The Dos & Don’ts Of Traveling Together (Without Ruining Everything)


Your first vacation in a new relationship is a big deal. It means that this person likes you enough that they’re willing to throw down some serious cash (and use up their precious, limited vacation time) in order to spend time with you. And this is almost certainly because they’re (at least moderately) into you and your charming personality and general hotness and almost definitely not because this has been one long con to get you onto a cruise ship and then murder you far out to sea so they can steal that $807 in your bank account. Almost, definitely, probably not.

But with the excitement of getting to lounge on the beach together, comes some pressure. What if it’s terrible? What if you find out that they cut their toenails on airplanes or it comes up in casual conversation that they think John Mulaney is “just okay.” Or maybe they voted for the opposite political candidate as you or didn’t vote at all because “what’s the point.” Maybe every time they order a drink on vacation they sing the entire, “Do you like Pina Coladas and getting caught in the rain?” song.

Worse still, what if you’re the one doing terrible, unforgivable things to them? What if you’re the toenail clipping person?

Have no fear though, friends, passionate admirers, and bitter ex-lovers — we’re here to tell you the dos and don’ts of your first couple’s trip. Because with the right set up, planning, and basic human decency your trip can be as smooth as possible. Maybe even fun? Follow these simple guidelines and you will be well on your way to standing in an infinity pool with your girlfriend or boyfriend staring at the rainforest for as long as both shall live. Or at least until you get bored.

DO keep both of your budgets in mind when planning.

The Situation:

You’re very, very wealthy. Instead of pebbles in your driveway, you use diamonds. Instead of cat litter, you use diamonds. Instead of toothpaste you just grind diamonds onto your teeth, every night, until they’ve been grated away to dust, painfully, one. by. one. But no big deal because you can replace them with DIAMONDS.

Naturally, you’ll just pick a hotel at random from a list a friend gave you. You’re not going to give that friend’s name but it rhymes with Bark Buckerberg (coincidentally that’s also the name of a dog you have an ongoing feud with. He knows what he did).

Why you should be looking up sales or try a hotel app:

Unless you’re paying for everything as a gift, your first trip’s opulence level should be based on the financial situation of the partner who has less money. Because — spoiler alert: You’ll both have more fun if one of you isn’t worrying that this trip is going to keep them from paying rent on time or drain the money they were saving for their cat’s diabetes medication.

“No, no, it’s fine. I love 90 dollar steaks and besides, Fluffy has lived a very long and fulfilling life, I guess (strangled sob). Yep. Let’s get in the hot tub. That sounds like a good place to cry. I mean kiss.”

Look, at the beginning of any relationship, you’re trying really hard to go with the flow and be easy-going. It means that it’s much harder for your bf/gf to say no to that nice hotel you swear has the softest pillows in the world or say, “are you f-ing kidding me. You know my cat has diabetes.” when you suggest a $300 pre-fixe menu. So do your partner a favor and pick a spot that will make everyone feel comfortable and not stressed.

(Although, if you’re both rich af, do whatever you want! And also, I don’t know, adopt me? Adopting adult women is a thing you can do right? Be my new parents, please? I’m nice!)

DON’T make a first trip that’s over two weeks long.

The Situation:

You look into bae’s eyes and see your whole life of adventure spread out in front of you as endlessly as the stars in the sky. What’re six months backpacking around South America compared to forever in each other’s arms? Tis a blip in the history of time. You know what they say: “When you meet the person you want to spend the rest of your life with, you want the rest of your life to start in a hostel in Columbia arguing about which one of you was responsible for leaving your passports on a bus.”

Why you should make it more of a quick “Tuesday Siesta” than a “100 Years of (Non) Solitude” situation:

Sure, long bouts of travel might be incredible with this person. Maybe. But if it doesn’t work out? Ooooo boy. You’re now stuck with a nightmare companion who only wants to watch Mad Men on his laptop all day in bed and hates “weird food.” And if you’re in it for the long haul, you’ll start wishing every single train you take to a new country would just lose control and go off the rails but without Liam Neeson there to keep you all from going to your fiery death.

For the first trip, just keep it on the shorter end. Dip your toe into the waters to see if you’re going to be in the company of a sweet, sweet manatee who just wants a hug or a literal shark who will bite off that toe and still be hungry for more of your flesh.

DO pick somewhere neither of you know well.

The Situation:

What’s that you say? My new lover has never been to Paris? Never? Why I’ve never heard of such a thing. Not even in college? Well, that won’t do. I’ve been to Paris hundreds of times. Thousands. Millions. He has to go to Paris! We have to go to Paris! EVERYBODY NEEDS TO SEE PARIS.

Why you should close your eyes and stop a globe with your finger:

You might have the impulse to take your boyfriend/girlfriend/partner somewhere you know well in which you can wildly impress them by showing them the world, shining shimmering splendid. And that worldliness will be great on a future trip, I promise. But for the first trip, it’s best to make new memories and be on equal footing.

You don’t know each other that well. So even though you think you know the best restaurant that they’ll “totally love” maybe they won’t. And they’re worried now about hurting your feelings. Or you have to feel stupid that you picked Crabby Chris’s Crab Emporium when it’s not as good as you remember, and also, put your new lover into anaphylactic shock.

Going to a place neither of you has been (or at least knows well) will allow you to explore together, create new memories, and both feel empowered to make suggestions because you’ll both feel ownership over your first trip together. (And for the love of God, do not plan your first vacation in a spot where you and your ex had a romantic time once.)

DON’T leave without figuring out the money stuff first.

The Situation:

Isn’t it kind of awkward to talk about money and not very sexy? You’ll just feel it out when you get there. You’re pretty good at home taking turns with treating or splitting the check! Never look before you leap, your grandmother used to say. Boy, do you miss her since her shocking fall to her death. Who saw that coming?

Why you should learn how to make a quick spreadsheet:

In a situation where you’re dropping a lot of dough and you’re eating EVERY meal together, the financial stuff isn’t just something you forget about easily. It gets brought to the surface over and over again. And you really don’t want to be constantly calculating who paid for what and harboring secret resentments every time the bill arrives. Before your trip, know each other’s budgets. Discuss what you’re comfortable splurging on or not. Then figure out if you want to pool cash and use it for meals and activities or put it all on one credit card and split it later.

Be sure to schedule in some room to be generous, too. Sure, you paid for the surf session and she paid for a slightly cheaper dinner. But if part of you is truly fuming that you ended up paying 50 bucks more on a vacation, there might be a bigger problem in your relationship. I’m no therapist (I’m just an omniscient advice God who is always right) but, most likely, finances are already something you’re frustrated about in everyday life. So you should try to work that out before you head to Tahiti and lose it when she doesn’t reach for her credit card to pay for half of the vanilla ice cream you two plan to lick off of one another.

DO use your own suitcase.

The Situation:

You’re packing light, you’ll share a suitcase! Doesn’t that make you seem easygoing? You could wear literally one outfit the entire time or no outfit at all. You could fashion a suit from the hotel toilet paper. YOU’RE SO LOW MAINTENANCE!!

And besides, isn’t it sexy to think about your undergarments brushing up against each other?

Why you should keep some personal space:

Question: Does the idea of your undergarments all mixed in together sound as sexy when they’re dirty?

I’m all for getting comfortable, but it’s your first trip. If it’s adventurous and you want to pack light, better to both bring your own backpacks than share one rolling bag. You probably have different packing techniques and different ideas of what is essential and it’s a fight you don’t need to have before you even leave. It’s way easier to have your own little bit of personal space than dealing with the bag politics of who gets more space for shoes or all of those ceramic elephants filled with heroin that a nice man asked you to smuggle across the border.

DON’T be afraid to ask strangers to take your photo.

The Situation:

It would be rude to ask someone else to take your picture even though you just did a once in a lifetime climb to the top of Mt. Everest. What if they say no? Or worse, look slightly annoyed. What if they sigh, and say, sure. But in a way that makes it clear they don’t want to. Nah, better not to risk it. Better to just snap a couple of selfies. No biggie. You climb Everest all the time.

Why you should make some strangers to be your Instagram boyfriend:

Selfies can be fine, but they’re generally not something you want to frame and hang in your living room. You just went on this awesome trip — you should get a couple of nice pictures of the two of you together, in front of pretty backdrops.

Rules of polite society apply on this — ask someone lingering. Don’t ask someone clearly hurrying somewhere, or wearing headphones, or reading. The best way to get someone to take your pic painlessly is to look for a couple taking single pictures of each other or one person being left out of a group shot and ask them if they’d like you to take it so they can be in it. 99.9 percent of the time, they really appreciate it. And will be happy to return the favor quickly. Make the effort, you’ll be glad to look back at it when you’re old and grey and married to totally different people (statistically speaking).

DO poop in the hotel room.

The Situation:

You live in separate places! Normally, you just have a fun night. Then you make an excuse when you need to go to the bathroom and go back home for a nice leisurely poop with no one you have romantic feelings for outside the door listening to the horrible, horrible sounds coming out of your delicate body.

Why you should consider going for your “number 2” option on this one:

If we had our way, our significant others would never know that we poop. They’d never hear it or smell it or think of it. You’d pay to have the guys from Eternal Sunshine come over and wipe their memory of what transpired in the bathroom from their minds every night while they slept.

I’m sorry though, you have to break the seal on this one. Everybody poops and, on a trip, it will become uncomfortable to either hold it or run to the lobby bathroom over and over. It’s a lot of pressure, I’ve been there. A trip is the perfect time to finally admit you’re human.

That said, the most discreet way of doing so is taking a shower, starting the water to minimize sound, do your business and then jump in. You’ll get a little more time for any odors to evaporate and the smell of products you showered with will help too. Oh, and don’t go with the door open. Not ever. Not even after 50 years of marriage. It’s not okay. Some things we don’t need to share.

DON’T plan on having stimulating conversation the entire time.

The Situation:

God, you love talking to your partner. They’re so smart and funny and some nights, after a date, you just stay up for hours, talking. You usually end up accidentally closing restaurants down because you just lose track of the time. This trip is going to be a dream come true, you have all the time in the world!

Why you should have some Dan Savage queued up for the road:

If you’ve mostly only seen each other for a few dates a week, you might be expecting sparkling convo all the time. But traveling can be exhausting. And that’s okay. Seriously, it does not mean you are doomed as a couple because you realize here and there that you’ve run out of things to say. Be prepared with a mystery podcast you can start together or save up a few episodes of that comedy thing you both love. You will almost inevitably hit a point where you need to just not talk to anyone. Having some options that allow you to be together, experiencing something chill (without needing to come up with 20 questions about their high school mascot) is sometimes just what you need in order to recharge.

DO take a little time apart.

The Situation:

Wait. You’re on a trip together. You’re supposed to spend every second together, right? You guys were told first couple’s trip was the one in which a mad scientist was supposed to “human centipede” you, right? RIGHT????

Why you should keep the key to your room’s secret escape hatch:

Absence makes the heart grow fonder. It’s okay if one of you wants to read a book by the pool one afternoon and the other wants to go on a hike or hit up a museum. Sometimes you need a few minutes to just be weird, weird you. So run down to get a coffee in the morning and linger a little on the walk back. Be chill about just wanting different things a couple of times, and enjoy the peace that sometimes comes from not having the person you love most in the world reading you 700 menus of restaurants even though you told them you were fine with them picking.

Give yourself a break, you know? Otherwise, too much togetherness can lead to being a little stir-crazy and fighting.

DON’T plan so many activities that you’re too tired for vacation sex.

The Situation:

This is your first vacation together! You should do everything there is to offer! Scuba diving at 6am, rock climbing at 2pm, an amazing cocktail bar before that restaurant everyone talks about, a late night ghost tour at 10! AND THEN YOU’LL START AGAIN.

Fun! This is fun! They call this FUN.

Why you should make good use of your hotel room:

Vacation sex is objectively the best kind of sex. It just is. You don’t have to be up for work, you don’t have to be quiet for any neighbors (I mean you’re never going to see these people again and besides they are also having hotel sex), all of your stuff is in the same place, you’re more relaxed with lower inhibitions, and finally, if there are two beds in the room, guess who has a separate “sex bed” from the ‘sleeping bed’. YOU GUYS DO. Dream.

There’s certainly nothing wrong with not having sex on your vacation if you don’t want to, but, usually on your first romantic getaway, that’s something you’re kind of into. So… don’t plan things to death. Leave lots of room in your schedule for “naps” and “getting ready for dinner” and “having sex all day.” Give yourself the option for when the mood strikes.

DO pick an activity that takes you both out of your comfort zones.

The Situation:

Oh, you’re not going to do ANYTHING weird that will embarrass you in front of your new love. I mean, what if you look like a fool? You’ll stick to pointing out all of the kinds of birds you know on gently inclined walks, thank you very much.

Why you should totally leap out of a plane:

Doing things that scare you a little or get your heart rate up bonds you together. Adventure makes you feel connected and makes you more sexually attracted to your partner. Seriously, get that dose of heart-pumping adrenaline going through your body while looking into each other’s eyes and you’re likely to feel a higher sense of arousal later.

Plus, doing things that you aren’t good at or trying things for the first time leads to fun. You’ll laugh, you’ll mess up, you’ll learn something and that’s good on a first trip. It’s a better story to talk about the time you took surfing lessons, fell off your board, and were stung by a passing sting ray, than that time you both played a perfectly adequate round of mini-golf. So take one for the team. There might even be great “you were so brave” vacation sex after.

DON’T feel bad about re-examining your relationship if your partner is a monster to travel with.

The Situation:

Your awesome boyfriend who volunteers at charity programs for kids, and makes you extravagant dinners just because you had a hard day at work, and is so good at karaoke — has transformed into a literal demon from Hell who yells at waiters and hates the smell of the ocean for some reason, and whose eyes turn red every time you put your own music on and his head spins around and he vomits green bile into your face.

Why you should maybe hop back on Tinder for a bit:

When something is stressful like your partner’s bag gets lost, do they scream at everyone including you and are totally miserable to be around? Do they then not bounce back and spend the next 24 hours complaining about the pants in that bag and how they wanted to wear them tonight. Look: Of course travel stuff can be really stressful, we’ve all had our brief meltdowns but if your partner is terrible to be around through those stresses, consistently, I have news for you, they may not be great just…in life. Because you know what else is stressful: getting married, losing a job, having kids, your computer breaking, getting sick, getting a parking ticket, balancing your bank account, spending time with in-laws, learning a movie you wanted to see is sold out, finding out that the person who you thought loved you watched The Good Place without you…

Stressful shit will always happen. And the thing about traveling together is that for the first time you are spending every second with someone. So, if they’ve been The Picture Of Dorian Grey-ing you, and beneath the facade, they’re a super ugly human being, it’s a sign that this might not be “the one.” Look, I’m not saying you should immediately break up, but I’d give it a solid consider.

On a related note: Make sure you are not the monster that someone wants to break up with after the vacation. Go with the flow, compromise, find the fun in things, listen to what they want, don’t poop with the door open, be nice to service people even if every flight was canceled and they tell you it’s so that all of the pilots at LAX can eat a burrito at the same time for National “Pilots Eat A Burrito Day…”

“That cannot possibly be a real day,” you say. “Please stop lying to my fucking face. I just want to get out of this godforsaken — (Deep breath) I mean… when is the next flight you can get us on? I really appreciate you helping us here. We’re so excited to be on this trip.”

Our best advice, be the traveling partner you wish to be with. And you’ll find the right match. Maybe even on this very trip.