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!


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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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 also a great value destination, often overlooked by people who head to the beaches straight from the airport. Duration? A 5-night city break – Thursday to Monday. When? We travelled in March to escape the cold weather here in the UK and we were welcomed with temperatures in the 20s! Our itinerary? We spent 5 glorious days in Palma, Mallorca’s beautiful, buzzing capital city. We also took a day trip to the stunning towns of Soller and Port de Soller – more on that later... Where did we stay? A 4-star boutique hotel in Palma’s Old Town – Hotel Basilica. The rooms are lovely, and the hotel is spotless. the staff welcoming and helpful. The hotel even has a rooftop pool (with an honesty bar) with panoramic views of the city. A real gem of a hotel and one we’ll visit again. What did we do in Palma? We made the most of the springtime sunshine by wandering through the city at our leisure – keeping the step count topped up – soaking up the atmosphere and historical architecture. We did offset the step-count by eating and drinking our way around Palma as well – going back to old favourites and discovering new places along the way. Eating and drinking recommendations in Palma: There are far too many to mention every single one of them, so here is an excellent list to start with. Forn Projects - These people own 5-6 great places in Palma (and a vineyard outside the city too) and we’ve eaten very well at Forn and Koa. Tast Union – this is a busy, well-run tapas bar right in the centre of the city. La Boveda – a tasty Basque tapas restaurant in the Born district – was so popular that Mercedes Benz had booked it out for 2-3 nights running while we were there for events! Bar Abaco – not what you are expecting from the outside – generous cocktails in an eccentric venue on the inside Bar Nicolás – lovely and buzzy bar, open until late Coffee Fixes and Cake/Pastry addictions? Palma has that covered too! Mistral Coffee – best coffee in town, a real find in central Palma, with seating outside and in Fornet de la Soca – the best (and oldest) bakery in town – local speciality cakes, pastries and savouries – look out for the pigs and the fish (you’ll see what I mean). It’s also a brilliant place to create a picnic to then take to the beach if you have kids. Our day trip to Soller: Seek out ‘Tren de Soller’ - this is the best day trip on the island (if you are based in the South) and transports you from Palma, up and through the mountains, down into the stunning Soller valley by train and then onto the idyllic Port in Soller by tram. Our tips for the train would be - get to the station an hour before the time you want to leave (you can only buy tickets on the day) and then grab a coffee at the lovely little cafe there while you wait to board. Eating recommendations in Port de Soller: Bon Vi Restaurant - set back from the beachfront one block and the food was great - especially the John Dory I had. Patiki – right on the beach with fresh local and seasonal produce on the menu – is a great place to while away an afternoon with a chilled bottle of Rose or Verdejo and some delicious food.

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!