James O Leary

My expertise

Caribbean
Japan
South East Asia
Sri Lanka
Multi - Destination
Group Celebrations
Australasia
Safari

I'm based in

London

Available for new enquiries

Award Winning Tailormade Travel

Amazing travel experiences, crafted with care in London and Surrey.

Part of the award-winning team at Travel Counsellors, I am London and Surrey-based, with over 20 years of experience designing tailor-made holidays, luxury escapes and complex itineraries. From your first idea to your safe return home, I plan your travel full-time, so you do not have to.

Why work with a personal Travel Counsellor?
Travel is one of the most powerful ways to learn, reconnect and reset, but planning it properly can be confusing, stressful and time-consuming.
Working with a dedicated, human travel expert means you enjoy all the benefits of travel without the overwhelm.

Booking with me is not like using an anonymous online travel site or a high-street shop. Think of me as your personal travel advisor, helping you invest wisely in your holidays, so you enjoy exceptional value, memorable experiences and complete peace of mind. You always speak to a real person: no call centres, no automated phone lines, just direct contact with our dedicated support teams and me.

As a Travel Counsellor, I offer:
• Personal, one-to-one travel planning tailored around you
• 100% financial protection and 24/7 support while you are away
• Access to a global community of travel specialists and trusted partners
• Thoughtful, joined-up itineraries that maximise your precious time away

I specialise in:
• Tailor-made, multi-centre holidays, honeymoons, and complex itineraries
• Safaris, including for first-timer families
• Group celebrations such as milestone birthdays and retirements
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Frequently Asked Questions
What does a Travel Counsellor do?
As a Travel Counsellor, I offer a fully personalised travel planning service. I design tailor-made holidays, luxury escapes and multi-centre itineraries based on your preferences, then manage every detail from initial ideas and quotes to booking, travel documents and support while you are away.

Why should I use a personal travel advisor instead of booking online?
Booking online can be time-consuming and confusing, especially for complex or luxury trips. Working with a personal travel advisor means you get expert guidance, trusted recommendations, financial protection and a single point of contact who knows you and your travel plans inside out. When trip plans go wrong, having someone like me in your corner to fix problems is invaluable.

Do you only work with clients in London and Surrey?
No. I am based between London and Surrey now, but I work with clients across the UK and beyond, including Singapore, Mexico, Australia, Canada and the USA. We can chat by phone, video call, email or WhatsApp so you can benefit from a tailor-made travel service wherever you live.

What types of holidays do you specialise in?
I specialise in tailor-made and multi-centre holidays, luxury honeymoons, romantic getaways, trips with friends, milestone celebrations and around-the-world adventures. Popular destinations include Australia, New Zealand, Southeast Asia, Japan, Sri Lanka, the Caribbean, Mexico, the Indian Ocean, Africa, Italy and Greece.

How does your travel planning process work?
We start with a conversation about your ideal holiday: dates, budget, destinations, pace and any must-haves. I then research and design a bespoke itinerary, refine it with your feedback, confirm your bookings and provide all documentation and support right up until you return home.

Do you charge a fee for your tailor-made travel service?
In many cases, my earnings are built into the travel arrangements I book for you. If a planning fee is needed for a particularly complex itinerary, I will always explain this clearly in advance so you can decide how you wish to proceed.

Is my money protected when I book with you?
Yes. Bookings made through me come with full financial protection and round-the-clock support while you are travelling, giving you peace of mind from the moment you confirm your trip until you arrive back home.

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Explore my guides and blogs

Why Parents Must Book UK School Holiday Trips Early: The Real Cost of Leaving It Late

Why Parents Must Book UK School Holiday Trips Early: The Real Cost of Leaving It Late

If you are a parent, you already know that travelling in the UK school holidays can feel like a strategic mission. You are trying to keep the children happy, secure the right destination, fit in with work commitments, and protect your budget at the same time. Yet every year, many families wait too long to book their school holiday trip, only to discover that the best options have sold out or the

18 May 2026 5   min read

Why I’m Proud to Be Part of an Award-Winning Travel Company

Why I’m Proud to Be Part of an Award-Winning Travel Company

When it comes to delivering exceptional travel experiences, few companies can match the consistency and credibility of Travel Counsellors. Over the years, the business has earned an impressive collection of awards across customer service, innovation, workplace culture, and industry leadership—cementing its reputation as one of the UK’s most respected travel brands. In this blog, we take a closer

14 May 2026 5   min read

Choosing the Best Safari for You: A Travel Counsellor’s Guide

Choosing the Best Safari for You: A Travel Counsellor’s Guide

Planning a safari is one of those “pinch me” trips: sunrise over the savannah, lions padding silently through the grass, the sound of hippos grumbling at dusk. But with so many options and destinations, it can quickly feel overwhelming for clients trying to choose the “right” safari.

13 May 2026 5   min read

Springtime in Palma de Mallorca and Port Soller

Springtime in Palma de Mallorca and Port Soller

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

22 May 2023 5   min read

What my customers say

James always seems to understand exactly what sort of holiday or travel I am looking for, however limited the brief from me is!

Claire Powell

London

10 out of 10! Already recommended to lots of people!

Mary Porter

Edinburgh

Very friendly, helpful, and knowledgeable, and came up with a great itinerary that I couldn't have put together myself.

Michael Clarke

Epsom

I would highly recommend James to anyone wanting to book a holiday. So professional, knowledgeable, and lovely, James made a task I usually find stressful, effortless! Will use him for every booking from now on.

R Furlong

South West London

I would highly recommend James to anyone wanting to book a holiday . So professional , knowledgeable and lovely , James made a task I usually find stressful , effortless ! Will use him for every booking from now on .

Adel Thomas

London

The process of discovering appropriate options was speedy and thorough, and the inevitable back-and-forths while contemplating the options were met with patience and agility. First-class all the way, highly recommended.

Jerry Caron

South West London

James was fantastic - super helpful. I couldn’t have booked the trip without his expertise. He saved me hours and hours of work!

Rosalind Doye

South West London

James is so helpful, he took the time to really understand what we wanted but also what ideal looks like for us, we were really impressed with the approach. Thanks!

Rebecca Hall

Surrey

We recently went on a 5-week trip arranged by James. There were an awful lot of moving parts, including 14 flights (including one scenic one), 1 helicopter ride, 2 boat excursions, car hire, 1 train ride, and 14 other day trips /excursions, as well as 13 hotels. In short, there was a lot that could go wrong. James was there every step of the way, ensuring that we had checked in, checking us in if we hadn’t, answering any questions, and following up where excursions were curtailed or cancelled. He also sent us links to things to do and places to eat in locations where we didn’t have excursions booked. It was fantastic knowing that we had James and the TC team behind us if something went wrong. I totally recommend James and Travel Counsellors without hesitation, whether it’s a a five-week trip or a two-week annual holiday.

Ashley Jordan

London

I will be recommending James O'Leary at Travel Councellors to anyone considering a bespoke touring experience. His in-depth knowledge helped us reach our multiple goals for our holiday.

Lawrence Holley

Surrey

We recently returned from a ‘once in a lifetime’ trip to Sri Lanka that we booked through James O’Leary from Travel Councillors. Throughout the booking process James was an excellent communicator – really drilling down into what sort of holiday we were looking for, what activities we would enjoy, the ages of our children, what they enjoyed and so on. After numerous video calls, James managed to narrow things down, and eventually came up with the perfect trip – five hotels and a private villa, with a guide who was with us for the whole trip. We also had various excursions – jungle safaris, whale watching, snorkling with sharks and turtles, as well as visiting a tea plantation and climbing 1,200 stairs attached to a huge rock to watch the sunrise. James’ attention to detail was incredible – one our daughters is autistic, so little things like booking a quiet room to go to on arrival in Columbo, and using the VIP departure terminal on the return were an absolute must, but also the tiny things, like asking us if we would like still or sparkling water in the car were equally taken care of. Overall I cannot fault the booking process, or the execution of the holiday itself. It will live on in our minds and the minds of our children for many years to come.

P Dyson

London

Excellent service and patience with attention to detail - thank you, James! We’re looking forward to our trip!

Amanda Blunden

London

James was absolutely fantastic during the process, simplified the options, used his clear experience in these scenarios, would highly recommend him!

Declan Clarke

Surrey

James has been an absolute joy, looking forward to our trip being as stress-free as it was to book!

Charlotte Gibbons

Surrey

James came highly recommended, so we were not surprised by how helpful his service was. The taxi pick-ups worked very well, the hotel was excellent, and our tour guides were also. We were impressed that James had communicated with our taxi driver from Heathrow when our flight was due in 50 minutes early, so that we were not delayed unnecessarily. Very many thanks.

Blaise Hardman

London

Very thorough, friendly, considerate, and a pleasure to deal with!

Lucy Clarke

Surrey

James is simply brilliant and so patient. We’ve used his services a few times now and would highly recommend him.

Marie Giannini

London

He is amazing :) Always helpful and leans in to 110%

Karen Leader

Mexico City

James simply takes all the stress out of holiday booking; he thinks of everything! He particularly makes the time to get to know you and what you are looking for in a holiday, and then curates a fabulous shortlist to choose from, so you’re not overwhelmed. He’s my travel Angel!

Alison Ineson

London

James is friendly, helpful, and knowledgeable. Always available to assist.

Kim Seah

Singapore

This is the second time we have used James to plan our holiday and once again he came up trumps!! We also have other friends who have used him and they also sang his praises. He listens, comes up with some great suggestions and isn't pushy on prices!!

Jonny Dyson

Surrey

James is so helpful and efficient, I would highly recommend using his very professional service!

Gemma Blackburn

Edinburgh

James has been very helpful and taken lots of time in helping us to book a complicated trip. Thank you, James!

Melanie Getto

Knutsford

We love him! Always on top of every detail with 100% care.

Karen Pepper

London

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.

Ashley Jordan

London

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.

Nigel Frank

London

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

William Riquier

Singapore

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.

K Hewitt

London

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.

Craig Appleyard

Lancashire

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!

L Wilkinson

London

Discover the world with me

We’ve been awarded a King’s Award for Enterprise 2026 in Innovation

We’ve been awarded a King’s Award for Enterprise 2026 in Innovation

Award-winning innovation. Powered by people.

14 May 2026

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Tailor-made for you

Your holiday isn’t just a trip away. It’s a longed-for escape, time to reconnect with loved ones, or a dream adventure you never thought possible. That’s why I take the time to truly get to know you and understand your hopes and expectations, then use my experience, connections and passion for the destination to create a trip that makes those dreams a reality.

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Personalised service. Always

When you plan a holiday with me, you’ll be given my personal mobile number from the very first call. I’ll listen to your thoughts and ideas like I would a friend and arrange accommodation, activities, and flights that are all personalised to you. And I’ll share my personal tips and recommendations, so you can experience the true beauty of each destination.

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Stress-free travel, and more time
for what matters most

I believe your time away should be stress-free, easy, and seamless from start to finish. So, I take care of all the details for you - from ATOL protection, insurance, and flexible payments to access to the myTC app, which keeps everything in one place.

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Support when it matters most

If the unexpected happens, you can rest easy, knowing that I’ll handle any last-minute changes, flight cancellations, or disruptions before you even pick up the phone. So you always feel happy, carefree, and ready to make the most of every moment.

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+44 207 112 8135

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