Holiday planning

Travel – holiday planning and preparations

I don’t know about you, but I love to have events in my diary to look forward to – and holidays are no exception. We generally have an idea of the trips we’re planning over the next 6-12 months and as the dates approach we firm up our plans. Holidays, by definition, should be positive experiences, but they can sometimes be stressful.

As a follow up to my previous holiday article, this one is all about the practical aspects of holiday planning and preparation. Many of these apply to travellers of any age, but I also include some age specific considerations. I’ll look at where and when to go, the booking process, travel companions, timing and other related topics.

Where to go

You may already have an idea where to go e.g. from working down your bucket list, returning to a familiar destination or from recommendations. You may even be lucky enough to have access to a second home somewhere. Alternatively, you may need some inspiration. There is a ton of information online including quizzes to help you decide, but I’m not sure how helpful these are.

When to go

Whilst some of us are tied to school holidays and work constraints, as you get older there are possibly fewer time constraints. You can plan breaks outside the popular school holiday periods to avoid the additional costs and crowds. This doesn’t always guarantee good weather, but this is typically out of our control anyway.

A colleague of mine and his wife, in their late 50s, take 3 holidays a year in the May-Sept timeframe. They book in advance, benefiting from discounts, and avoid school holidays.

Booking process

Many people book holidays online, although there are still opportunities to book by phone or even in travel agencies. This probably has as much to do with customer preference as well as the type of travel booking  e.g. package v flights only. There are also discussions around the deals that you can get in branches versus online. This has become more evident in recent years as some of the larger agents have closed stores, questioning the future of branches as a method of booking travel.

There are also wide choices available for online bookings, partly depending on the type of holiday e.g. package v piecemeal booking. You can book directly from a travel agent’s, airline’s or hotel’s website, or alternatively via comparison sites for each type of booking. I’ve included some examples below.

Package holidays – travelsupermarket  holidayhypermarket

Flight – article comparing flight comparison websites

Hotels –

As reviews are easily available these days, it’s advisable to check out other customers’ experiences in advance via TripAdvisor or the like.

Before booking your next holiday, you may want to look at the following guidance to get the best deals as well as specifically on last minute deals. There’s also some great general tips on holiday booking from this insider guide.

Finally, as holidays aren’t one-size fits all commodities, it’s worth ensuring you fully understand what you’re actually buying i.e. what’s included and what’s not, upfront, so there are no surprises further down the line.

When to book

There are often discounts for ‘early bird’ bookings and sometimes when booking at the last-minute. This probably depends on how far in advance you are planning to go and whether you have a specific idea of where and when you want to go etc. You can get some ut booking late isn’t for the faint hearted or picky travellers, unless you can be flexible on your dates.

I’ve moved from being a medium-late booker (approx. 1-2 months before travel) to an early bird. This is partly driven by the constraints of the school holidays, as well as knowing more about what we want.

Travel companions

Who you chose to go with can also be a key consideration. There may be no question but to go with your spouse, family or friends, if you have them, but it could also be interesting to do something on your own or with an organised group. This could especially be of interest if your circumstances have changed.

Another colleague separated from his wife. He now enjoys an annual cycling holiday in the Canaries. He goes on his own but often meets up with other likeminded souls: enjoying time alone, but also meeting new people along the way.

My late great aunt enjoyed several organised tours to Canada as a widow. She sometimes travelled with a friend but also met others on her trips.

Other considerations


As we get older there’s more to consider when purchasing travel insurance, including age specific premiums. Trip insurance, bought to accompany the holiday, might work out costlier, so you may want to compare against the cost of annual insurance if you are planning for multiple trips. Beware though, there are medical and other exclusions that you should be aware of before travelling.


If you take regular or ad hoc medication (prescribed or over the counter) it may be advisable to take this with you in case you’re not able to get this when you’re away. You may need to get extra in case you get a surprise flare-up or are delayed in your return. It’s also worth checking any restrictions in the country you’re travelling to e.g. opiate medications are illegal in some parts of the Gulf. This probably becomes more important as we get older and we tend to take more medication. More than half of 65-74, and more than 70% of those aged 75 and over, take at least three prescribed medicines on a weekly basis.

You may also want to consider the need for any medications specific to travelling e.g. vaccinations, malaria tablets etc. This is especially important for older people who may be at higher risk.

Mobility and accessibility

If you, or any of your party, have any concerns in this area, it’s advisable to check this out in advance. This information should ideally be available at the time of booking or there should be someone that can be asked. This will obviously be much easier to do up front, rather than having to negotiate this at the time and place (maybe even in a foreign language) and could alleviate stress and bother for all concerned.

Health and emergency services

Familiarise yourself with the health and emergency services in the destination. You never know if or when you may need these in case of illness, accident or another emergency. On arrival, check out the evacuation points and processes.

Dietary requirements

Our diets are becoming increasingly complex due to a combination of scientific discoveries and health trends. If you have limited or specific dietary requirements, check in advance whether these can be catered for. Often this is a case of advising of allergies and intolerances, and many places, both in the UK and abroad, are becoming better at dealing with this. If not, opt for self-catering or research what you will be able to eat in advance.

Passports & Visas

If you are travelling abroad you will need a passport. Make sure that when you travel this is not only in date, but also has the relevant remaining validity period for wherever you are travelling. Its also advisable to check if Visas are required for your destination, type of trip or length of stay, to avoid any disappointment and delay when you travel.


If you are travelling to another European destination, you will need an EHIC (European Health Insurance Card) to ensure you have suitable medical cover when abroad. This is a plastic card which replaced the old paper E111 document. You can apply for these online – either via the free NHS site or via other portals for a fee. A card is required for each person travelling and lasts for 5 years.

Foreign Currency

If you are travelling to a country which uses a different currency, it’s advisable to make some preparations. You could rely on your debit or credit cards for drawing cash or paying in country, but exchange rates aren’t always favourable. Some people prefer cash, to help them budget, but you could also consider using a prepaid travel card to help lock in exchange rates, assist with budgeting and for enhanced security.

Language issues

We are so fortunate being English speakers. If you are going to a foreign-speaking country, try to at least familiarise yourself with a few basic words and phrases.

Travel Anxiety 

Even the thought of travel can make some people anxious. If you’re one of those, check out this guide   on how to deal with the travel anxiety and stress that can be exacerbated by the holiday season.


Holidays, by definition, should be enjoyable, but we also know that travelling can also be stressful. With some ‘prior planning and preparation’ hopefully this will encourage you to do some preparation in advance to help alleviate some of the stressful parts.


Thank you for reading. For more interesting articles, visit my blog at to learn more.