Guide to Proposing on Vacation


December 30, 2021
Words by Be Inspired PR
Photos courtesy of

You’ve got the ring, you’re ready to propose, and you’ve decided what better way to pop the question than to ask during the epic vacation you’re planning – so now what?! Vacation proposals are always special; it’s a great way to make an unforgettable memory on a trip you’ve already both been looking forward to. But there are also some logistics to consider here, like keeping the ring safe during your travels, hiring a photographer to capture the moment, and planning the timing for the proposal itself, to name a few. We’ve gotten some help from the Be Inspired PR team to gather up expert-approved dos and don’ts to ensure your vacation proposal goes off without a hitch!

The DOs:

  • Propose at the beginning so you can relax. “When it comes to proposing on vacation, we highly recommend proposing at the beginning of the trip so that you do not have to keep track of the ring for longer than necessary! Also, after proposing, you will be so much more relaxed and can use the vacation to celebrate together, instead of being nervous the whole trip!” – Jamie, Cape Cod Celebrations
  • Work with a local planner. “OK, I’m biased here, but obviously the easy button is to work with a Planner local to the region you’re proposing in. Give them a budget, have a couple of phone calls to map everything out and let them work their magic. Planners can take care of hiring a photographer in the style you’re after, curating a florist for the vibe and aesthetic you’re looking to create, source live music, paper goods, catering, ensure your hotel room is set for celebration when you return…the list is endless.” – Ashley Lachney, Owner of Alston Mayger Events
  • Plan early to get the ring! “If you are thinking of proposing on vacation there are several dos and don’ts to follow to ensure your proposal goes off without a hitch! You will need THE ring to propose on vacation. It is best to get started on this process as soon as possible when you decide this is your time to propose. Visit several jewelers 6 weeks prior to your trip. After visiting several jewelers you can get a good feel for which jeweler you want to work with on such an important purchase. Make sure you get the ring underway at least 4 weeks prior to your departure to ensure you have it in time!” – Kaeleigh Testwuide, Founder & Owner, The Diamond Reserve
  • Make sure your ring is insured! “Before departing on your trip make sure you submit your ring’s appraisal to your insurance! You definitely want the ring insured while you travel with it.” – Kaeleigh Testwuide, Founder & Owner, The Diamond Reserve
  • Hire a professional photographer to document the event. “You’ll be so wrapped up in this whirlwind moment, that you and your partner will appreciate having these images to help you remember every sweet detail. You’ll need to book someone early, so this is a detail to plan a few weeks in advance of your trip. You can ask your hotel or resort for local recommendations, or simply Google to find a photographer with experience capturing proposals.” – Jenna Miller, Creative Director of Here Comes The Guide


  • Don’t stress! “Couples tend to want perfection for all things wedding-related but know that when traveling, obstacles often pop up that are out of your control. Remember to enjoy the process and roll with the punches if you have to, they are shared memories and experiences that you’ll (hopefully) laugh about in the future.” – Carli Fernandez, Founder, The Concierge Travel Group
  • Do not pack the ring in your checked luggage! “Make sure to pack it in your carry-on that you will keep close at all times while traveling. If you are worried about your baggage being opened up while at security and the ring being pulled out by TSA in front of your significant other there is a secret little trick. Put a piece of paper around the ring box with a rubber band around it, write on the paper clearly visible “This is an engagement ring, please open to view discreetly.” Put the box with the paper wrapped around it in a zip lock bag.” – Kaeleigh Testwuide, Founder & Owner, The Diamond Reserve
  • Don’t leave the ring once you get to your destination. “Prior to proposing, do not leave the ring in your luggage in your stay accommodations, keep it with you at all times in a bag that you take with you while traveling. This will help avoid any sort of theft. Plus, if you plan to be at the pool or swimming in the ocean you really want to think twice about leaving the bag with your ring in it unaccompanied while doing so.” – Kaeleigh Testwuide, Founder & Owner, The Diamond Reserve
  • Avoid outside pockets for storing the ring before you propose. “If you plan to propose later on in the trip be sure when traveling about that you do not keep the ring in an outside pocket of your bag. It is best to keep it in the main compartment of your bag or in a pocket in the main compartment. Be aware of your surroundings.” – Kaeleigh Testwuide, Founder & Owner, The Diamond Reserve
  • Don’t keep it a secret from staff. “If you’re staying at a hotel or resort, or having dinner at a nice restaurant, let the staff know about your plans to propose! They may have some tricks up their sleeve to make your day extra special—from a complimentary bottle of champagne or a special dessert to rose petals on the bed. Chances are they’ve had lots of proposals occur in or around their location, so they may be a wealth of valuable information during your proposal planning.” – Jenna Miller, Creative Director of Here Comes The Guide
  • Don’t tell friends or family ahead of time. “It can be so tempting to spill the secret to a few trusted friends or family members before heading out on your trip, but this could potentially lead to a disaster! Every text, Instagram post, or phone call that your partner sends out will be watched closely by those you’ve told at home as they wait for you to pop the question – and they might end up spoiling the secret with a few too many “anything exciting happen today?!” questions! Save the surprise and they’ll just be thrilled when you announce you’re officially engaged!” – AJ Williams, Founder & Creative Director, AJ Events

Photos courtesy of (in order of appearance): Lisa Elizabeth Images (1st); Katy Weaver Photography (2nd & 3rd)

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