There are few things more exciting than planning a holiday with such an endless list of possibilities. Whether you’re looking to relive something you have experienced before or looking to try something completely different and new, each trip creates anticipation and excitement. But in a world now where everything is customisable and there are so many options, it is the details that matter. From the overall location and accommodation, to the flight options, transfer arrangements and day to day plans, it can become overwhelming, especially when organising for someone else or a bigger group. Experienced travel operators such as True Travel have developed a knack for mastering this planning.

With fulsome familiarity of major destinations and expert knowledge of those a little off the beaten track gems, True Travel curates and crafts entirely bespoke itineraries tailored to their client’s every want and need. We sat down with our Global Sales Director, Pete Trangmar, and Commercial Director, Molly Pigott, to discuss everything you really need to know and consider when organising your client’s or your own holiday.

The Keys to a Magical Holiday

Planning your or your employers travel starts with understanding as many of the five Ws as possible; what, where, when, who and sometimes the overlooked why. Each W holds the key to unlocking something magical within a trip, a focal point that the planning can centre around.

It may well be that you don’t hold all the answers for the 5 Ws, but that is ok. What is important is that there are at least some covered.

Take the Where. It is not uncommon for people to be unsure exactly where they want to travel to, but if they know What it is they want to do or experience, Why they want to go or When they wish to travel the answers can be found with some expert help or research.

Likewise, the When can be determined by other answers within the five Ws, and sometimes some flexibility on dates can help when it comes to ensuring you get the very best experience, whether that is due to seasonality or availability. It is important to highlight when dates are fixed though, as this will help focus the planning.

Knowing upfront on Who is travelling helps answer a lot of questions. This can vary from knowing the number of rooms or flight seats needed, or whether it is a family or older guests travelling so special arrangements can be made.

The Why is possibly the most important answer of the five to really set the travel experience apart. It is the answer that gets to the heart of the reason for travel, where details and touches can be focused around, how the lifelong memories are going to be made. Not understanding the dream ahead of planning risks disappointment in the experience itself.

From a safari in Africa to see the big 5, wine tours across Europe or a diving experience in Asia, what seems like a fairly straightforward brief can become a list of endless questions and possibilities. Peeling back the specific motivations for travel, like seeing the particular animal out in the wild or seeing a particular monument in a city, can help guide the process considerably.

Some of the best and favourite holiday experiences we have created have involved the most specific requests, like wanting a candlelight dinner whilst watching the sunset behind the Eiffel Tower, or a sunrise tour of Taj Mahal. Clients have wanted to learn specific recipes and take part in cooking classes with local families. With clear guidance and good planning, almost anything is possible.

Logistical Considerations

From a planning point of view, before anything can be booked some decisions will need to be made on the Where, What, Who and When, even if they are not known initially. Aside from a fundamentals of the destination / location and dates, some things you will need to consider include:

• Knowing where you’re going to be travelling from and the preferred mode of transport, for both the main route, and transfers (where there are multiple options available). Train routes are constantly improving and more travellers are choosing do take advantage of the more scenic mode of transport when travelling to or around their chosen destination.
• A preference for travelling overnight or through the day and direct or in-direct flights. Whilst this may be restricted by the options available, there is often a choice of routes and flight times available. These options will cater for you if you’re looking to arrive first thing to get a full day or stay avoid overnight travel depending on the preference.
• Special room arrangements, like inter-joining rooms or rooms on the ground floor. These choices may help determine the accommodation choice or type of room required.
• Dining preferences. Particular tastes or dietary requirements can be catered for very easily and with a good amount of warning, tips and suggestions on local restaurants and nearby attractions can be made and built into the travel itinerary.
• Visa requirements. As dull as it is, it is important to ensure this is planned for all travellers. If they are required, they should be handled directly through the country’s visa scheme and all individual travellers. While it is possible to apply for visas on behalf of someone else, it is best done by the person travelling to ensure all details are correct. 

Elevating The Experience

As important as getting down to the Why of the trip are the small details that can make the biggest differences. From working around particular allergies, to…  

Past Experiences

There is much can be learnt from the previous travel experiences of you or your employer and reflecting back on past holidays to consider what was and wasn’t enjoyable can help set the tone for future trips. Some questions to consider include:

• What types of accommodation have been used on previous trips? Is the preference for exclusive-use properties with direct beach access, or the charming atmosphere of a boutique hotel? Are there particular brands or styles of hotel that are preferred or to be avoided?
• What experiences were raved about long after they returned or wish they hadn’t bothered with? Were they close up, private encounters, part of larger group experiences, deeply experiential, more relaxed, active, relaxing. 

Special Requests

If travelling as a large group, have everyone’s needs been taken into account? Are there any food allergies or aversions? Is it a multi-generational trip with varying needs and abilities? These needs are often overlooked when communicating with just one person, and can be difficult to address if not identified early. Plans can be easily made and adapted if these details are known early, and can really make the difference in the comfort and experience of the trip to those who depend on it.

When to book and start planning?

Ask travel specialists if you should book early and they’ll all answer with a resounding ‘yes’. The general rule is the more specific and weather dependent the request, the earlier you’re going to want to get your plans confirmed. Otherwise, be prepared to compromise. Our Commercial Director, Molly, advises between 12-18 months for truly tailored and personalised travel, although a lead time of four to six months is usually manageable for European holidays and seven to nine months for long haul travel.

What are the risks of booking late?

Booking later often comes with higher prices, especially for flights. Accommodation options also become more limited, particularly for those with special requirements. Additionally, there’s less flexibility in scheduling—top guides and premium experiences are likely to be fully booked or only available on specific dates.

Considerations for booking later

That being said, there are some benefits of waiting to book. One being flexibility—the ability to adjust your schedule or plans as needed. If you have no destination in mind, the world can truly be your oyster. The other being price—waiting until the last minute when hotels and airlines cut prices to fill rooms and seats. However, there comes a point when dates and arrangements need to be confirmed. If left too late, it can become challenging to confirm bookings.

Final Thoughts

Planning travel doesn’t have to be daunting, but for those dream experiences it really is worth enlisting the support of experts. There is so much to consider, from sorting the travel arrangements and accommodation, to booking the individual events and experiences. Travel experts and tour operators are there to ensure you get the support and advice you need, as well as potentially get better rates, more flexibility and exclusive experiences you may not be able to access directly.

Whether you are starting to think about travel, or knee deep in plans and just looking for a bit of advice, the team at True Travel are happy to help.