves for a photo shoot. Staging a romantic photo session that turns into a proposal shoot, the moment you pull out the engagement ring is a great way to go. This will ensure that the love of your life is looking his/her best, without spoiling the surprise in your proposal. Another way to be sure that attire and makeup are camera-ready is to tell him/her that you are taking them to a special event or exclusive restaurant. 


05 I Ask Your Photographer For Help
It really helps bringing your photographer into the picture early on in the process so that I can help  you create the best setting and get the perfect pictures without ruining the surprise… Here are 3 different approaches that help keep the surprise a surprise and still get your special day documented perfectly… 

(By the way, these are examples of things I have actually done for couples in the past and know they work!)

  • I can pretend to be your tour guide / driver taking you to a special location and as a value add taking a picture of the two of you, which is your cue to get on your knee. 
  • You can tell your partner that you have hired a photographer for a romantic portrait session for  the two of you, which would allow your partner every opportunity to properly prepare for being in front of a camera without spoiling the surprise. 
  • I can hide amongst the palm trees paparazzi style or pretend to be photographing the scenery or another couple until you are ready to pop the question.

You know your partner best so if you have any other ideas… don’t hesitate to bring me in on your planning and I will do whatever I can to make it perfect for the two of you!

We will also agree on how and where it is best to stand to get the ideal angle and agree on some secret cues that signal to me that you are ready to pop the question and my camera is ready!


06 I Looking for something more grand? Get some undercover help!
It can be very difficult trying to coordinate a special surprise so far away from home and most often in a place that you have never been to before. Or maybe you’re all about grand gestures or you believe a marriage proposal deserves something more creative. Whatever your situation, you’re going to need some undercover help in pulling this surprise off. This is where Direction Event Planning comes in… Amanda from Direction Event Planning specialises in bespoke engagement and elopement planning and coordination. She can help you create the perfect little beach setting with rose petals and champagne or a private dinner on the iron shore. Your imagination has no limits here and she is the perfect partner to execute it all for you, so “all” you need to do is show up and pop the question. 🙂

Should you have any questions or ideas about your upcoming proposal, please don’t hesitate to contact me, so I can help you plan and document the perfect surprise of a lifetime!)

Surprise Engagement Proposal, 7 Mile Beach, Grand Cayman


Still Unsure?  Here are some reasons why you should hire a professional photographer to document your surprise proposal…



01 I You can look back on the precious memories.

Right after their loved one pops the question, most people experience a mix of emotions and will likely tune out their surroundings. Since you will be too busy admiring the new ring and soaking up every second of this precious moment you might miss some other details. Hiring a photographer allows all the details, such as the raw emotions and beautiful backdrop, to become captured forever.


02 I You can use the photos on your wedding stationery.

Proposals are full of love and raw emotion, making for extremely touching photographs. Also, once the engagement part is done, we will do a full couple portrait session, making for a great image library for all occasions. You can take full advantage of the images by using them for save-the-date / wedding invitations, websites or even Christmas Cards.


03 I Loved ones can share in the moment.

After getting engaged, your family and friends will ask about the intimate details of the proposal. Professional photographs will serve as a handy visual aid here. Showing pictures of your fiancé’s rose petal pathway is much more impactful than trying to describe it. Plus, I always make sure I send you a small selection of my favourite images the very next day so you can send it on to your family and friends or post on social media. 


04 I The photographer will help make your vision a reality.

As photographers we have a trained eye, so we will be able to help make sure the proposal looks great in an image. Since I have done this many times in the past, I will help you make sure that everything goes off without a glitch!


To see some more Pros and Cons, check out Martha Stewart’s wedding blog.


Lisa Reid Photography Cayman Enagement Photographer
Kimpton Seafire Surprise Proposal, 7 Mile Beach
Lisa Reid Photography Cayman Enagement Photographer
Ritz-Carlton Surprise Proposal, 7 Mile Beach

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