Based In London

James O Leary

Available for new enquiries

It's Nice To Meet You

Travel. Tailored by a human. Enjoyed by you.
I work full-time planning travel. Let’s make sure you don’t have to.
Based in London, I’ve worked in the Travel industry for over 20 years.

Travel is the most enjoyable and most powerful learning tool we have as human beings. Travel enables us to learn about ourselves and the world around us. It bridges cultures, enriches lives and taking a break, however long, protects our mental health.

Now for all the benefits that Travel provides, planning it properly can be confusing and stressful, and most of all TIME-CONSUMING! This is where working with a personal Travel Counsellor like me comes into its own.

Travel Counsellors is a world-leading, award-winning, independent travel company offering 100% financial protection, 24/7 care whilst you are travelling and access to a community of Global travel experts, who deliver exceptional experiences, and great value to customers. We are experts in saving you time and lowering stress levels. From the minute you start researching, to when you get home. No one will put more thought and care into your travel plans than us.

Booking with Travel Counsellors is not like booking with a regular travel agent - online or on the high street. Think of us more as your bank manager but for Travel, and obviously a lot more fun. Ensuring that you invest wisely, get the best value and maximise your time away. You always get to speak to a human – be that me or our wonderful support teams. There are no automated phone lines or call centres with Travel Counsellors. You speak with a human every time with your own direct line.

I’ve been lucky to have travelled around the world many times over for both pleasure and business. I have lots of insights, recommendations, tips and tricks to share. If I had to pick my favourite destinations (it’s not easy) then I’d nominate Australia, South East Asia, the Far East, New York, California, Mexico, Italy and Greece.
So whether it’s a multi-centre holiday, a trip with friends, a romantic trip for two, a honeymoon, a surprise birthday, a trip to celebrate retirement, an around-the-world adventure and anything and everything in between – I have the expertise to create your perfect trip, every time.

EXPERT TIP: To get the most out of my service and expertise, and to save you lots of time in the long run, it is more effective and efficient to talk through requirements, rather than briefing solely by email. A conversation together will help us to capture your full requirements and enable us both to ask questions.

So whatever your enquiry might be, I’d be delighted to hear from you by phone, email or WhatsApp to arrange to chat – and to see where this journey takes us!

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My customer stories

Sent by Ashley Jordan

Last time we used an agent for a holiday my partner was not impressed. So when we were planning our big trip for next year, we were looking at booking with Trailfinders. We went in and talked to them and the agent called us back when he said he would but didn’t follow us up again. I thought we would never get our trip booked. Then James appeared in our lives and my partner and I met him over coffee and agreed he could research our holiday for us. James asked us lots of questions about our holiday likes and dislikes and went away to build an itinerary. The trip involves multiple flights, avoiding Easter expensive outbound flights, booking multiple local trips and excursions (where many were nearly full due to Easter falling whilst we’re away), ensuring my dietary requirements are catered for, juggling flights not running every day to some destinations and hiring a car. James has also sat with us for two Zooms and presented his suggested itinerary in a very engaging and professional way. My partner was very impressed and excited after that first Zoom and I breathed a sigh of relief. The deposit is now paid and the trip is confirmed. Trailfinders would not have done all the extra bits James did and we would likely have ended up in places not able to do the excursions we wanted. I totally recommend James and Travel Counsellors without hesitation.

Sent by Nigel Frank

The best I have ever used. I have a very definitive almost pedantic set of requirements and he met every one with a wonderful demeanor. We will use James again both personally and for our corporate requirements.

Sent by William Riquier

The service was extremely helpful, not just the booking but the after-sales service. I would have no hesitation in recommending James.

Sent by K Hewitt

Thanks again for everything. I really appreciated your patience and your help with this booking. Honestly, you’re the best agent I’ve worked with.

Sent by Craig Appleyard

Very knowledgeable and friendly. All our requests and changes were handled efficiently and the suggestions by James were also very well received. All in all a great service that I'd highly recommend.

Sent by L Wilkinson

James has been amazing!! So helpful and responsive. He is also a delight to deal with. I’m definitely using him for all my holidays!

My Blog

I absolutely live and breathe travel and I love to write about my experiences! Please take a look through my posts - you might find your own holiday inspiration.

Springtime in Palma de Mallorca and Port Soller

22 May 2023

If you would like me to design a trip just like this for you - drop me a line and let's see where the journey takes us! What reason for the Trip? It was my other half's birthday present Why Palma? It’s one of our favourite places to visit and we had not been for some time. The city is one of the most beautiful places to spend time in the Mediterranean, with excellent food and a great vibe. It’s

Contact Me

Whatever your holiday needs I'm here to help you, so simply give me a call or send me an email with your contact details on and I can get things started for you:

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