How to Ensure Your First Vacation as a Couple Isn’t an Unmitigated Disaster

Your first trip together is an important relationship milestone. Here's what you should know before booking any flights.

June 25, 2021 8:29 am
A man and woman on the beach
There are some things you should know before committing to a getaway with someone new.
Matteo Colombo

A few weeks ago I agreed to go on a weeklong vacation with a man I’d only been on one date with. I’m not exactly a stranger to this kind of impulsivity, though even I had my reservations. After careful consideration, however, I arrived at the conclusion that, ”Eh, it’s probably fine.” This is an assumption that has generally proven true of comparably questionable choices I’ve made in life, and once you’ve been out with enough strange men from the internet, you inevitably get kind of desensitized to potential threats to your own safety. After all, if you’re a woman who dates men, you’re basically putting your life in their hands every time you choose to go out with one, regardless of whether you’re jet-setting or Netflixing. If anything, the financial investment a vacation requires seems to provide some level of security; if a strange man from the internet wants to kill you, he doesn’t have to buy a plane ticket to do it.

The constant threat of intimate partner violence with which all women must contend on a daily basis aside, a first trip together as a couple is a major relationship milestone, whether it happens on your second date or your honeymoon. It’s an important opportunity to learn more about your partner, yourself and who the two of you are together  — including, possibly, some things you might not want to know. 

“It’s definitely an important relationship milestone,” says Courtney Kocak, co-founder and co-host of Private Parts Unknown, a podcast exploring love and sexuality around the world. “And depending on the trip, it can be a relationship test, as well.”

In order to help first-time traveling couples ace that test, or at least prepare for it, we tapped Kocak and her fellow relationship and travel experts to answer the most pressing questions all newly partnered travelers have, but may be too afraid to ask. 

How soon is too soon to go on vacation with a new partner?

Fortunately, Kocak says she isn’t aware of any rules dictating how long a couple should be dating before traveling together, though she does add that she “would be a little suspicious if a brand new partner wanted to go on a lavish vacation right away.” Oops. 

Fellow Private Parts co-host Sofiya Alexandra recommends spending at least a few weekends together before committing to a vacation. “The several-hour version of someone isn’t the several-day version of someone,” she tells InsideHook. “When you travel, unexpected things come up — from getting seasick to losing your luggage to being delayed at the airport. Those little inconveniences can reveal a different side to a person.” While few of us are at our best while dealing with airport headaches, “You don’t want to find out that your partner is unreliable or mean under stress in an unfamiliar location you may not be able to leave,” she adds, pointing to any Married at First Sight honeymoon episode for reference.

That said, Kocak adds that under the right circumstances, an early-relationship trip can be a great way to get to know each other better, and (hopefully) grow as a couple. Remember, there are no hard and fast rules when it comes to a relationship timeline; every couple progresses at their own pace. As long as you “feel comfortable spending 24/7 time with your new partner,” says Kocak, “you’re ready to travel together.”

So you’re going on vacation together. Where should you go, and for how long?

Again, most people would probably argue that it’s best to start slow. Kocak recommends a day trip to a nearby beach town to “test the waters, pun intended,” followed by a short getaway of one to two nights, max: “A quick weekend jaunt that only requires a few hours of travel is the perfect starter trip.”

Provided you’ve already spent at least a weekend or two together, Alexandra also suggests extending those two nights into a slightly longer getaway: “I’d say a long weekend is ideal, like four days around 4th of July or something like that.” Bonus points for somewhere neither of you has ever been before. “A destination both of you have had your eye on but never checked out is ideal,” she says, citing scientific studies that suggest “experiencing new things together as a couple keeps you in love longer than doing things you’ve done together before.”

For those of us ready to jump into the deep end, a four-to-five night stay is ideal, according to Pepe Aguirre, co-founder and CEO of Luxury Lifestyle Vacations, a five-plus-star travel brand curating fantasy-like travel experiences, workshops and cruises for sophisticated, sex-positive travelers. For a first trip together, he suggests sticking to the classic: “A resort on the beach with warm weather.” After all, he adds, “Less clothing required, you feel more free.” A resort can also take the pressure off of planning activities and dining, “so you really can be relaxed and enjoy those days.”

How should couples prepare for a first trip together?

“Both partners need to be on the same page,” says Claudia Aguirre, fellow LLV co-founder and vice president. “There are a lot of things that can go wrong if you haven’t taken time to discuss each and every aspect [of the trip] with your partner.”

This includes making sure you’re on the same page about what you want from the experience, which can mean surprisingly different things for two people en route to the same destination. “It’s crucial to figure out what kind of trip each of you wants to have before you buy your tickets and make your reservations,” says Alexandra. “If for one of you Hawaii is swimming with manta rays, snorkeling and hiking, and for the other Hawaii’s drinking lilikoi mai tais by the pool and reading, I’m sorry to tell you that you’re not gonna have fun in Hawaii.”

Claudia recommends setting some ground rules beforehand to ensure your expectations line up. That said, just because you’ve established a plan doesn’t mean you can’t veer from it. Staying flexible is key to enjoying a vacation for what it should be: a break from the obligations and rigid schedules of everyday life. 

“Make a pact with yourselves that vacation is exactly what it sounds like, a break from the pressures of regular life, so do not feel obligated to do anything that makes that ‘break’ feeling go away,” says Alexandra. “If at night you made a pact to hike early morning, but when the alarm rings, neither of you want to? Turn that bad boy off, curl up together, sleep in, and then order room service. BOOM, what pressure?”

What anxieties might new couples face on a first trip together, and how should they deal?

Yes, I’m talking about pooping, but also not pooping — and also not not pooping. Besides the inevitability of normal bodily functions, there are a slew of existential woes that might creep into your mind after you’ve packed your bag and checked into your flight. After all, another person is going to have 24/7 access to who you really are, usually when no one else is looking.

“Some concerns you might have about traveling with a new partner — your safety, for example — are totally legit, and you should do a proper risk assessment and keep your eyes open on that front,” says Kocak. “But don’t waste your time worrying about doing something embarrassing around your new partner. If you fart in the car, who cares? Your new boo better good-naturedly roll down the window and laugh it off, or they’re not really worth being boos with in the first place. That’s how traveling together can be a great compatibility test.”

“You might worry about your partner seeing you in a less flattering light for whatever reason — like the version of you they’ve really liked so far might disintegrate if you let them in further,” says Alexandra. “For some it may mean having their partner see them without makeup consistently, or find out they’re afraid of the ocean, or even simpler stuff like getting diarrhea from a new food.” For these woes, “Take a deep breath and remember — if someone doesn’t want to be with you because you got diarrhea and can’t swim, you definitely don’t want to be with them.”

While it may be tempting to add some buffer against potential humiliation and/or awkward silences by traveling with friends, Kocak cautions against adding others to the mix. “Be careful about inviting extra people. If you’re trying to connect with your new lover, they might get in the way,” she warns. “Plus, the more personalities and opinions involved, the less control you have over your itinerary. And definitely steer clear of a meet-the-family style trip on your first adventure out of town together.”

In conclusion: if you can’t stand the thought of an extended length of uninterrupted time together, you probably shouldn’t be traveling together. Also if you have to take a shit, just take a shit.

What about vacation sex?

For the vast majority of allosexual couples, going on vacation together carries the implicit promise of prolific vacation sex. But like other sexual encounters whose reputation precedes them — wedding night sex, prom sex, first-time sex, etc. — the pressure to have frequent, passionate vacation sex can be daunting, and ultimately set one up for disappointment. As Alexandra puts it, “Anytime pressure enters the building, everything else leaves, so just keep that in mind.” 

In other words, “Vacation sex is awesome, but the pressure to have mind-blowing vacation sex is not. So don’t stress about the outcome,” says Kocak. “Set the intention that you just want to have fun with your partner and let the rest flow from there. Having fun is natural lube for spontaneous sex.” 

“Act when the moment moves you — that’s the beautiful thing about being outside of the rules of time and responsibilities on vacation,” says Alexandra. After all, she adds, “You’ll feel a lot hornier when your shoulders untense, promise.”


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