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How To Propose While On Vacation

Men are getting more romantic when it comes to dropping down on one knee. The latest trend when it comes to popping the question is planning a destination proposal. Nothing says romance like getting away together, alone, in some remote corner of the world. Or maybe she would prefer being proposed to in front of Cinderella's Castle at the Magic Kingdom. No matter where you choose to propose, it will be romantic, especially if it is something she enjoys.Surprising her with an engagement ring while on vacation takes a lot of planning. Planning a destination proposal means researching destinations, making travel plans, finding a ring and so much more. Knowing what she likes will make the planning much easier, because you will be able to plan your vacation and that special moment around her likes. This will ensure she will remember the moment forever.
Propose at Walt Disney World (Credit, Heather Leigh Carroll)

Popular Destination Proposals

Men have been proposing for centuries. Some make it simple, while others go all out. Choosing to propose while on vacation means you put some extra time, effort and planning into the proposal. Below are some of the more popular destinations for couples to get engaged:

  • Cruises: There are many romantic options aboard a cruise ship or one of the exotic ports of call.
  • Paris: This destination is home to many romantic fountains and the Eiffel Tower, all of which are perfect locations to propose.
  • Tropical Resorts: An all-inclusive resort in Jamaica or Hawaii offer tons of romantic possibilities.
  • Venice: The canals of this area are very beautiful and offer the perfect backdrop for a proposal.
  • Big Cities: New York, Chicago and San Francisco have buildings with great views of the sunrise, the sunset and the lights of the city, which can be very romantic sights.
  • Castles: There are many castles located throughout Europe, all of which have unique architecture which makes for a romantic backdrop.
  • Walt Disney World: If she is a Disney fanatic, there are carriage rides, secluded lagoons, flower gardens and, of course, Cinderella's castle, all of which will offer perfect opportunities to propose.
  • Sunset at the beach: Find a secluded area of the beach for a romantic stroll hand-in-hand.
  • Extreme: If she is not your typical romantic, consider proposing while skydiving and scuba diving.
When She Knows About The Trip

How you handle the engagement will also greatly depend on if she knows about the trip you are planning or not. Here are some tips to help you pop the question if she knows about the getaway.

Plan everything out before you leave. Do not wait until your arrival to start planning where, when and how you plan to propose. Determine if you will do it at sunset, while at dinner, at the beach or just out and about during your romantic escape. Call the hotel's concierge desk for help with planning, such as making dinner reservation and having flowers delivered to the room for when you return.

Chances are she is hoping you will propose during the vacation. Make her wait. If possible, wait until the last day of the vacation or somewhere in the middle. Avoid proposing on the way to the airport or the minute you check into your room.

Remember, no matter how much planning you do, there is a chance something will go wrong. The restaurant may be closed or the area you selected might not be what you really wanted. Have a backup plan, just in case something goes wrong and what you originally planned for is no longer available or suitable for proposing.

Keep track of the engagement ring so it does not get lost while traveling to your proposal destination. If driving, make sure it is securely packed in your suitcase, not the one your are sharing, or lock it in the glove box. If you are more comfortable, keep the ring in the pocket of the jacket you are wearing. That way you know where it is at all times.

If flying, pack the ring in your carry-on luggage. Do not carry the ring on you because you will have to take everything out of your pockets when going through security and it might spoil the surprise. Fill your carry-on with other items that will not call for a closer check of the bag, such as clothing and books. If possible, put the ring in something besides the ring box. This way it will not be obvious if your bag is pulled for a closer check through security.

Propose on the beach (Credit, Heather Leigh Carroll)

When She Has No Clue About The Trip

It will take a lot of work to plan the entire trip without her knowing, but it is possible. Do some research and select the perfect destination. Popular surprise destinations include a luxury hotel overlooking the bay or a Caribbean beach resort. It is important to select a destination you know she will love.

Clear her schedule so she is free to go. Without her knowing (if it is possible), check with her family, friends or boss. Find out if she has any plans or deadlines for the timeframe you plan to surprise her with a romantic getaway. To avoid the cat being let out of the bag, enlist only one person to help you find out this information.

When it comes to packing for her, you can do one of three things. The first is to attempt to pack for her. This may require some additional help from the person you enlisted to help clear her schedule. The second is to make a game of it and have her pack. For example, tell her she has only 30 minuets to pack for a three-day getaway to somewhere tropical. The third option is to just leave and take her shopping once you arrive.

Related: Best All-Inclusive Tropical Family Vacations

When She Says "Yes"

After you have dropped down on one knee and she has said yes, it is time to celebrate. If you are enjoying dinner, tell your server, because some restaurants offer a champagne toast or dessert for couples who have just gotten engaged.

Have something special planned for when she says yes. For example, have the concierge place rose petals all over your room and have chocolate-covered strawberries and champagne delivered to your room.

If She Says "No"

This is unfortunate, but there is a chance she could say no. However, if you are planning this vacation getaway, chances are she is already aware you are planning on asking her to marry you, so it is very unlikely she will say no.

Should this occur, do not let it get in the way of your vacation or waste time discussing why. Move forward and enjoy what time you have left at your destination. Continue exploring sites together, but know that there will probably be a discussion when you return and your relationship will either end or remain at a standstill.

A lot of planning goes into proposing while on vacation. There are a lot of secrets that need to be kept, but in the end, it will be worth it. Before making all of the plans for a destination proposal, make sure you are really ready to propose and near 100 percent sure she will say yes. This will make the getaway less stressful and more enjoyable for the both of you. After she says yes, take some time to relax before returning home. Because when you return from your getaway, the two of you will be busy with all of the wedding planning.

Related: Travel Guide for Honolulu's Waikiki

Heather Landon is a freelance writer with more than 20 years of experience. She has combined two of her passions - writing and travel - to share her experiences with others. You can read more of her articles at

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