The Ultimate Guide to Hooking Up On Vacation

Sun, fun — and much more. 

hooking up on vacation

(Last Updated on August 26, 2023 by Datezie Editors)

There’s a reason why so many songs are written about summer lovin’ and romances under the heat of the bright, beating sunshine. When we are free from the chaos of work, have more hours to enjoy daylight and have tropical getaways on our mind, our inhibitions are lower. This means putting your favourite hookup app aside, agreeing to a third (or fourth) cocktail,  immersing ourselves in a new culture, exploring exciting destinations — and perhaps meeting a temporary companion for the ride. (No pun intended.) 

If you’re heading out to take advantage of your paid time-off and you want to use the vacation days to explore your fantasies and enjoy the presence of someone as smokin’ as the triple-digit temperatures, consider this your ultimate guide to hooking up on vacation. By following these ‘do’s’ and steering clear of the ‘don’ts’, you set yourself up for a good time that doesn’t leave a — heart — burn.

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Do: Research your potential match online.

Even if your parents were able to navigate the tricky world of dating without the use of a smartphone, these days, everything you need to know about a potential match is available online. This can be a curse, sure, but also a blessing, since you want to ensure your safety in an unfamiliar place. As sexpert at, Coleen Singer explains, it’s worth the extra work to find out your hookup’s name and check ‘em out on Facebook, Instagram and other platforms. Not only will you find out about their personality, but you will save yourself from someone who has not-so-kind intentions or a history of being a stage 5 clinger. 

Don’t: Meet up at a hotel right away.

Breaking out of your comfort zone is part of the joy of traveling. Attempting to be more carefree than you are in your own zip code is also part of the fun of hooking up on vacation. But, there are some rules that always apply, no matter where your wanderlust — and well, your lust — tempts you. One of those non-negotiables according to Singer, is meeting at a public place. This — of course — is for your immediate safety when you’re navigating a new place, but also for your long-term reputation. As Singer explains, you never know if your fling has a hidden camera installed in his or her home, so a neutral ground is a better solution for your night (or nights) of lovemaking. She suggests booking your own hotel room or AirBNB to protect yourself.

Do: Pay extra to swipe in your vacation spot.

Who says your courting and flirting has to start once you touch down? If you ask online dating expert Julia Spira, researching for your hookup buddy can begin far before you pack your bags. For those who don’t need the spontaneous aspect of a casual encounter, she suggests paying extra to swipe and search in your upcoming destination, like Tinder’s Passport feature or Match’s upgraded option. “This way you can start chatting with someone in advance, let them know about your travel plans, and start flirting with the help of your mobile phone,” she continues. “I also recommend mentioning at the top of your profile that you’re planning vacationing in Miami and include the time you’ll be there. This lets someone know you’re just visiting…  and don’t reside there.”

Don’t: Only use apps.

You know what can go a long way in attracting someone who is up for a horizontal tango sesh? Smiling! Or saying ‘hi’ to a cute someone you see. Though current generations rely heavily on dating apps, Spira says living in the moment and really investing in the laid-back, carefree vacation state of mind will naturally make you more irresistible. Need some great ice breakers? Try asking where he or she is from, complimenting them or even asking for assistance getting from point A to point B. Kindness and a gregarious attitude can sometimes go further than a clever pun online or a suggestive photo.

Do: Set expectations ahead of time…

…not only for your hookup partner but for yourself. Especially if you’re more of a relationship type of person than a no-strings-attached shopper, it can be difficult to separate your feelings from your X-rated activity. As matchmaker Susan Trombetti explains, you shouldn’t treat it like a relationship when it’s clearly not going to be one — and if you can’t handle that, it is in your best interest to skip the sex. If you are okay with a temporary set-up, make sure to have a candid discussion ahead of time. Sometimes, a fling can turn into more, but it won’t if you don’t begin on the same page. “You can both state you will see where it goes later and you are open to it, or if this is just no more than a summer fling. It helps to know where you stand so you can have fun one way or the other,” she continues. “It isn’t weird to set the ground rules or discuss ahead of time. It also doesn’t take the excitement out of it. If you feel emotionally safe, it might enhance it.”

Don’t: Be stupid about your health.

Though what happens in Vegas stays in Vegas — any sexually-transmitted diseases contracted on vacation come with you. (Sorry, bro.) In matters where you probably won’t see this person again, you don’t want to have to worry about getting a bummer diagnosis or a potential unwanted pregnancy. Spira says protection is mandatory — as are conversations around health. You want to understand how active your partner is before making your choice to sleep with him or her, and make sure their on Team Condom. “Hooking up usually involves sexual activity, and whether you’re hooking up for one night, or desiring to meet someone for your entire vacation, you need to have the talk about safe sex and use protection,” she explains. 

And if you’re in a spot for a lengthy period of time? It’s also a good idea to have a conversation about who they will shag when they’re also spending time with you. “Even if you’re just having a summer hookup, you probably won’t want to be in rotation, or run into the person making out with someone else at the spot you met the night before,” she shares. “Many singles enjoy having casual sex with the same person, even if it’s a FWB or hookup situation.”

Do: Let loose.

Sure, before you visited Thailand, you had never drank beers from the back of a tuk-tuk. And before you traveled to Europe, you never witnessed a — legal! — peep show in real life. Being on vacation means that you’re trying new things that you typically wouldn’t do at home, and that’s a great formula for a romantic interlude, according to dating expert and host of The Manwhore Podcast, Billy Procida. Though you should still ensure your safety and check in with yourself that you’re comfortable, it’s important to break some rules and well, let loose already! “This is vacation — and vacation is that magical time when we leave towels on the floor, eat food we’re not ‘allowed’ to eat, and maybe do anal with a stranger,” he explains. “Normally have an age maximum for sex? Give that older lady a chance to communicate physically. Hate sleep-overs? That local knows a good brunch spot and those crepes may be worth one tipsy snuggle.” 

Don’t: Get clingy.

Repeat after Spira: hooking up on vacation doesn’t warrant the use of that scary three-word declaration while you’re savoring the post-coital glow. “There’s a difference between love and lust, and with a hookup, you might be tempted to say ‘I love you,’ when in fact you’re just feeling lusty and sexual,” she explains. Though it’s totally normal to instantly bond with your match after sex, it’s important to address if you’re really hoping for something more serious — or if you’re just overwhelmed by desire. If it’s the former, you should prepare for a letdown if they don’t return your more-than-intercourse affection. “If you start getting needy or clingy, it will appear that you’re not as easy going as you pretended to be, and your summer hookup may end abruptly,” she warns. 


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