If you want to convince your loved one to vacation with you, you’ll need first to be your authentic self.  Be honest and open and remember to listen to any objections and be open to discussion.  Start thinking about ways that you can approach the subject of getting away together.

Light bulb drawn on yellow paper on corkboard


I remember when my husband and I planned our first vacation together.  We weren’t going far and it was a road trip.  We talked about where we would stay and what we would do.  Of course, he wanted to make sure that we didn’t break the bank and I wanted to make sure that we stayed somewhere nice.  He is more of a “wing it” person and I am a planner.  I want to know where my head will hit the pillow at night and he wanted to wait to get a room once we were at our destination.  I can tell you that we have had a couple of disasters using his method of choosing a hotel.



The first one was when we went to a small town in Arkansas.  We discovered that it was a weekend that people from all over the country came to shop at a huge craft fair.  We hadn’t done our due diligence and had no idea that this was going on.  The only room that was available was at a dumpy hotel and priced about 5 times too high.  So, needless to say, we spent the night in the car – believe me, the car was nicer than the last room available.  Ughhh.  Miserable for sure.


Messy room with a desk and lots of paper on it.


The second and last time that we used this “wing it” method was in Colorado.  Once again, most of the hotels were booked up.  We finally found a room in a pretty seedy area.  When we got to our “over priced” room, we discovered that it had blue and green shag carpeting from the 70’s.  The color palette was pretty bad, but, the worst problem was that the air conditioner didn’t work and was making all kinds of noise all while our feet stuck to the green carpet.  It was not only from the 70’s, but, it had probably been that long since it had been cleaned.  Lastly, there was a party going on at the pool (looked like a wedding reception of some kind) that was loud and went on until all hours of the morning.


Pool party at night


So that you don’t get stuck to the carpet or have to sleep in your car, here are some ideas to help you convince your significant other to go on vacation with you.


Discuss The Benefits


Start by explaining the advantages of going on vacation together.  How much fun you are going to have and the uninterrupted time that you will have together.  Point out how it can strengthen your relationship, allow you to have new experiences and memories, and create an opportunity to relax and unwind from everyday stresses.  Sometimes getting away from it all is enough of a benefit to convince your loved one to take that amazing vacation.


Choose the right timing


Timer that is white with black numbers


Make sure that your loved one is in the mood to talk and discuss things.  Make sure that both of you are in a relaxed mood and are open-minded. Avoid bringing up the topic when he or she is stressed or busy with something at work. Create a comfortable atmosphere for the conversation.  The last thing that you want is for one of you to be pre-occupied or stressed out about something.


Plan Together


Planner with pens laying inside it


Involve your boyfriend or girlfriend in the vacation planning process. It is said that planning a vacation is half the fun.  I agree.  Planning creates excitement as to what is to come.  A little caution though:  don’t be so rigid in your planning that if things don’t go perfectly that you fall apart.  Make sure to include a little “wiggle” room in your vacation planning.  Ask for his or her input on the destination, activities, and accommodations. This way, both of you will become excited about the trip that is to come.


Talk About Concerns


If your boyfriend or girlfriend has specific concerns about traveling or about going on vacation, listen to him or her carefully and attentively. Be authentic when you address those concerns.   After all, they may have a point.  Maybe it is something that you haven’t thought about.  Find solutions to those concerns. Whether it’s financial worries, work-related issues, or something else you haven’t thought of, try to find solutions together.  Make sure that your loved one feels heard and not just dismissed.


Focus on Shared Interests


Find activities or destinations that address both your interests. Maybe you are a shopper and he or she is into adventure sports.  Maybe you love fishing, but, your person loves art.  Make sure to highlight activities that fit both of you and that are available at your chosen destination.  Gather together maps or brochures that show your loved one some of the most attractive activities that fit their personality.  Be willing to compromise and enjoy their interests as well as your own.


Focus on The Positive


Be positive spelled out with scrabble pieces

Share stories vacations of to emphasize the positive experiences and memories created during trips. Paint a vivid picture of the fun and relaxation you can have together.  Think about purchasing a small gift for your loved one.  For a few ideas, see these gifts that I covered last week.  Offer to help create new memories and be ready to document those with pictures and maybe even a travel journal.  For me, I have started keeping a travel journal just to remind myself of the great experiences that I have had on vacation.  Memories fade, pictures and words do not.


Provide Solutions For Objections


If your boyfriend or girlfriend is concerned about work or other commitments, find ways to manage them during the vacation. Research if there are any remote work options available or propose a compromise that allows for both relaxation and attending to important responsibilities.  Even on cruise, my daughter recently connected to wifi and spent 3 or 4 hours finishing a work obligation so that she could still go on vacation.  Yes, it was a loss of 3 hours of her time, but, she had 5 days of relaxation once that obligation of work was taken care of.  There are solutions, you just need to be creative and help find those solutions.


Try To Be Patient And Understanding


I know that for me, if there is a pushback on vacation time, I get pretty upset.  I tend to let my emotions to take over.  But, that isn’t the way.  After all, remember that everyone has their own reasons and concerns about being away from home for any length of time. Be patient with your loved ones concerns and try to understand his or her perspective. Avoid pressuring or nagging, as it may have the opposite effect.  If you push too hard, you might notice major pushback.  Remember to accentuate the positive.  Sometimes it is best just to walk away and then come back to the subject once things calm down and your boyfriend or girlfriend has had time to think about things.


Talk About Your Commitment


Boyfriend and girlfriend holding hands. Closeup on their hands


Make it clear that going on vacation together doesn’t mean that you will neglect other responsibilities or relationships. Assure him or her that you value your time together and that the vacation is an opportunity to strengthen your bond.  Everyone needs rest.  Absolutely everyone.  Make sure to include some rest and relaxation into your trip and make sure that your loved one knows that you will include some of that much needed downtime.

Remember, to talk things over calmly, effective communication and understanding are paramount to reaching a decision that you both will be happy with. Be prepared for the possibility that your boyfriend or girlfriend may still not be convinced to travel.  But, with a little patience and some loving understanding, you will hopefully embark on a trip that will be long cherished and remembered.


Take a look at these paintings and photographs of Disney’s Boardwalk.  After all, Walt Disney World is a great place to take your loved one.  


Until next time!

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