Planning First Overnight Trip Together – 20 Handy Tips

Love and Romance | | , Writer
Updated On: September 6, 2023
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Your first overnight trip together could be a deal-maker or even a deal-breaker. You could discover endearing things about each other – how you both love cuddling or how your partner overspends at the bar. And they could also get to see your grumpy side and you theirs, especially when things don’t go as per your plan. 

As you prepare to embark on your first vacation, we are here to help you with some handy tips. You can make your first trip together as a couple a memorable one with some planning and preparation. So, let’s cover all the bases to make sure that the decision to go away for the weekend or even an overnight staycation brings you closer and cements your bond.

When Should You Take Your First Overnight Trip Together?

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Before we get to the timeline of taking a trip as a couple, let’s address another important question: why should you travel with your partner? Travel is a great way to bond, and understand each other better and it’s a great way to dig into your strengths and embrace your weaknesses. 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 become different versions of themselves. So don’t judge them over the smallest things. 

There’s no rule book on when exactly you should take your first trip as a couple. But common sense says it is when your relationship has matured a bit, you know each other better, and are comfortable sharing the bed/bathroom. Perhaps, after you’ve spent a few nights at each other’s place would be a good time to start discussing a trip.

OnePoll conducted a survey of 2,000 Americans who traveled with their partners and concluded that taking the first couple’s vacation when your relationship is 10 months old is probably ideal. The survey also found out that 23% of 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 relive the first vacation. 

Most respondents said their first romantic vacation was a success because they picked the right vacation spots for couples (69%) and planned a budget that worked for both partners (61%)

Making sure you and your partner are serious about each other (51%) and being able to compromise (44%) were also contributing factors. Now that we’ve broadly covered the factors that go into pulling off a successful first trip as a couple, let’s get into the details of how you should plan your first night away with your partner.

Planning First Overnight Trip Together – 20 Handy Tips

According to studies, travel helps increase communication, reduces the possibility of divorce, strengthens lifelong bonds, and contributes to a sense of well-being. So, travel as much as you can. But do it right…

If you are planning your first vacation as a couple, it’s important to keep a few things in mind to have a hitch-free vacay. Everything entirely depends on what you prefer to do as a couple and how much in tune you are with your vacation goals. And for that, you need to communicate, divide responsibilities, and so on. Here are 20 tips that will make your couple trip LIT AF:

1. Decide on how you plan to use the smartphone

How you plan to use the smartphone on the vacation is the first step to having a great time together. Sometimes, social media and relationships don’t go well together (now don’t tell us you were planning to carry the laptop/tab on your first trip together!) So, discuss smartphone use beforehand.

Ideally, you should switch off your gadgets and keep them away. Leave your hotel room number with family and friends in case of an emergency. But if you can’t handle this intense smartphone detox, then have stipulated time for phone use and try to avoid work calls.

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

2. Decide on the destination for your couple trip

You need a consensus on the destination

Once you have reached a consensus on smartphone use, you need a consensus on the destination. What if your partner is a beach person and you love the serenity of the mountains? So, what’s going to be your destination? What’s going to be your first weekend destination with your boyfriend/girlfriend?

When your ideas of an ideal holiday are polar opposites, your compatibility is put to test. The best way out of this conundrum is to find a middle path. Perhaps, decide on a place that’s got a beach and some rugged hills nearby too. Or you could go with your partner’s choice of destination for this trip and yours for the next, or vice versa.

3. Make it a short trip

Since it’s your first time taking an overnight trip together, it’s best to make it short and sweet. Plan it over the weekend. If you want to throw in a day or two more, do that. Avoid being too elaborate on your first vacation with your girlfriend/boyfriend. Ensure that you reach your destination quickly (by car, train, or flight) and have plenty of time for activities and relaxation. 

4. Work out a budget

Deciding on a budget is the most pertinent thing for any kind of trip. When you are planning your first overnight trip together, sit down and work out a budget. It’s important that you both are on the same page regarding the finances.

You might want luxury all the way but your partner could be happy with a boutique hotel and even budget BnBs. So, it’s imperative to discuss 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 online and offline

That’s the best part about planning your couple’s travel 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 if you keep scouring for deals. Then you could luxuriate happily without thinking that you are overshooting the budget.

It’s your first time spending the weekend together; you can’t miss out on great date ideas to make it more memorable. 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. 

6. Enjoy planning your romantic escape

Planning your romantic escape

This is the most enjoyable stage when you are working on your couple’s trip. The trip might last for four days, but you could savor the excitement of the impending trip if you start planning a few weeks in advance. Talking about the trip and sitting with the travel planner is a heady feeling. The thought of going away for the weekend with your loved one could give you more happiness than a luxury spa visit. This is precisely why you should consider traveling with your partner often.

Related Reading: Sharing Expenses In A Relationship – 9 Things To Consider

7. Divide responsibilities

Who is going to execute all the plans? If your partner expects you to do everything, it could make you tired and resentful even before you’ve arrived at your destination. Divide responsibilities. While you could do the hotel booking, they could book the flights. While you buy the backpacks, they could get the medicine box in order. Allocation of tasks is one of the tips for planning an exotic couple’s trip.

8. Insurance and medicines

What would be a handy tip that makes travel for couples easier? Make a list of medicines you and your partner tend to need often and pack them. And getting insurance that covers you for medical emergencies, theft, robbery, and other related situations would be prudent. Research a little on what kind of insurance you want. 

9. Pack light for your couple vacation

Packing for your first weekend together can be challenging – women, we’re looking at you. We get that you want to knock your partner’s socks off, take their breath away, leave them gushing, and all that. But don’t overboard and end up with 20 sets of clothing and five pairs of shoes.

We know you love to travel with your wardrobes but on your romantic getaway, please don’t shock your partner by turning up with three suitcases. Ideally, limit your baggage to one big backpack. Discover the virtues of traveling light. Focus on the essentials. Yes, your partner wants to go away for the weekend. But no, they don’t want that whole weekend to be about helping you choose what to wear.

10. Focus on your strong points

While you are planning your couple’s vacation, you will realize that you each have your own strengths when it comes to planning and executing your plan. So put your strong points to good use and function as a team. The answer to how to choose a life partner lies in finding someone who can complement your strength and weakness, and there is no reason why your first trip together can’t be a step in that direction.

If they are great with online bookings and researching the right insurance is your thing, then divide the tasks accordingly. You can decide who would be behind the wheel when you hire a car and who would choose the restaurants on the way. With teamwork, you can make it your best vacation yet.  

11. Discuss what you would like to do together

Do you want your vacation to be filled with activities and explorations or do 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. So, discuss what you both expect out of this vacation. More hustle or chill vibes?

12. Plan the breaks

Why should you travel with your partner? Because you want to enjoy some downtime together. While that is true, we believe you also need to take breaks from each other. Being joined at the hip is not healthy. Constantly spending time together could become too much. So while your partner 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 necessary even on a romantic vacation and you will be thankful for it. 

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 partner does not mean taking over their life. It could be cute to tell them to wear that Hawaiian shirt you gave them, but you can’t decide what they wear every time you go out together. Don’t keep telling them to gel their hair because you like it or stop after two drinks. Heck! They are on a vacation with you and not with their parents. A controlling relationship is the last thing anyone wants.

Do nag or be too finicky. Just try and go with the flow to make the most of this vacation. Decided on places to go with your partner but couldn’t make it happen? Don’t let disappointments of inclement weather or canceled plans get to you. Take it in your stride and just enjoy each other’s company.  

14. Discuss expectations on your first overnight trip together

Research points out that couples with greater travel experience plan every little detail beforehand to avoid conflicts on the trip. For instance, if you want to explore a quaint village en route, would you like to do it alone and would you be cool with them sitting in a wine cellar and trying some new wines? Talk about your expectations so that you are on the same page about your bucket list. Most couples end up fighting on a holiday because their expectations of each other are very different.

15. Work out a schedule

If you could plan your days in advance, then your couple’s getaway would be the most fulfilling. You could be a late riser and your partner a morning person. So how will you plan your activities? Yes, you guessed it – by finding a middle path. Would you prefer to rest in the afternoons or would that time be better spent at the pool? Having a schedule means giving your holiday some structure and avoiding last-minute conflicts and disappointments. 

16. Try new things

You’ve never tried crabs because you were never sure of how they would taste. But they love crabs. Why not try it out with them? You love jet skiing but they have never tried it. Take them pillion and your partner would just love it. They want a hotel with a swim-up bar because they love having a beer in the pool. Join them there and try this new experience. Trying new things and discovering each other is the whole point of a romantic vacation. 

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 sacrificing in a relationship by not going to the beach when your partner is in the mood for an afternoon nap. Snuggle into bed with them 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

Travel could bring out the best

You could be dating an introvert and a workaholic. But when you go on a trip with them, you could be surprised to see them 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, a new ambiance, and great company that people love. It brings out a different side to them. 

Sometimes it can bring out the negatives too. So you have to be ready to deal with that. The usual ones are people get grumpy when their 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 couples getaway and it’s likely going to be the first time you are sharing the bathroom. Perhaps, your partner doesn’t know you spend an hour in the shower and neither do you know they make 3-4 long trips to the loo in a day. So there may come 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 depends on how you navigate the situation. Have a plan for dealing with arguments. You wouldn’t waste precious minutes of your vacation fighting. Learn to put a hold on it, especially if you are a couple who fights about the same things over and over again.

Key Pointers

  • When planning a weekend getaway with your boyfriend/girlfriend, keep your trip short and make sure you are on the same page about the budget
  • Start planning well in advance and divide responsibilities
  • Give each other some space and know that it is okay to be laidback
  • Be open to trying new things and be willing to compromise
  • Pack light and defer all pending arguments until after the trip is over
  • Travel will bring out a different version of your partner (it could even be a side you didn’t know existed), brace yourself for the unexpected

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 them. 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.” 

This article has been updated in October, 2022.


1. Should I go on vacation with my boyfriend?

Yes, you should. Going on a couple’s trip will help you to get to know each other better. You will also know if the relationship is meant for the long haul or not.

2. When should you take your first trip together?

OnePoll conducted a survey of 2,000 Americans who traveled with their partners and came to the conclusion that taking the first couple getaway 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?

When traveling with a boyfriend/girlfriend before marriage, definitely do not pack 10 pieces of clothing and 5 pairs of shoes. Pack the bare minimum you need, carry insurance and emergency medicines, and travel light.

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