First solo holiday over 50? Here’s what nobody really tells you

For some people, travelling alone has always sounded exciting. For others, it was never really part of the plan.

Perhaps you travelled with a partner for years. Maybe holidays have always revolved around children, friends or family. Or perhaps there’s simply somewhere you really want to go and, despite plenty of enthusiastic conversations, nobody else ever seems quite ready to book it.

That’s often how a first solo holiday begins. Not with a sudden desire to reinvent yourself as a fearless solo traveller, but with a much more ordinary thought: I really want to go, and I’m tired of waiting for somebody else to be available.

If you’re considering solo travel in your 50s or 60s for the first time, there are a few things worth knowing before you go.

The booking can feel harder than the travelling

Strangely, one of the biggest hurdles often happens while you’re still sitting at home.

When you book a holiday with somebody else, there’s another person confirming the decision with you. You compare flights, send hotel links backwards and forwards and eventually press the button together.

When it’s just you, that final click can feel much bigger.

Questions that seemed manageable suddenly appear: What if I don’t like it? What if I feel lonely? What if something goes wrong? Will everyone think it’s strange that I’m travelling alone?

That uncertainty is normal. It also doesn’t necessarily mean solo travel isn’t for you.

Try separating the decision into smaller pieces. Rather than asking yourself whether you’re ready to become “a solo traveller”, ask whether you want to visit the place in question. Then look practically at what would make the experience feel manageable.

You don’t have to prove anything.

Eating alone is often the thing people worry about

Walking around a new place by yourself can feel liberating. Sitting down at a table for one can feel completely different.

If this is one of your worries, you’re far from alone.

The first time might feel a little unfamiliar, but it becomes normal remarkably quickly. Choose relaxed cafés and restaurants, sit somewhere you can watch the world go by, take a book if you like, or sit at a counter rather than a formal table.

And remember: most other people in the restaurant are thinking about their own dinner, not analysing yours.

That said, you may discover you like travelling independently but don’t actually want every meal to be a solo one. That’s an important distinction.

Solo travel doesn’t have to mean spending an entire week without company.

You’ll probably speak to more people than you expect

When we travel with somebody we know, it’s very easy to stay in our little bubble.

When you’re on your own, conversations happen differently. You ask somebody a question. You speak to the person beside you on an excursion. You chat to staff. Someone asks where you’re from.

That doesn’t mean you suddenly have to become wildly extroverted. You can still have plenty of time to yourself.

But being alone often makes you more approachable, and more likely to notice the people around you.

For many people, that becomes one of the unexpected pleasures of solo travel.

You are allowed to make things easy for yourself

There’s a strange idea that “proper” solo travellers must organise everything independently, stay somewhere adventurous and navigate every transfer themselves.

You really don’t.

Book the airport transfer.

Choose the nicer room.

Pre-arrange the first few days.

Join a small group for part of the trip.

Pay somebody else to organise the awkward bits.

You’re travelling for yourself, not sitting an exam.

Particularly if this is your first solo holiday after 50, removing unnecessary stress can make the difference between spending the weeks beforehand worrying and actually looking forward to it.

Private space matters more than you might realise

Company is lovely. So is closing your bedroom door.

If you’re considering a group holiday for solo travellers, check whether you’ll have your own room or be expected to share.

Having private accommodation gives you both options: you can spend the day exploring with other people and still have somewhere completely your own at the end of it.

For many travellers in their 40s, 50s and 60s, that balance is far more appealing than the traditional image of group travel.

Group travel and solo travel aren't opposites

There’s a big middle ground between taking a completely independent trip and joining a tightly scheduled coach tour.

You can make the decision to travel alone, book your own flight and arrive independently, then join a small group once you reach your destination.

You still get the satisfaction of thinking, I got myself here, without having to organise every transfer, dinner and activity by yourself.

It can be a particularly good introduction to solo travel if the thing holding you back isn’t the destination — it’s the thought of spending the entire trip alone.

That thinking is exactly what led us to create Flying Solo in Thailand.

From 3–10 March 2027, Jax and the Freedom team will bring together a group of travellers who are all arriving without a companion. Everyone meets in Phuket before travelling together to Koh Lanta, with private accommodation throughout and the main travel and experiences organised once the trip begins.

There are no couples and no established friendship groups arriving together. You’re not the one person walking into somebody else’s holiday.

Everyone has made the same decision.

Make it stand out

And no, you’re not too old

There isn’t an age by which you should have completed all the adventurous parts of your life.

People find themselves with more freedom at completely different stages. Children grow up. Careers change. Relationships change. Priorities change. Sometimes you simply reach a point where you realise that waiting for the perfect circumstances could mean waiting forever.

You don’t need to be fearless.

You don’t need to be particularly adventurous.

And you certainly don’t need to start calling yourself a solo traveller.

You might just need to decide that there’s somewhere you’d quite like to go.

And go.

Thinking about taking the first step? Explore Flying Solo: Thailand, 3–10 March 2027.