Planning First Overnight Trip Together – 20 Handy Tips

Your first overnight trip together with your boyfriend or girlfriend could be a deal-maker or even a deal-breaker. Like you could discover endearing things about each other – how you love to sleep cuddling each other – you could also find your guy’s habit of overspending at the bar annoying or he could hate the way you sulk when the day trip has to be canceled because of the rains. 

While you embark on a journey of discovery on your first vacation (yes, we know you are jumping with joy because he asked you to go on your first weekend trip together) these are things you can’t avoid, but there are things you can.

Related Reading: Travel works for us as a couple by making us laugh at the most horribly wrong things

As a couple, you can make things work better if you plan well. Proper planning will go a long way in deciding how your vacation will shape up. 

Why you should travel with your partner? Travel is a great way to bond, understand each other better and it’s a great way to dig into your strengths and understand your weaknesses. We have some great first vacation with boyfriend ideas, just read on.

When your relationship is still nascent and you spend a few days together you get a better idea of how your partnership would turn out in the future.

One warning though, while traveling people are in a different mindset so don’t judge them at every opportunity over the smallest things. 

When Should You Take Your First Overnight Trip Together?

There’s no rule book on the exact time you should take your trip after you become a couple but common sense says that when your relationship has matured a bit and when you know each other better and are happy to share the bed and the bathroom without worrying about being judged, it’s the right time to take the trip.

Just don’t embark on your first overnight trip with your new boyfriend, you might be in for some nasty surprises. 

OnePoll conducted a survey of 2000 Americans who travelled together and they came to the conclusion that taking the first overnight trip together when your relationship is 10 months old is probably ideal.  

The survey also found out that 23% couples broke up after their first trip but 88% said their first vacation was a success, and 52% returned to the same destination sometime in life to re-live the first vacation. 

Most respondents said their first overnight trip together was a success because they picked the right destination (69%), having a budget that works for both partners (61%) and good planning (60%).

Making sure you and your partner are serious about each other (51%) and being able to compromise (44%) were also contributing factors. 

So now we will tell you your first vacation as a couple ideas. How you should plan it right. 

Planning First Overnight Trip Together- 20 Handy Tips

If you are looking for first vacation with boyfriend ideas then we must tell you that before you go on a holiday as a couple it’s important to keep a few things in mind to have a hitch-free vacay.

There are actually a lot of things to do on a vacation with your girlfriend but that depends on what you prefer to do as a couple and how much in tune you are about your vacation goals.

To be in tandem you just need to plan your first overnight trip together well. For that you need to communicate, divide responsibilities and do a few other things. Here are 20 tips. 

1. Decide on how you plan to use the smartphone

Before you decide on the things to do on a vacation with your boyfriend how you plan to use the smartphone on the vacation is the first step to having a great time together. 

Modern relationships are ruled by technology (now don’t tell us you were planning to carry the laptop or the tab on your first overnight trip together) and how your trip would fare depends on how you plan to use the smartphone. Have a talk on that. 

Ideally you should be switching off your phones and keeping it away. Leave your hotel room number with family and friends in case of an emergency. But if you can’t handle this intense smart phone detox then have stipulated checking times and try to avoid work calls.

The smartphone could turn out to be the most disturbing thing on your holiday so planning how you want to deal with it should be your first priority.

Related Reading: Technology And Relationships: Love Is Only Getting Better With Tech

2. Decide on the destination for your first overnight trip together

Planning First Overnight Trip Together
Planning First Overnight Trip Together

Once you have reached a consensus on the smartphone you need consensus on the destination. Your girlfriend might be a beach babe and you might love to watch the sun go down from the mountains, so what’s going to be your destination? What’s going to be your first weekend destination with your boyfriend?

This is the first step of understanding each other. You could go for a middle path decide on a place that’s got the beach and some rugged hills nearby too, or you could just want to do what works for your partner. 

Decide carefully so that you can look forward to the place you are going to. And most important, you should never feel that you compromised on your choices from the planning stage itself. This could throw you apart instead of bringing you together. 

3. Make it a short trip

If this is your first overnight trip together then it’s best to make it short and sweet. Make it over the weekend or if you want to throw in a day or two more do that. 

If you are looking for first vacation with girlfriend ideas we would say don’t go for elaborate travel either. Ensure you reach your destination quickly (by car, train or flight) and you have plenty of time for activities and relaxation. 

4. Work on a budget

Deciding on a budget is the most pertinent thing to do for any kind of trip. When you are planning your first overnight trip together and sit with a pen and paper to work on the budget, you will realize when it comes to the finances if both of you are on the same page.

You might want luxury all the way but your boyfriend could be someone happy with boutique and even budget hotels. Sit down and talk about what works for both of you.

A budget does not have to be a completely 50-50 scenario, one partner can chip in more but this should not be a topic of discussion when you are sipping wine in the hotel room.

5. Look for deals

That’s the best part of planning your first overnight trip together in advance. You get the best deals on hotel and flight bookings. You could get a five-star hotel for the cost of a three-star one if you keep scouring for deals. 

Then you could luxuriate happily without thinking that you are over shooting the budget.

An important tip for budgeting for your quick holiday is to keep a budget for daily expenses. Jot down what you plan to do and how much your daily costs would be. You are all set then. 

Related Reading: Rs 9000 For Bottled Water. No Way! Travel On A Budget

Enjoy planning the trip
Enjoy planning the trip

6. Enjoy planning your first overnight trip together

This is actually the most enjoyable stage when you are working on your first overnight trip together. The trip might last for four days, but you could savour the excitement of the impending trip if you start planning a few months in advance.

Talking about the trip and sitting with the travel planner is a heady feeling. You will find the thought of going away for the weekend with a guy could give you more happiness than a luxury spa visit. This is precisely the reason why you should travel with your partner. 

7. Divide responsibilities

Planning is fine, but the question is who is going to execute all the plans? Does your girlfriend expect you to do everything. Then you could be tired and resentful even before the flight has taken off. 

Divide responsibilities. While you could do the hotel booking she could do the flights. While you buy the backpacks she could get the medicine box in order. 

8. Insurance and medicines

Now that we have brought up the med box we will tell you that’s one of the most important things to carry on your first overnight trip together. Find out about each other’s allergies and emergency meds needed and pack it accordingly. Some countries don’t allow certain medicines to be carried so be careful about that.

And getting insurance that covers you for medical emergencies, theft, robbery, and other related situations will be prudent. Do a bit of research on what kind of insurance you want. 

9. Pack light for your first overnight trip together

You might be thinking, “It’s my first trip with my boyfriend what to pack?” We will tell you definitely don’t take 20 sets of clothing and five pairs of shoes.

We know women love to travel with their wardrobes but on your first overnight trip together please don’t shock your guy by turning up with three suitcases. 

Ideally, keep everything limited to one big backpack. Discover the virtues of traveling light. Focus on the essentials and pack intelligently.  

10. Focus on your strong points

While you are planning your first overnight trip together you will realize that one person is good at one thing and other is good at something else. So put your strong points together and function as a team. This will help you if you planning to choose your life partner on this trip.

If he is great with online bookings let him handle that if researching for the right insurance is your thing, you do that. You can decide on who would be behind the wheel when you hire a car and who would choose the restaurants on the way. Teamwork is your strength. 

11. Discuss what you would like to do together

Do you want your vacation to be filled with activities and explorations or you want to relax more and do less? 

Remember two people always approach a vacation differently and when it comes to a couple, usually one person is more enthusiastic than the other. There’s nothing wrong in that but once you discuss what you want to do on the vacation then you are clear in your head about what you will enjoy doing together. 

12. Plan the breaks

Why you should travel with your partner? Because you want to enjoy a break together. While that is true, we believe you also need to take breaks from each other. Being joined at the hip is definitely not healthy.  

Constantly spending time together could become too much. So while she takes a nap you could catch up on some football on TV. If you discuss this in advance, neither of you will feel ignored. You will realize that space is needed and you will be willing to give that. 

Related Reading: How To Tell Your Partner That You Need Space When You Are Upset

13. Be laidback

Going away for the weekend with a guy does not mean taking over his life. It could be cute to tell him to wear that Hawaiian shirt you gave him, to the beach but you can’t decide what he wears every time you go out together. Then don’t keep telling him to gel his hair because you like it, or finish the drinking session at the second peg. Heck! The poor guy’s on a vacation with his girl and not with his mother (even moms don’t do that, dear.) 

Guys also sometimes become nags and they become finicky about the swimsuit she’s putting on or the shorts that’s too short.

The idea is to be laidback and cool on your first overnight trip together. Let your partner be themselves. You will enjoy more.

Also, don’t let disappointments of inclement weather or cancelled plans get to you. Take it in your stride and just enjoy each other’s company.  

Enjoying each other's company
Enjoying each other’s company

14. Discuss expectations on your first overnight trip together

That’s another very important thing to talk about. If you like to explore a village would you like to do it alone and would you be cool with him sitting at a wine cellar and trying some new wines then?

Do you want your trip to be all activities or do you want it to be food, fun, and snooze? 

Talk about your expectations and be on the same page. Most couples end up in fights and misunderstandings on a holiday because their expectations from each other are very different.

15. Work out a schedule

If you could plan your days in advance then your first overnight trip together could be most fulfilling. You could be a late riser but your guy could be a 5-am person then when should the guide come to the hotel with the car? 

Decide on a time you are okay at going out in the mornings. Would you prefer to rest in the afternoons or would it be a good time meant for the pool?

 Having a schedule would mean you know when to wake up and what to expect when. 

16. Try new things

You never tried crabs because you were never sure how it would taste. But he loves crabs. Try it out with him.

You love jet skiing but he’s never tried it. Take him pillion and he would just love it. He wants a hotel with a swim-up bar because he loves his beer in the pool. Join him there and try this new experience.

Trying new things and discovering each other is the whole idea of going on your first overnight trip together. 

Related Reading: 51 Cozy Winter Date Ideas To Try This Year

17. You should be able to compromise

Traveling together does not mean you put your foot down when you want something. It’s about compromises and making space for things your partner loves to do. 

A bit of compromise is the only way to find bliss and you should do it lovingly. Do not try to show that you are making a huge sacrifice by not going to the beach when he is in the the mood for an afternoon nap.

Snuggle into bed with him and make the most of your time together. This small thing will go a long way in cementing your bond.

18. Be aware travel changes people

Be aware travel changes people
Travel could bring out the best

Your boyfriend could be an introvert and a bit of a workaholic as well. But when you go on a trip with him you could be surprised to see him talking nineteen to the dozen and never getting anywhere near work.

Travel changes people’s dispositions. It’s the whole idea of a new place, new ambiance and great company that people love. It brings out a different side to them. 

Sometimes the negatives come out too. So you have to be ready to deal with that. The usual ones are people get grumpy when the schedule goes for a toss, their anger issues might show up or they might become too lazy.  

19. Be ready for a bathroom situation

This is your first overnight trip together and this is the first time you are sharing the bathroom. He doesn’t know you take hours in there and neither do you know he makes 3-4 long trips in a day. 

So there will be a time when you will both need the bathroom. That’s when you will need to go back to point 17. Just a reminder: the hotel lobby has a bathroom, one of you can use for those emergencies. 

20. Plan to deal with arguments better

This is inevitable but whether you will let that escalate into fights also depends on how you mentally plan to deal with arguments.

Have a plan for dealing with arguments. You wouldn’t waste precious minutes of your vacation fighting then. 

As you have already realized meticulous planning could ensure that the moment you think about your first overnight trip together you would smile. A good way to let the wonderful feelings linger is to take out prints of the photos you clicked and create a wall with that. This would mean how much you valued the vacation and could pave the way for a fulfilling long-term relationship. Name the wall album, “Our first trip together.” 


1. Should I go on vacation with my boyfriend?

Yes you should. Going on a trip with your boyfriend or on a weekend getaway will help you to get to know each other better. You will also know if the relationship is meant for the long haul.

2. When should you take your first trip together?

OnePoll conducted a survey of 2000 Americans who travelled together and they came to the conclusion that taking the first overnight trip together when your relationship is 10 months old is probably ideal.

3. How soon is too soon to go away on a vacation together?

Maybe if you are only a couple of months into the relationship and getting a bit comfortable around each other, deciding to go on your first overnight trip could end in a disaster. Do it after around 10 months when your relationship is more stable.

4. What should I pack for my first trip with my boyfriend?

Definitely not 10 pieces of clothing and 5 pairs of shoes. Pack the basic minimum you need, carry insurance and emergency medicines and travel light.

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