Ever wondered how some people take the most complicated trips yet seem utterly relaxed and laid-back throughout?  Chances are these savvy travellers always have incredibly detailed itineraries to hand and there are several steps you can take to ensure your trips are just as seamless.

How do they do it?

The secret to the perfect itinerary is down to perfect planning.  And, of course, personal preferences.  There’s no right or wrong way to take a holiday, experience a city break or tag time onto business trips.  Some of us like to get up and seize the day, visiting attractions and getting immersed in the local culture.  Others like to lie in, relax by the pool and sip cocktails all day.  Perhaps, like me, you enjoy a mixture of both.

But advance planning and having relevant information to hand can turn a great trip into an amazing one.  This isn’t a case of being route-marched from A to B.  It’s about being realistic, doing your research and covering all your bases.  You certainly don’t want to waste precious time doing it while you’re away.


Where to start

Once you have settled on a destination, the first step is to get outward and return travel booked.  This is particularly important if you’re taking a flight.  These timings set the parameters for the whole trip and can completely alter your plans.  A recent client hoped to travel to Italy but the limitations of the flight schedules, combined with hectic diaries, meant significant sacrifices to the itinerary.

Secondly, you need to secure accommodation for the duration of the trip.  It could be the same place throughout or different hotels every night.  Other elements of your stay will be built around this and inability to book a particular hotel may change your plans.


The fun stuff

Once you have these important details confirmed, you can move on to the more exciting elements.  Do you have a list of recommended places to visit from a friend?  Have you read a great guide book and found some suggested sightseeing spots?  Do you like to do similar things in each city you visit?  Are there any special events or celebrations taking place during your time there?  Jot some ideas down to create an initial framework of what you’d like to include.


The research

This is the part where Google becomes your friend.  When planning intricate trips for clients I start by plotting all the important locations on a Google map.  This includes the airport, the hotel and any places of interest they’d like to visit.  This makes it much easier to calculate travel distances, group activities together and search for nearby restaurants.

For each of the places you visit it’s helpful to know information such as:

  • Admission prices and special offers
  • Opening times and seasonal closures
  • Tour booking processes
  • Dress codes

With travel plans, you may also need to check information such as:

  • Parking arrangements at the airport
  • How long before a flight you need to arrive
  • What the baggage allowance is
  • How to get from terminal X to terminal Y in the airport and how long it takes
  • What the best option is for transferring from the airport to the hotel
  • What time breakfast is served at the hotel
  • The check out time

All of these details can be noted in your itinerary and allow you to factor in realistic timescales every step of the way.


Other things to think about

As well as the points above, here are some examples of other things you may need to consider: 

  • Having a range of options available for wet and dry weather
  • Not being able to fly within 24 hours of activities such as scuba diving
  • Cutting flight times too close to prepaid excursions, cruise departures and connecting flights
  • Booking ahead for popular restaurants
  • Catering to specific dietary requirements
  • Checking seasonal opening dates and times.  Is that ferry to a tiny, remote island actually running?

Expect the unexpected and keep it flexible

Try not to plan every minute of your trip and be prepared to build in changes.  How prepared you want to be will depend on your travel style.  For some, things like having the number of their relevant country’s embassy noted down provides a certain level of reassurance.  You never know when you might find yourself without a mobile phone, Wi-Fi or an English-speaking aide!



PLEASE, please make sure you have the appropriate visas, travel insurance and, of course, a current passport in place.  And make sure the latter has enough spare pages and at least six months left to run.  It’s always a good idea to let a member of your family (or ideally your PA) have copies of important documents in case you get into any difficulties (stolen bag, lost phone etc).  I would strongly advise having copies accessible by email as well.

If you’re planning your trip well in advance, set a reminder to reconfirm necessary aspects at an appropriate time.  For example, entrance prices may change with a new year and small businesses might close for refurbishment at quiet times.

The format of your itinerary is entirely down to personal preference.  Some clients prefer a separate document with just the core travel details noted in their diary, others like to use apps such as TripIt or Google Trips.  There are many options and creating your own document may allow more flexibility for information you wish to include.


My final tip

Whether for me or one of my clients, I always try to put myself in the shoes of the person making the trip and walk through EVERYTHING they may need to know along the way.  You’re unlikely to cover every eventuality but bear in mind, as Benjamin Franklin said, “failing to plan is planning to fail”!


Happy and safe travels!


If you’re overwhelmed at the prospect of creating the perfect travel itinerary, or simply don’t have enough hours in the day, please get in touch for some advice on how a Virtual PA could assist you.




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