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First Vacation With Boyfriend (27 Tips On How To Spend Your First Vacation With Him)

You’ve been seeing this guy for a while, and you have to say things have been going well between you. Your relationship is new and exciting, but beyond the fun you have, you’re starting to consider there might be something more meaningful budding.

Then one Friday evening, he’s at your place, both of you are chilling, and boom! He casually brings up something serious out of nowhere. “We should go on vacation together.” Maybe yours didn’t quite happen like that. Hell, it was probably even your idea or better yet, a joint one as a reward for working so hard.

How the idea came up matters little in this context; what does is that you’re going on your first vacation with your partner! I bet your initial reaction was excitement, but if you’re anything like me, you’ve probably also thought about a thousand and one ways things can go wrong.

We hear about vacation failures all the time. While it gives many couples interesting dinner stories, you’re not quite sure your relationship is mature enough to survive such mishaps yet. Well, how about you go through the following tips and see how you feel afterward?

27 Tips on How to Spend Your First Vacation With Your Partner

1. Consider if this is a good time for a trip together

Just because he’s asked doesn’t mean your relationship is ready for this step. Do you feel comfortable with each other yet? Do an honest assessment to see if spending that much time together would help improve things between you and not go the other way around. 

If it was his idea, it might help to ask the reason he has in mind. Does he just want you guys to relax, is it a random romantic gesture, or is his intended purpose getting you acquainted with his friends or family? Knowing this will help you determine whether or not you’re ready for the vacay.

2. Determine your and your partner’s idea of an ideal vacation

Now, what do you picture when you think of a holiday? Does it tally with what your man has in mind for this trip? Since this would be your first time together, I think it would be fair for everyone to be on the same page. 

You may be of the impression that you’d be going to a serene place where you can be one with nature. But if he’s more of a city and luxury kind of guy, one of you may end up disappointed.

3. Can you afford it? Can he?

The previous point will help you know how to budget. Once your destination and a rough idea of the kind of activities you hope to do is on lock, the next thing to naturally discuss is the cost. This part may be uncomfortable, especially if your relationship is still relatively new, but it’s better to hash it out before you go on the trip.

4. Find out for yourself with a short trial trip

Beyond the money part, which is one of the most common causes of couple fights, by the way, can you stand each other for a long time at a stretch? Arrange an exploratory trip, maybe a weekend away, for the two of you and see how that goes. If you end up fighting more than you bond, you might want to reconsider this trip.

5. Plan the main trip together

If you do make it past the mock-getaway, it’s time to start planning. Make sure to review each side’s opinions on the proposed destination, accommodation, and transport standard as well as the budget, and a rough idea of what you each want to do. While spontaneity is also a viable plan, it’s best not to leave too much to chance on your first getaway with a partner.

6. Choose a convenient locale

Before you decide on your destination, make sure it’s not somewhere too far or too stressful for this first time. If the place you’ve always wanted to visit with a partner will require two to three flights, you might want to save that for your next trip or the one after that. 

Go to a place where the fun can start right away rather than where you’d both need days to adjust to the living condition or tend to your health.

7. Get your mind in vacation mode

get your mind in vacation mode

As the date draws closer and you excitedly plan and make bookings, don’t forget to prepare your mind too. Get yourself mentally ready to travel and enjoy your stay there. Clear as much of the things that you know may continuously draw your consciousness back home as you can. We’ll talk about your expectations for the journey in a minute.

8. Give your body a treat

While you work on the mind, remember to extend the same courtesy to your body. Invest in a full baby girl treatment and let the relaxation start from home. Groom all that needs grooming, and do all you deem necessary to get that body ready. This will help you feel more confident and comfortable in your own skin, not to mention how much your beau would appreciate it.

9. Pack light

Even if you’re talented in the art of folding and arranging a heap of stuff to fit into a backpack, the more you load, the heavier it becomes. Depending on where you’re going, you may need to haul around your bags for hours at a stretch. Also, having too many loads means more things to keep an eye on. 

10. Keep your itinerary loose

Like I said, having a rough idea of what you would be doing is advisable. Yet, it is just as important to leave room for changing your mind if the need arises. You may get there and realize not everything is as advertised or that you enjoy some other things more. Keeping your schedule loose gives you more wiggle room even if you don’t end up needing it.

11. Make your expectations realistic

Your expectations for a trip can make or mar your overall experience. If you intend to have a tension-free vacation, try not to get your hopes up too much. 

Disappointments usually come up in ways that are out of your hands and can ruin the whole thing if you expect every single thing to be magical. Apply this mindset to everything from your journey to the sex, and you may just be pleasantly surprised.

12. Have a plan for if things go south

Don’t just level your hopes, you and your partner should actively anticipate setbacks and plan against them. How will you handle unexpected weather conditions? What happens if your flight gets canceled or you get robbed? What if the hotel somehow omits your reservation, etc. 

Preparing for setbacks like these beforehand reduces, to a large extent, how deeply it affects you and how fast you can fix it.

13. Allocate enough time for the purpose of your trip

Most holiday destinations are packed with various activities that you and your partner will most likely get immersed in. 

Notwithstanding, you two shouldn’t get so carried away with these things that you forget your reason for traveling in the first place. Whether that is to spend quality time together, reunite with old friends, or meet family members, keep that purpose at the top of your list.

14. Spend some time apart

spend some time apart

Traveling with your partner isn’t a mandate to spend every second of the trip together. Of course, you should spend most of the whole thing with him as it wouldn’t feel like much of a couple thing otherwise. 

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Nevertheless, consider giving each other space for a while to do some independent stuff. This ensures that no one gets choked up, and you actually enjoy the moments you have with one another.

15. Do things you each want to do

What makes for a fulfilling vacation is knowing you gotta make some unforgettable memories with the person you love and also crossed some things, if not all, off your bucket list. This is where all the planning ahead of the journey comes in. 

Your budget and schedule should include a number of your individual must-do activities so that even if you compromise on other things, those important ones happen.

16. Don’t let FOMO drive you

The fear of missing out is a real thing where you focus on what others may be doing that you’re missing out on. It is a form of social anxiety that sucks out the joy in what you’re actually doing and consumes you with what you aren’t. 

If you know you’re prone to this, make a list of the must-dos I mentioned that you can realistically achieve, and consciously try to enjoy the rest without pressure.

17. Make friends with other people

Whether individually or as a couple, try and mingle with other people over there. Make friends with other vacationers you find interesting as well as locals that you can communicate with. 

You may be positively surprised to learn of some fantastic spots your travel agents didn’t notice, not to mention a relationship that could bud from there. Just be careful not to let your guard down or trust too deeply in case they have ulterior motives.

18. Make a road trip out of it

If the season is right and you have ample time, you could trade in your flight tickets for a rental vehicle and make it a road trip! You can create a playlist, pack the car full of snacks, and drive off into the sunset. 

You’ll have stops, get to switch places if you both enjoy driving, and though you may be exhausted by the time you reach your destination, you’d have made memories en route. 

19. Keep an open mind

You’re more likely to enjoy your trip with an open mind than without, more so when you go with a guy. In addition to the fact that it keeps you flexible enough to want to try new things (which you may end up loving), it also enhances your problem-solving skills. 

Don’t limit your experience to what you’re familiar with only. Try local cuisines, experience their culture, have a taste of what they’re known for, and try to say yes more than no to your companion.

20. Go easy on the booze

What happens in ‘X’ may indeed stay there, but remember, this is your first vacation together. By all means, feel free to act like a Roman when in Rome. Still, keep your wits about you so you don’t overindulge and exceed your tolerance

This should also apply to food and other consumables. You don’t want your man tending to you when he’s supposed to be having fun now, do you?

21. Remain mindful of your budget

remain mindful of your budget

Amidst all the fun, remember that what isn’t prepaid will still come out of you or your man’s pockets. With this being your first trip together and all, he may choose to suffer in silence rather than curb your spending and make you uncomfortable. 

You know how sensitive money talks can be. To avoid putting him in this difficult position, try and hold some money on your own so you can splurge without weighing on your joint fund.

22. Keep sensitive topics at home

Hopefully, you’ll have plenty to talk about and learn about each other on this trip. While you should try and remain as natural as possible, you should also be mindful of the things you bring up and how you react. 

Avoid blowing things out of proportion, and any issue that may fester into resentment or potentially taint your experience shouldn’t come up. Or better yet, settle them before you travel.

23. Communicate when you’re uncomfortable and encourage your partner to do the same

Not everything he does will sit right with you and vice versa. Even if one stays long enough with an angel, faults are bound to come up. An excellent way to follow my previous point is to talk issues over rather than leave them to pile. 

Try to let things go as often as you can, so you don’t come off as a nag. But also encourage each other to communicate the ones that upset you despite your best efforts to stay positive.

24. Don’t let setbacks rain on your parade

When the mishaps we’ve been talking about eventually show up, remember you’ve prepared for them and see solving them as a bonding process. The challenges you encounter may not be the ones you planned for, but if neither of you gets overly worked up, chances are they won’t be beyond fixing. 

See them as an adventure within an adventure and set a reward as motivation for getting through them. 

25. Live in the moment and not on your phone

Between the many Insta-worthy backgrounds and the dreamy experience, you’ll likely have, the temptation to immortalize everything in pictures will be high. 

However, while it feels great to update your online followers that you’ve arrived, focusing too hard on that can make you miss out on the moment instead of living it. Social media aside, limit your gadget time generally, including checking up on home and work.

26. Take time to truly relax

Whatever your goals are for this trip, I imagine kicking back is on the list. Between the fun stuff, the challenges, and the calculations, be sure not to trade your rest for anything. Take a break from all the activities for a while and just laze about in your hotel room. You may or may not have so much time to sleep, but I’m sure you can come up with other ways to unwind.

27. Take in the sights and enjoy yourselves

Most importantly, have a swell time! Even if all goes well and you two make a habit of traveling together, there are so many places to explore worldwide that you may never return to this destination. So, take as much of it in as you can, so you can go back home fulfilled


When should your first trip with your boyfriend be?

Many people believe a couple can be ready for their first trip within three months of being together. On the other hand, some think it’s never too early to go on a romantic trip with your man. It’s all about how well you know him and how comfortable you are with each other.

Where should I go on vacation with my boyfriend?

You should consider the destination that means something to both of you. A place where you can both achieve the things you want to do without one person feeling left out. It helps to do the research together so you can compare and contrast.

Is it too soon to go on vacation together?

If you are seeing someone and asking if it’s too soon to go vacationing together, chances are that it is. While how long you’ve been going out doesn’t seem to matter to some people, you should wait to settle into the relationship if it bothers you.

How do couples survive their first vacation?

You shouldn’t make your initial trips as a couple on a whim as you have no prior knowledge of what the other person is like on them. But if you prepare properly and tackle challenges with open minds without losing focus of the getaway’s purpose, you should do fine.

What is the 3-month rule?

Three months is a modest period to be in a relationship with someone before going on a holiday with them. Since traveling together implies a commitment on a certain level, anything earlier may be too soon.

To Conclude

So, would you say you’re ready for this trip, or should I mind my business? Provided committing too early isn’t your issue, the tips above should cover all you need. Nevertheless, if you think I missed something or have further questions, let me know in the comment section and kindly share the article while you’re here.

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This tool can help by uncovering hidden social media and dating profiles, photos, criminal records, and much more, potentially putting your doubts to rest.


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