James O’Leary - Travel Counsellors

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James O’Leary - Travel Counsellors

Travel. Tailored by a human. I plan travel full-time, so you don’t have to.

02/09/2026

This is a difficult one.

But if I had to choose, I’d go for autumn.

Spring gets most of the attention because of cherry blossom season, and understandably so. Seeing Japan covered in pink is one of those travel experiences that deserves its reputation.

But autumn brings something completely different.

Temples surrounded by red and gold leaves.

Cooler days that are perfect for exploring.

Beautiful gardens changing colour.

And bowls of ramen that somehow taste even better when there’s a chill in the air.

I’d love either.

But there’s something about Japan in autumn that appeals to me just a little bit more.

So, which would you choose?

🌸 Japan in spring

🍁 Japan in autumn

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

01/09/2026

If food was one of my priorities, I’d choose Barbados.

The beaches are obviously beautiful, but what I really like about Barbados is how easy it is to make eating out part of the holiday.

You can have freshly caught fish somewhere completely relaxed at lunchtime, then dress up for dinner at an excellent restaurant overlooking the sea that evening.

And I think that’s important.

Because if I enjoy good food, I don’t necessarily want to spend every night eating in the same hotel.

Barbados gives you choice.

Fish fry at Oistins.

Beach bars and rum shops.

Restaurants along the west coast where dinner can easily turn into an entire evening.

It’s an island where I’d actively encourage people to get out of their hotel and explore.

There are Caribbean islands I’d choose for other reasons.

But if you told me food really matters?

Barbados would be very difficult to beat.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

31/08/2026

The question I hope every client asks me

“What would you do?”

I love that question.

Not because I think there’s one perfect answer.

But because it lets me move beyond what’s popular and talk about what I genuinely think will make a better holiday.

Sometimes I’ll suggest staying an extra night instead of adding another destination.

Sometimes I’ll recommend the smaller hotel over the famous one.

Sometimes I’ll say the room upgrade isn’t worth the money.

And sometimes I’ll recommend somewhere that wasn’t even on your original shortlist.

That’s because my job isn’t just to find holidays.

It’s to help people make the right decisions.

The more I understand how you like to travel, the more personal my recommendations become.

So if you’re ever unsure…

Ask me what I’d do.

You might be surprised by the answer.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

30/08/2026

Why great holidays feel personal

The best holidays don’t feel as though they could have been booked for anyone.

They feel as though they were created with you in mind.

The hotel suits the way you like to travel.

The destination matches your interests.

The itinerary reflects whether you love exploring from dawn until dusk or prefer long, unhurried lunches and afternoons by the pool.

That’s why I spend as much time asking questions as I do making recommendations.

Two couples with the same budget could end up with completely different holidays.

Not because one is better than the other.

Because the right holiday is different for everyone.

For me, that’s what makes travel so rewarding.

It’s not about finding the “best” destination.

It’s about finding the one that feels right for you.

That’s when a holiday stops feeling like a booking…

…and starts feeling personal.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

29/08/2026

Lake view or sea view?

If I had to choose…

I’d go for a lake view.

The sea has an energy to it that I love.

But lakes have a calmness that’s difficult to describe.

Early mornings with the water like glass.

Mountains reflected on the surface.

Watching boats drift by while you enjoy breakfast on the terrace.

It all feels a little slower.

A little quieter.

That’s not to say I’d ever turn down an ocean view.

There’s nothing quite like hearing the waves from your balcony.

But if I could only wake up to one tomorrow…

I’d choose the lake.

What about you?

🏞️ Lake view

🌊 Sea view

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

28/08/2026

The travel advice I find myself giving most often

Don’t try to do too much.

It sounds simple, but it’s probably the piece of advice I give more than anything else.

It’s so tempting to squeeze in one more destination.

One more excursion.

One more hotel.

But every time you add something, you also add another journey, another check-in and another suitcase to unpack.

Sometimes less really is more.

I’d much rather help someone spend four nights somewhere they’ll fall in love with than two nights somewhere they’ll barely get to know.

The irony is, people often come home feeling as though they’ve seen more because they had the time to enjoy it properly.

The best holidays aren’t about fitting everything in.

They’re about coming home feeling like you made the most of every moment.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

27/08/2026

Why less planning can sometimes create better memories

I spend a lot of time planning holidays.

But one thing I almost always recommend is leaving a little space for the unexpected.

Not every hour needs an itinerary.

Some of the best travel memories happen when there isn’t a plan at all.

You wander into a café because it looks inviting.

Take a different street and discover a hidden square.

Stay a little longer because the view is too good to leave.

Those moments can’t be booked in advance.

They’re the reason two people can visit the same destination and come home with completely different stories.

Of course, the important things still need planning.

The right flights.

The right hotels.

An itinerary that flows naturally.

But once you’re there, don’t be afraid to put the map away for an afternoon.

Sometimes the best part of a holiday is the part you never planned.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

26/08/2026

Boutique city hotel or countryside retreat?

If I had to choose…

I’d go for the countryside retreat.

Don’t get me wrong, I love a great city hotel. Being able to step outside and explore museums, cafés and neighbourhoods on foot is hard to beat.

But if I’m looking to properly recharge, it’s the countryside that wins.

Waking up to birdsong instead of traffic.

Long walks without a destination in mind.

A cosy lounge, a great meal and nowhere else you need to be.

It’s the kind of place where you naturally slow down.

Of course, my ideal trip would probably include both—a few days exploring a city, followed by a countryside escape to unwind before heading home.

But if I can only pick one…

I’m choosing the countryside.

What about you?

🏙️ Boutique city hotel

🌿 Countryside retreat

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

25/08/2026

The holiday I’d recommend to almost everyone at least once

If I could recommend one type of holiday that almost everyone should experience, it would be a safari.

Not because it’s luxurious.

Not because it’s a bucket-list trip.

Because nothing quite prepares you for it.

You quickly realise that every game drive is different.

You stop checking your phone.

You start noticing the sounds, the smells and the excitement of never knowing what might appear around the next corner.

Then, after a morning in the bush, you’re back at a beautiful lodge for breakfast, with the rest of the day to relax before heading out again.

It’s an incredible balance of adventure and downtime.

I’ve spoken to so many people who’ve come home from safari saying exactly the same thing…

“I wish we’d done it sooner.”

For me, that’s the sign of a truly special holiday.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

24/08/2026

Why local recommendations beat guidebooks

Guidebooks are brilliant for the highlights.

They’ll tell you where to go.

What they can’t always tell you is where the locals actually spend their time.

The family-run restaurant that’s tucked away down a side street.

The beach that takes an extra ten-minute walk but is worth every step.

The café where everyone heads for breakfast.

The little wine bar you’d probably walk straight past if nobody pointed it out.

Those are often the moments people remember most.

I always encourage clients to leave room for those discoveries.

Ask the hotel concierge.

Chat to your guide.

Strike up a conversation with someone who lives there.

Some of the best recommendations don’t appear on page one of a search engine.

They come from the people who know the destination best.

And they’re often the ones that make a holiday feel truly authentic.

⸻

DM:

Email 📩: [email protected]

Call / WhatsApp: +44 207 112 8135

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https://www.travelcounsellors.co.uk/james.oleary/

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