6 Tips for Planning the Perfect Valentine’s Day Trip


6 Tips for Planning the Perfect Valentine's Day Trip

Last Updated February 2022 by Crystallace

If you could spend Valentine’s Day any way you wanted to and money wasn’t a factor, what would you? Let me know in the comments.

I know for me, the perfect Valentine’s Day trip would be me being surprised with a romantic vacation to the snowy mountains. Spending two weeks in the mountains, at a cozy resort just seems like the perfect Valentine’s Day. I have dreamt of this, I even have an entire Pinterest board dedicated to it.

BTW, are you following me on socials? Let’s keep in touch! I’m on Pinterest, IG, Facebook, YouTube, and TikTok

But back to reality, because while a Valentine’s Day trip may seem romantic if it isn’t done right it may lead to complications and disaster.

But don’t get nervous! It is possible to plan a Valentine’s Day Trip and have it turn out to be an amazing gift for both you and your partner, a memory that hopefully lasts you a lifetime.

6 Tips for Planning a Romantic Valentine’s Day Trip

1. Look at as Creating a Memory, Instead of a Gift

To avoid gathering items that ultimately become clutter because you don’t use them, more and more people are turning to creating memories, enjoying new experiences, and having fun when it comes to gift giving.

Valentine’s Day is no exception.

A trip on Valentine’s Day can be a great gift idea for both you and your partner but it will be most effective if you pay attention to the timing of the trip. This is important because work and family obligations can make it extremely difficult for one person to plan even a short getaway without at least some input from their partner.

Really think about it if you are planning a trip which is longer than a weekend, or falls onto a midweek night away. These types of trips will require you and your partner to take time off from work or to make arrangements for someone to take care of your home, children, or fur babies.

2. Plan Your Valentine’s Day Trip Together

If you don’t have obligations like taking leave, pets, or children then it’s easy to slip off for a night or two.

However, sometimes you’ll need to plan arrangements together. You don’t have to give away the whole surprise by telling your partner where you will be going but letting him or her know the dates of travel will help to avoid problems which could result if you do not consult with them beforehand.

3. Consider When You Should Actually Travel

Another thing to consider when planning a trip for Valentine’s Day is whether or not you want to actually be traveling on Valentine’s Day. This becomes especially important if you are planning a trip to a faraway destination.

If this is the case you might want to plan on either leaving after Valentine’s Day or before Valentine’s Day so you can spend the holiday relaxing together instead of traveling.

Travel can be very stressful and tiring so if you want to avoid problems which may result from this, it is a good idea to plan your trip so you will not be traveling on Valentine’s Day.

6 Tips for Planning the Perfect Valentine's Day Trip


When planning a trip for Valentine’s Day it is very important to make sure you select a location which both you and your partner will really be able to enjoy.

There may be a number of activities you want to do as well as a number of activities your partner enjoys but these activities will not necessarily overlap. However, there are likely to be some activities which you have in common.

It is important to make sure your vacation destination is one which will have plenty of activities for the two of you to enjoy together.

A buzzkill Valentine’s vacation would be if one person was really looking forward to a golfing vacation, but the other person does not play golf. It could result in the two of you spending a great deal of time apart during your vacation, rather than spending some romantic time away from the hustle and bustle of normal life.

By selecting a vacation where there are activities for the two of you to enjoy together you will be spending a great deal of quality time together on your Valentine’s Day vacation. Think of a sunset cruise, taking a nature walk, enjoy wine tasting – there are a million ideas you could think of.

Alternatively, if you both want time off from work and a frantic lifestyle and just want to relax on a deserted island somewhere and not lift a finger, then do that!

5. Ask yourself, what does your partner enjoy?

If this vacation is your treat, or if you are solely responsible for making the arrangements, think about what your partner enjoys doing. Putting in the effort this way means so much more to them than you could imagine.

Do they want to soak up the sun on a beach? Is hiking up the mountain more their vibe? How about cuddling up in front of a blazing fire inside a wooden cabin hidden in a snowy forest?

If you aren’t sure, try this. Order yourself a copy of The Five Love Languages (potential affiliate link). Make it a fun exploratory game where you and your partner can find out what the other’s Love Language is.

Then, base the trip (and all future gifts) around this result. It will all make sense once you get a copy of the book. And it’s an easy read that makes a lot of sense, too.

You won’t be sorry, and after taking the quiz, it will be hard for you to get the vacation wrong.


They say that getting there is half the fun. After all, it’s all about the experience, so make it a good one.

If you are driving to your destination, find out where there is along the way. Are there any roadside farm stalls that people say you simply have to visit?

Are you passing the world’s largest ball of yarn and you just must grab that shot for your digital scrapbook?

And if there’s nothing to stop and see, how about inventing a couple of cutesy car games for the two of you to play along the way.

The same goes for taking a bus, riding in a train, or even flying. Sitting and doing nothing can be mind-numbing – make it fun and laugh your way there!

Don’t Stress Yourself Out About This Valentine’s Day Trip

Don’t make Valentine’s Day a tricky holiday. Don’t stress yourself out and don’t be grumpy. This is a fun holiday and you should have fun planning it.

The best advice, honestly, is to plan in advance because there are millions of other people around the world who are going to be celebrating the same occasion as you, on the same day as you.

What tips and advice can you give about your past Valentine’s Day holidays? We’d love to know!

from the lawyer next door,
Crystallace Fenn

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Legal Disclaimer: Although I am a lawyer by profession, I am not YOUR lawyer. All content and information on this website is for informational and educational purposes only, does not constitute legal advice and does not establish any kind of attorney-client relationship by your use of this website.


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