The First Holiday Together

Travelling together for the first time can sometimes be a scary prospect – how do we choose where we are going, the sleeping arrangement ordeal, how do we pay, do we want things planned for every single second.

couple sitting by lake and amazing mountains

This trip is a huge milestone, regardless of what the occasion is. However, to ensure that it runs smoothly and there is a limited amount of stress, here are some helpful pointers for your first trip together.

The Proposal (no, not that kind)

Sometimes, the hardest prospect of travelling together for the first time is proposing the trip in the first place. You feel like you’re ready for it but you don’t know if they are on the same page? Is it too soon?

Unfortunately, because everyone runs on their own timeline, there is no set amount of time before a trip away becomes the next checkpoint. You have to work that out together. There is the option of surprising him or her with a holiday as a present which as a gesture would be very exciting but suss out first whether it’s something they would be interested in.

The Planning


As your first trip together, you are always going to remember it so you want to make it a good one. In terms of location, make sure it is something that has things to do outside of where you are staying. You probably won’t have spent this much time together before so you don’t want to feel cooped up in a complex, constantly stepping on each other’s toes. Make sure you look at destinations that have lovely towns and restaurants you can walk to or boating trips for the day.

The travelling

There’s nothing worse than a flight that completely messes up your night’s sleep or arriving at the airport and there’s no transfer booked to the hotel. To ensure your holiday gets off to the best start, try and choose social flying hours and have everything organised so you don’t upset your partner.


As your first trip together, you want to make it special. Nothing says romance like booking a beautiful, sea view dinner on your final night or fancy, candlelit drinks – make the effort and plan ahead a little surprise.

Also read: Does ‘giving space’ actually work?

The Days

You’ll never be with each other more than when you are on holiday – day and night you are together. This can be a little worrying if it’s your first trip so here are somethings to keep in mind.

It’s okay if you want to do things separately

In fact, it’s encouraged. If she wants to go to the spa for a little bit then it’s not a personal jab at you, it’s just a healthy hour away to regroup individually.

Listen to each other

Some people want to sit by the pool, other people love the beach. While you both want to have a great holiday, make sure you communicate and do what you both want on different days so everyone has the best time.

Look out for other couples

Remember the pair who were on the boat trip with you the other day? They would be a great laugh if you had cocktails with them at the hotel bar before dinner. Socialising with other people can remove the pressure a little bit of being in each other’s pockets constantly and you can also make some great friends.

No work

Put the phone down. Nothing kills the mood more then you constantly checking your work emails or just sorting out ‘one last thing from the office’. You are on holiday together because you are excited to focus one-on-one – no work allowed.

Sort out the money issue

You both will want to pay for yourselves probably so sort all the big things beforehand – flights, hotel, transfers. Then, for the holiday, it may be an idea to have a kitty for all the things you are sharing – hotel drinks, dinner, ice creams, activities. Maybe each put in a certain amount and that is what this comes out of. Then, when it comes to individual purchases – postcards for home or that hat that you’ll probably never wear again – you can have your own money to use and this removes any awkward conversations.

Also read: London date ideas girls love

Ultimately, know that a holiday together is a really exciting next step and shouldn’t cause you stress. Just make sure that you have everything planned beforehand so that you can really enjoy the trip and focus on each other.

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