Your first holiday together, without the drama

When is it time for a first holiday together?

When a shorter trip has already gone well. A holiday is days of each other's company, in someone else's bathroom, with delays, sunburn and decisions about dinner. That's a lovely test of a relationship, but it's a test, so it helps to have passed a smaller one first.

Good signs you're ready:

• You've had at least one night or weekend away, and you'd happily do it again.
• You've seen each other tired, hungry and fed up, and it was fine.
• You can talk about money without either of you going quiet.
• You both want to go, rather than one of you hoping it will move things on.

If you're not there yet, a weekend in the UK is a perfect halfway step. A seaside town out of season, a city break by train or a cottage near a good walk all work.

Start small, then go further

Build up in stages, the same way you did with dating. Each step tells you something useful about the next one.

1. A day trip. A long day out somewhere new, with a train or a drive either side.
2. One night away. A pub with rooms or a B&B, not too far from home.
3. A long weekend. Two or three nights, ideally with a mix of plans and free time.
4. A week, or a trip abroad. Once the first three have gone well.

Talk about money before anyone books

Have the money conversation before you look at hotels. It's much easier than having it at the airport. Questions worth answering together:

If your incomes are very different, choose somewhere that suits the smaller budget, or agree that one of you covers particular things. What matters is that it's said out loud. Whatever you agree, keep your own bank card and some money of your own.

Choosing where to go

Pick somewhere that gives you both something to do, and some room to do it separately. A place with walks, a beach or a town to explore means you're not relying on conversation for every waking hour.

Things to agree before you choose:

• Pace. Is this a rest, or a holiday full of plans?
• Rooms. A twin or double is a real question early on. Say what you'd like.
• Time apart. An hour each with a book, a run or a swim is healthy, not a sign of trouble.
• Travel. Long trips with someone new can be tiring. Shorter is kinder.

Passports, entry rules and health cover

Check the rules for the country you're going to on GOV.UK foreign travel advice before you book, and again before you go. For Spain and the rest of the Schengen area, GOV.UK says (as of 8 November 2026):

• your passport must have been issued less than 10 years before the day you arrive;
• it must be valid for at least 3 months after the day you plan to leave;
• you can usually visit without a visa for up to 90 days in any 180-day period;
• a digital Entry/Exit System is being rolled out, so you may be asked for fingerprints and a photo, usually on your first visit, and there may be delays at the border.

For health cover, the NHS says the UK Global Health Insurance Card (GHIC) is free and covers state healthcare in countries including those in the European Economic Area. It is not a replacement for travel insurance, so buy that too, and apply for the GHIC only through the official NHS site, because unofficial sites may charge a fee.

Taking children on holiday after a separation

If your children are coming, check you have the right permission before you book. GOV.UK says you must have the permission of everyone with parental responsibility for a child, or the court's permission, to take them abroad, and that taking a child abroad without it is child abduction.

The main points from GOV.UK:

• If a child arrangements order says your child lives with you, you can take them abroad for up to 28 days without permission, unless a court order says you can't.
• A letter from the other person with parental responsibility is usually enough to show you have permission. It should include their contact details and details of the trip.
• Carrying your child's birth certificate helps, and so does a marriage or divorce certificate if you have a different family name from your child.

Family law in Scotland and Northern Ireland is separate, so if you live there, check with a solicitor or Citizens Advice. And think hard before your new partner's first holiday with your children is abroad: our guide to introducing children to a new partner suggests building up slowly, and dating while you co-parent covers agreeing plans with your ex.

Staying safe when it's still fairly new

You'll probably feel completely safe, and that's good. A few habits still make sense on a first trip abroad with someone you haven't known long:

• Keep your own passport, bank card, phone and charger.
• Make sure your phone works abroad and you know what roaming costs.
• Tell a friend where you're staying and when you're due back.
• Keep enough money, or room on a card, to get yourself home if you need to.
• Be wary if someone you've only met online suggests a trip and asks you to pay for their ticket. That's a classic romance scam; our guide to spotting a romance scam explains why.

If it goes wrong

Sometimes a holiday shows you something you'd rather not have seen. If you fall out, take a few hours apart before you talk. If it becomes clear the relationship isn't working, be kind, be practical, and get home safely. It isn't a failure: it's exactly the information a first trip is for. If it knocks you, our guide to rebuilding your confidence is there when you're ready.

How Fish For Singles fits

Fish For Singles is for people starting again after a break-up, a divorce or a long while on their own, so a first holiday together might be further off than next summer. That's fine. Joining, making a profile and browsing are free, and reading and replying to messages needs a paid membership. Start with our guide to your first date in years, and plan the sun loungers later.