How To Have An Amazing First Vacation With Your Boyfriend

Like many relationship milestones, going on a vacation with your boyfriend for the very first time is one that you will remember forever! Here's how to make the best of it!

Thanks to celebs, movies, and our favorite TV shows, we have an idea of what we want our first vacation to look like, and what we definitely don’t want it to look like. Take Kim Kardashian, for example.

When she brought ex-husband, Kris Humphries, on her family’s vacation, she showed him sides of her that weren’t so pretty: freaking out over the huge room they got and losing her sh*t when she lost one of her highly expensive diamond earrings in the water, among other things.

Or, on The Mindy Project when Mindy realizes that she’ll be in a hot tub with her new boyfriend Cliff… in the middle of January (oh, the horror), and she feels the urgency like we all do to magically lose ten pounds just like that.

So, as you can see, a vacation with your beau (especially for the first time) isn’t just all sand, sun, romance and fun. On the contrary, it can mean bad sunburns, terrible hangovers, bad fights and only one bed to sleep in. So to avoid all that and make memories that you’ll actually want to remember forever, follow these must-know tips for having an amazing first vacation with your boyfriend.

So to avoid all that and make memories that you’ll actually want to remember forever, follow these must-know tips for having an amazing first vacation with your boyfriend.

Plan it out together

Happy couple with globe choosing place for travel

When it comes to shelling out thousands of dollars for a vacation, planning is key. No question should be off-limits, especially ones like, what’s your budget? Do you prefer sunny or snowy? A place you have to fly to or drive to?

All of these are important to determine a mutually beneficial destination. It’s not going to make you feel all romantic inside when you hit a ski lodge only to get out on the slopes and have your boyfriend finally tell you that he hates the cold.

It’ll make for quite an awkward predicament, so keep communication lines open and don’t rush the planning. It should be a fun experience, one that will see compromise and cater to both of your mutual interests.

Make sure you’re comfortable with him

If this is your first vacation together, chances are, the relationship is relatively new. This could mean that you still sneak out of his bed in the morning to touch on some makeup or brush your teeth, a la Annie in Bridesmaids—anything to give him the illusion that you most definitely woke up like this. Or, maybe, you’re still the sort of couple who doesn’t do gross things in front of each other, like a fart, burp or talk freely about poop.

Matters of the heart, truly

If that’s the case, you have to ask yourself: is staying in a room with him, with only one bathroom, going to be something I can handle, especially if I overloaded on the beans at lunch and really need to go Number 2? And oh, yeah, the bathroom has no fan?

Sounds like the plot of a horror film if you ask us, and Miranda from Sex and the City understood this predicament as she had to keep running down to the hotel lobby bathroom while on vacation with her new boyfriend.

This vacation together will either force you two to get more comfortable around each other, or it even may be something you might want to reconsider, especially if you’ve only been out with the guy a few times.

Dress appropriately and pack light to avoid looking too high-maintenance

Happy young couple trying to close suitcase at home

Yeah, yeah. We’ve all seen the jokes: a woman goes on vacation for two days, only to end up packing everything she owns, plus ten more bags. It’s a terrible stereotype; yet, it’s one that happens time and time again, leading men to try and avoid high-maintenance women.

Shatter the chances of him seeing you like this by packing light instead. If you’re only going on a weekend trip, chances are that you don’t need five bags of things. Same thing goes for a week-long vacation somewhere tropical. One large bag should do and you’ll probably find that you barely touched your bag at the end of the week, choosing instead to hang out in your bathing suit all day.

Over packing isn’t the only way that you can look high-maintenance. It also comes up when he wants to do something adventurous like go on a hike and all you want to do is sit by the pool, reading magazines and sipping on fruity cocktails.

And then, when you do finally give in to his hike idea, you show up in a skintight dress, face full of makeup and high wedges that make you whine and complain from the pain the entire time.

Not fun. Not for you and especially not for him, so make sure that you dress appropriately for every activity and compromise with him on some things. One day, you could do what interests you like partaking in a salsa lesson, followed by a lazy afternoon at the pool, while the next, you do something he likes, such as underwater snorkeling and a beautiful dinner on the water.

Leave the cellphone at home

If there ever were a time to not be on your phone 24/7, it’s most definitely during a vacation. After all, why shell out thousands if you’re not actually going to enjoy it?

But being on your phone on a vacation isn’t just about texting; it’s also about constantly taking pictures of everything. The palm trees, the sunset, that cute shirtless waiter that you hope your beau won’t mind you sneaking a photo of.

You may think that you’re doing something good for the long run, conserving those memories forever, but what about the memories in your mind? Wouldn’t it be more worthwhile to see the view from a helicopter ride in the mountains firsthand, with your own eyes, rather than through the lens of a crappy iPhone camera?

The memories you make are going to be the ones you remember. Not the fireworks show you just have to film, much to the dismay of your eye-rolling boyfriend.

And trust us, hardly anyone goes back years later to watch an old fireworks video. So, leave the phone in your hotel room, bring along one good camera and capture only the moments that are really worthwhile. You could even enlist the resort staff to capture some shots of the two of you—candid it usually best. Save the rest for your mind.

Get lost in all the romance

Young couple of travelers on a hill with stunning views of the ocean

Ever wonder how people on The Bachelor and The Bachelorette fall in love so easily? We are literally screaming at our TV’s (okay, maybe we’re a little drunk from too much wine) as we’re flabbergasted over how these men and women can so easily declare that they love another person after only 1 date and also adding in the fact that this person is also dating 24 other people.

It’s insane. But… is it? The Bachelor producers make up for that by kicking up the romance on the dates. A lot.

There’s helicopter rides, beautiful dinners that no one actually eats, private concerts for just the two of them, lots of champagne, flower petals upon flower petals… get the picture?

The contestants are quite literally smothered in romance, but this does the trick of giving them their dream dates and thus, making it so saying “I love you” to a complete stranger isn’t so crazy, after all.

So, follow suit on your vacation by indulging in all the romance. Get lost in it. Take hikes to beautiful places, go to dinners that will be filled with lots of wine and good conversation; sail around whatever ocean you’re at, make days be nothing about relaxation and fun.

Sure, you may feel cheesy at times, but, let’s be honest, a midnight bubble bath with some sort of jazz music playing in the background sounds a lot more romantic than just another night of Netflix & Chill.


About the author

Sarah Kester

Sarah is a writer, editor and aspiring author. Her writing has appeared in Elite Daily, YourTango, Fox News Magazine, The Richest, The Talko and Feather Magazine. She has a serious love for rom-coms, pink wine and "that's what she said" jokes.

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