Planning a multi-country itinerary with guide books, computer, and notepad

Top Tips for Planning a Multi-Country Itinerary

How do you plan a multi-country itinerary and make it the ultimate trip? These top tips will help you plan a fantastic holiday like a travel pro.

You’ve booked your holiday leave and are looking forward to taking time off from your normal life.  You know you want to use that leave to have the best time possible.  You don’t just want to fly and flop, you want to experience different countries and cultures.  But what do you need to think about when planning a multi-country itinerary to make the most of your holiday?  Our top tips will help you plan the ultimate trip.

In This Post

  1. Decide what you want from your trip to make the best of the time you have available
  2. Consider the time of year when you will be travelling
  3. Plan how to travel between countries
  4. Know what the visa/entry requirements are for each country on your itinerary
  5. Research the currencies you will need
  6. Ensure you are aware of a country’s important legalities and customs
  7. Vaccinations
  8. Travel insurance
  9. Make sure you know if there is any time difference between the countries you’re visiting
  10. Check whether there are differences in electrical voltage/AC adaptors between the countries you’re visiting

1. Decide what you want from your trip to make the best of the time you have available

Ask yourself the following questions to help you decide what you want from your trip:

  • Which countries/places do you want to see?
  • Do you want to travel independently or with a company on a guided tour?
  • Would you prefer to plan the trip in advance or see what happens as you go along?
  • How much time do you have?

Which countries/places do you want to see?

You probably have an idea of the places you want to visit on your multi-country itinerary.  However, in the early stages we recommend being as open-minded as possible.  Researching where to go on holiday is the best part of planning and we guarantee you will discover new places that you’ve never considered before.  For example, whilst researching flights to Panama we realised we could easily include time in Miami to make a multi-country itinerary.  And whilst we knew we wanted to do a road trip in Slovenia, researching routes led to incorporating time in Italy and Croatia (see our post about this trip here).

Map with trip itinerary marked out
Our Croatia/Italy/Slovenia route

Do you want to travel independently or with a company on a guided tour?

Travelling independently, by which we mean designing and booking your trip yourself, is a lot of fun for some but a headache for others.  Some may prefer the security of a third party being responsible for all of the arrangements.  Others may feel this takes some of the joy out of travel.  It can also depend on where you are going.  For example, you may feel confident planning an independent trip to Canada but less confident about Alaska and choose to use a company for the latter.  You may opt to do something in between and use an agent to plan some of your trip and independently plan other parts.  Which you choose is a matter of personal preference and you should choose whichever allows you to enjoy every minute of your multi-country itinerary.

Would you prefer to plan the trip in advance or see what happens as you go along?

If you are travelling independently you may prefer to make decisions about your trip itinerary as you go along.  This gives you a lot of flexibility as it allows you to decide what to do as you go along.  For some, this is the only way to travel.  However, if you have limited time (as you will if you are fitting a trip into holiday leave) planning as you go along can turn a dream trip into a nightmare.  Deciding where to go and booking transport and accommodation on the move will eat into your holiday time.  In addition, bad timing may mean you can’t go where you want to go, especially if advance reservations are necessary. 

To an extent, the success of planning independently in advance will depend on the quality of resources available to you.  Ground transportation can be particularly difficult.  When we travelled across Japan by train we planned our journeys before we left the UK.  We chose to do this because we knew our inability to speak Japanese would mean we’d spend a lot of our time out there trying to work out how to get from A to B.  Unsurprisingly, we preferred to use that time enjoying A and B.  We were able to plan the trains at home using the brilliant

For some countries, detailed transport information will not be available until you get there.  Indeed, it isn’t always desirable to plan in so much detail because having some flexibility can make or break a trip.  If you plan everything and something goes wrong or there is a delay, what then?

We highly recommend looking at sample itineraries to get an idea of what you can do to.  Click on the ‘ITINERARY’ tag to see posts about our multi-destination and multi-country itineraries.

How much time do you have?

The time you have will dictate how much you can fit in to your multi-country itinerary.  For example, if you visit ten countries in two weeks how much time will you spend actually enjoying those places?  This is all part of deciding what you want from your trip. It may be that you only want to spend a few hours in each place before moving on to the next.  Alternatively, you may want to take things more slowly, spending longer in each place but not visiting as many destinations.

For ideas on how to use your annual leave to get even more time off for work for experiences like this read How To Maximise Your Annual Leave.

When planning a multi-country itinerary, it is important to factor in the time it takes to travel between destinations.  The example below illustrates why this is necessary:  

A maths question for you. It takes 75 minutes to fly from London to Paris.  How long does it take to get from the Tower of London to the Eiffel Tower? 

Aerial view of the Tower of London
How long does it take to get from here…

When you consider that most airlines recommend you arrive at the airport three hours before the flight you need to add on an additional 180 minutes.  At large airports you need to add on at least 45 minutes for the time it takes to disembark and clear customs.  Add on another 45 minutes if you have travelled with luggage in the hold.  A 75-minute flight has become almost six hours long and you’ve only gone from airport to airport!

Eiffel Tower from across the Seine
…to here?

2. Consider the time of year when you will be travelling


For most people, one of the most important considerations when planning a holiday is the weather.  This is easy when travelling to one place, you have a look at the average weather temperatures for the month in question. But what about when planning a multi-country itinerary?  The weather becomes more of an issue and you need to know what you need to pack accordingly. 

For winter sun holiday ideas read Top Winter Sun Destinations Around the Globe.

The weather may be very similar in the places you are going to, or it could be disparate.  For example, when we went from Miami to Panama to New York one March we encountered the full gamut of weather.  It was warm but extremely windy in Miami; Panama was very hot with the occasional rain shower; New York was freezing cold and had snow on the ground!

Palm trees in wind on the beach, Hollywood-by-the-Sea
Warm but extremely windy in Miami…
Empty beach on an island off Boca Chica, Panama
…Beautifully hot and sunny in Panama…
Snow on the ground in Central Park, New York
…Freezing cold with snow on the ground in New York!

For more information about this trip click here to read How to Combine Miami, Panama & New York in One Epic Trip.

National/Religious/School Holidays

These types of holidays can always have an impact on a trip, but they become important considerations for a multi-country itinerary.  They can affect how popular a destination is at the time of year you are planning for.  This in turn can affect the cost of travel and accommodation.  For example, when we planned our Hong Kong-Japan-China trip our initial itinerary meant that we were due to land in China on the day before Chinese New Year.  As this is a very popular time to travel the cost of flights was high.  We therefore decided to spend an extra day in Japan and landed in China the following day.

It is also wise to bear in mind that the same event can have a bigger impact in some countries than others.  For example, if you are travelling to countries with a Muslim population during Ramadan you may find a difference in the way it is observed.  This in turn may affect your trip.  For example, due to airline routes a popular multi-country itinerary is to travel via the United Arab Emirates to an Indian Ocean destination.  If you were thinking of a Dubai and Mauritius multi-country itinerary consider the following: in Dubai, where Islam is the main and official religion, the Visit Dubai website says this about the observance of Ramadan:

Eating, drinking (including water), smoking and listening to music are not allowed in public during the daylight hours between sunrise and sunset. However, a number of dining spots remain open and discreetly serve food to non-Muslims, particularly in shopping malls and hotels, as well as a handful of independent eateries. These venues are curtained off and obstructed from public view.

There is a Muslim population in Mauritius but restaurants remain open and eating and drinking in public is not affected.  The difference in observance does not mean you should rule out such an itinerary. However, when planning a trip it is clearly necessary that you are aware of the difference. 

These examples illustrate the importance of researching what is happening in your intended destinations at the time of year you plan to travel.

We have written articles to help you decide when the best time is to visit the following countries:

3. Plan how to travel between countries

The mode of transport you use between countries will largely depend on three factors: transport availability, cost, and time available.


A geography question for you: which six countries in the world do not have airports? (See the end of section 3 for the answer)

The question above demonstrates that flying between countries is a global method of transport, perfect for a multi-country itinerary.  However, if you don’t like flying then countries like Iceland, Mauritius, and New Zealand will be off limits unless you’re prepared to research and use the very limited sailing options, or go on a cruise ship.  

If you have a country that you’re desperate to see and you want to combine it with another, researching the flights going in and out of that country is a great way to get ideas for a multi country itinerary.

Flying an indirect route can open up stopover options.  This is a great way to boost a multi-country itinerary.  For example, when we planned our Winter Park ski trip we made the most of Icelandair’s fantastic free Iceland stopover.  Without affecting the price of the air fare, Icelandair will allow you to spend up to seven nights in Iceland when you fly across the Atlantic (between North America and Europe).  Our ski trip turned into a multi-country itinerary as we were able to combine a trip to Iceland with skiing in Colorado.  We did this using the London Heathrow to Denver International via Reykjavik route.  Emirates, Air Canada, Finnair, and TAP Portugal, amongst others, offer something similar in their home countries. Our favourite online resource to help research flight routes is

Red Arrows taking off from Bournemouth Airport
If only travelling by fast jet was an option for those of us who are not Red Arrows pilots

Alternatives to Flying

Flying, however, can be expensive and, once you’ve factored in the time spent getting to, from, and at the airport, it is not necessarily the most efficient option.  Additionally, whilst you can fly into pretty much every country in the world, you may not land anywhere near where you want to be.  It is, therefore, well worth researching other methods of transport as some of the options may surprise you.  For example, if you want to do a Baltic trip and visit the capitals of Finland and Estonia the best way is via ferry.  Whilst you can fly between Helsinki and Tallinn, the ferry is both quicker and cheaper.  Or you may wish to take the high-speed ferry between Algeciras in Spain and Tangier in Morocco as an alternative to flying between the countries.  

Travelling by train, particularly for a European multi-country itinerary, can be much better than flying.  The European rail network is vast, you can get to pretty much anywhere on the continent, and ticket prices are reasonable (excluding the UK).  The two vital planning resources are and We cannot recommend these highly enough.  The rail network in the USA and Canada is also fantastic for a multi-country/state itinerary. We love travelling by train as you get to see so much more. The same goes for travelling by bus. 

Amtrak train pulling into Winter Park station, Colorado
The American rail network is fantastic for a multi-state itinerary

Driving is, of course, another option.  However, some countries are better for road trips than others and you must be well-versed in each country’s driving legalities (see below).  Not forgetting that there are some countries where you’d need to be crazy/extremely brave to get behind the wheel!  With the right itinerary, a road trip makes the perfect multi-country itinerary.  Particularly if you are able to share the driving and/or the distances between places are not too great.  The freedom and flexibility that driving can give you can mean that you see and do more than you otherwise would.  Although the trade-off is that it may not be the most relaxing holiday.

Answer to the geography question: the six countries without airports are Andorra, Liechtenstein, San Marino, Monaco, The Vatican, and Palestine (NB. there is disagreement over whether Palestine is an independent country or not).

4. Know what the visa/entry requirements are for each country on your itinerary

Imagine devising the perfect trip.  One that you spent ages looking forward to as it takes you to countries you’ve been desperate to visit.  The trip is going to plan and you’re having a fantastic time.  How awful would it be for the trip to be ruined because you have overlooked the entry requirements for one of the countries on the itinerary?

The entry requirements which apply to you are dependent on the passport you hold and how long you intend to remain in the country for.  Entry requirements can be complicated and there are some visas which allow you to travel to multiple countries: visiting countries within the Schengen Area is a prime example of this.

You should research and apply for any necessary visas in advance before booking any travel.  This isn’t always practical, however, especially if you are concerned about things such as flights being sold out or the prices increasing as visas are only valid for a limited period.  We have certainly been guilty of booking flights and accommodation before visas to secure a good deal.  It is clearly a risk, particularly if you have paid for the cheaper, but not necessarily cheap, non-refundable options.

Transiting Through a Country

It is stating the obvious to say that if you know you cannot comply with a country’s entry requirements you should not include it in your multi-country itinerary.  What is less obvious, however, is ensuring you are aware of any requirements for countries you are transiting through.  An example will illustrate the point:  

A US legal question for you: you hold a UK passport and are travelling on an Air New Zealand flight to Auckland.  It is an indirect flight with a 2 hour stop at Los Angeles International airport, just about long enough to stretch your legs in the airport.  Do you need to be concerned about US entry requirements?

The answer is yes!  The US has a strict visa policy which applies even if you are transiting through the country and not leaving the airport. Some countries are part of the Visa Waiver Program (the UK is one such country) but people from these countries need to have a valid ESTA (Electronic System for Travel Authorization) issued before arrival.  So, in the above example, whilst as a UK passport holder you do not need a visa to enter New Zealand (i.e. the final destination) you need an ESTA to travel through the US.

The important thing to remember is to properly research the visa/entry requirements for the countries you wish to include in your itinerary.  This includes any countries you intend to transit through.

5. Research the currencies you will need

You won’t get very far in any country without money.  Whilst a lot of countries accept credit/debit card payments, there are others in which paying by cash is ubiquitous.  In any event, you will inevitably need cash for tipping and such like.  In our view, it is unwise to rely on using an ATM in each country.  What will you do if you can’t find one?  Or what if the one you have found isn’t working?  Whenever possible, for most countries it is sensible to take some of the local currency with you, enough to last for the first few days in case you encounter difficulties.  

Multi-country itineraries provide an added complication when it comes to currency if the countries you are visiting have different currencies.  For example, when we visited Iceland en route to skiing in Colorado we needed Icelandic krónas and US dollars.  Neither country accepted the other’s currency and we didn’t want to rely on getting cash when we got to each place, not least because we were arriving late in the evening each time and had other things to sort out without worrying about cash.  We ensured that we took some of each currency with us, at least enough to get through the first few days in each country.

In contrast, when we combined Miami and New York with Panama we were able to use US dollars everywhere. We discovered in advance that the Panamanian balboa is tied to the US dollar, one dollar equalling one balboa. US dollars are legal tender in Panama and so we only took dollars with us.

Our trip to Croatia, Italy, and Slovenia was somewhere in between the two examples above.  All three countries are within the EU and we assumed the Euro was the official currency of them all.  As a result of not researching properly we landed in Croatia only to find that we needed the Croatian kuna.  Whilst the Euro is accepted in some places, you can’t get very far without kunas.  In addition, in Rovinj (our first stop) very few places accepted credit/debit card. We found this out for the first time when we tried to pay a restaurant bill.  We were embarrassed when neither Euros nor plastic were accepted!  Luckily there was an ATM across the road from our hotel so we were able to get cash for the time we were out there.

For more on the Croatia/Italy/Slovenia multi-country itinerary click here 

For more on Rovinj click here.

Depending on how much cash you are carrying you may need to bear applicable declaration obligations in mind.  This is usually necessary only for large amounts (for example, the equivalent of £10,000 or more when entering the UK) and so it will only apply to certain travellers.  It is also imperative you research in advance what money you can and can’t take in and out of a country.  For example, it is illegal to take the Tunisian dinar in and out of the Tunisia and the Tunisian authorities take this seriously.

6. Ensure you are aware of a country’s important legalities and customs

We have all read news reports of people being arrested whilst on holiday for inadvertently breaking the laws of a country.  You do not want to be this person.  Avoid this happening to you by ensuring that you are aware of a country’s important legalities and customs.  It is particularly important for a multi-country itinerary because what might be acceptable in one country may not be in another.  The three categories we think are always relevant are: alcohol limit, driving, religion/tolerance, banned substances.

Alcohol Limit

Do you intend to drink alcohol on you holiday?  Do you intend to drive on you holiday?  If you answered ‘yes’ to the first question you need to know what the age limits are for drinking alcohol (this is particularly important if you are under 25).  If you also answered ‘yes’ to the second question you need to know what the legal limits are for driving.

To give you an example, our first experience of the USA was on a multi-state trip taking in California, Nevada, and Arizona.  The legal age for drinking alcohol in California and Nevada is 21 whereas in Arizona it is 19.  This wasn’t a problem for us (being well-beyond 21 on this trip!) but the difference may catch you out if you’re not as old as us!  In all three the alcohol legal limit for driving is 0.08%, the same as the UK

In contrast, when we did a road trip from the UK through France to Belgium we had to be mindful of the differences. In France and Belgium the alcohol limit is 0.05%, less than the UK‘s limit of 0.08%.

Be particularly wary of drinking alcohol on the plane and then picking up a hire car.  And be wary of having a big night out and driving the following morning.  You may have more alcohol in your system than the legal limit allows you to drive with.

Enjoying cocktails on the banks of the river in Ljubljana
Don’t get caught out by alcohol – these are a great non-alcohol alternative


Driving on a multi-country itinerary is a great way to travel from place to place and/or to see individual destinations in more detail. However, the applicable laws and rules can vary and it is extremely important that you are aware of them. In particular you should research:

  • how old you need to be to drive/hire a car,
  • whether you can drive using you own driving licence or whether you need an international driving permit,
  • insurance requirements,
  • what side of the road you drive on,
  • whether you need to carry additional equipment, for example, reflective jackets, alcohol testing kits, warning triangle etc,
  • speed limits, and whether having a device alerting you to traffic enforcement cameras is legal,
  • other rules, such as, who has priority, what to do on a red light, travelling with children etc.
Bronze Kia Picanto - Barbados Hire Car
The bronze Kia Picanto. Thank you Barbados for our favourite hire car to date! BRONZE!


When in another country a good traveller will be respectful of the local customs and traditions.  On a multi-country itinerary these may vary from place to place.  What is acceptable in the first country may not be so in the second.  A lot will depend on how liberal or conservative the country.  Researching in advance will ensure you do not cause offence, or worse, in each country you visit.  In particular you should look at the countries’ attitudes towards:

  • what to wear in public,
  • LGBTQ,
  • solo travellers (especially solo female travellers),
  • couples travelling together if not married.

Banned Substances

Clearly don’t travel with substances that are obviously illegal, heroin, cocaine etc.  You don’t need us to tell you that and that isn’t the point of this section.  The point is to remind you to check what is banned in each country on your itinerary so you don’t inadvertently travel with something that you shouldn’t.  What may be completely innocuous in country A could get you into trouble in country B.  For example, don’t travel with: chewing gum to Singapore (unless medicated or dental), Vicks inhaler or Sudafed to Japan (they contain pseudoephedrine which is banned), or cigarettes or pro-religious literature to Sri Lanka.  

7. Vaccinations

Check the vaccination requirements for all of the countries on your intended itinerary.  Let’s use Cape Verde as an example.  If you are travelling from the UK the recommended vaccines are hepatitis A, tetanus, and typhoid.  The majority of flights are indirect and so Cape Verde is a good place to include on a multi-country itinerary.  One of the main hub airports for the islands is in Accra, the capital of Ghana.  A pretty cool multi-country itinerary would be the UK to Ghana to Cape Verde.  However, yellow fever is a recommended vaccination for Ghana so you would need to add that to the list.  Even if you decide not to include Ghana as a proper stop and transit through instead, if the stop is for more than 12 hours (even if you don’t leave the airport) you will still need to have the yellow fever vaccine before flying on to Cape Verde.

The green vista at Cape Coast, Ghana
Cape Coast, Ghana. Check the vaccine requirements when adding to a multi-country itinerary

8. Travel insurance

Make sure your travel insurance covers you for all countries on your itinerary and activities you intend to do.  Depending on the provider you may be able to use single trip insurance even though you are going to more than one country.  Check the policy carefully.  Remember, you may need to pay a little more for multi-country insurance.

Skiing is a great activity to include in a multi-country itinerary but winter sports usually need to be added to a policy.  When we did a multi-state trip to California, Nevada, and Arizona we skied at Lake Tahoe for a few days.  We had to ensure our insurance included skiing, even though it was only a few days in a much longer trip.  The same applied when we skied in Japan on a Hong Kong-Japan-China multi-country itinerary.

For ideas of great ski destinations to include in a multi-country itinerary click here.

Falling in love with skiing at Nozawa Onsen - view from a slope
Make sure your insurance covers you for all countries and activities on you multi-country itinerary

9. Make sure you know if there is any time difference between the countries you’re visiting

Time differences can be a pain at the best of times, especially when the difference means you’re going to have to deal with jet lag.  Knowing what the time difference is between the countries you’re travelling to is important on a multi-country itinerary.  For example, if your travel depends on you making flights you don’t want to be working to the wrong country’s time.  The same goes for any plans you make that are crucially dependent on you being on time.

10. Check whether there are differences in electrical voltage/AC adaptors between the countries you’re visiting

This sounds like such a small thing until you come to plug your hair straighteners in and you find that they worked perfectly well in Iceland but not in the US due to the voltage difference! 

These 10 tips should help you plan a brilliant multi-country itinerary. You will see that a lot of the tips are also very helpful for single destination holidays. However, the issues become more acute when you add further countries/states to your itinerary and using the tips becomes even more important.

We’d love to hear about any multi-country holidays you’ve been on or are planning! Tell us about them in the comments section below.

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