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The Secrets to a Happy Holiday with Friends

26th August, 2018

At TYW we are committed to providing independent travellers 45 years+ with the tools they need to have an extraordinary holiday.

We are constantly asked whether travelling with friends is a good idea. And we know from our clients who travel with friends there are stories of great highs and tremendous lows.

Planning a holiday with friends this September I decided to tap into the collective wisdom of our travellers and unpack the secrets of travelling with a friend – and staying friends.

Here’s what I found:

1. Know yourself

Just because someone is your friend does not mean you are compatible. And the daft thing is you can be polar opposites and still travel successfully together to far flung exotic locations. Knowing yourself and what sort of traveller you are is one of the keys. Are you like ‘go go go ‘on holiday?  Do you like to explore a big city on foot or to limit yourself to one museum a day? The bottom line is, can you compromise, let go of some of your preferences to fit in with someone else?  Can you give someone the space they need to do exactly what they want – at least some of the time? If yes is your answer, read on.

2. Speak up and manage expectations

There is an old adage, ‘to each their own’, and to travel well together you need to figure out whether your expectations are compatible. It really comes down to working out how similar or different your expectations are. Spell out to each other the purpose of the holiday and how you like to travel so you can eliminate some of the surprises and see whether there is enough common ground to go forward and each have the holiday of your dreams. One thing to really explore is how many nights you each like in one place, that can often be the deal breaker.

3. Plan ahead, but not too much

Spontaneity may sound like fun, in reality it can mean some are sulking because they want to go see the Vatican and others are fuming because they can’t see why everyone is so irritable about shopping. Just remember if everything is planned from dawn to dusk there isn’t much chance to discover things along the way. Try for a middle ground between being the ‘plan queen’ or a rhapsodically knave.

4. Build in personal space

Just because you are travelling together does not mean you have to be joined at the hip. Everyone needs ‘me time’ whether it’s about quiet time at the end of the day to relax as you each choose or spending a few days apart every now and then. It’s up to you to speak up about your needs.

5. Work out a budget

Money is always a sensitive subject and it probably causes more arguments above anything else. So, before you commit establish a budget and discuss how much you are prepared to spend on accommodation, food, transport – the hire car office is not the place to be sorting out whether you’re getting the open topped BMW or the compact Toyota Corolla. Creating a group kitty that everyone contributes to can save small squabbles, and shared expenses often even out over time that way. An app like Splittr makes splitting group expenses easy – and as an added bonus it’s   free and works off line.

6. Eating and Drinking is key

Surprisingly it’s easy to have a great holiday with people with different interests, be that bungie jumping, hiking or gothic cathedrals. Where compatibility falls apart is around the importance of food and drink. It just doesn’t work when someone wants Maccas and the rest, Michelin Star. True, the full discussion beforehand will set up expectations but if at all possible, ‘try before you fly’ with a weekend from home. It’ll give you all insight into any dynamics that may arise.

7. Open up

Whether you’re travelling in a pair or a group, travelling is a great opportunity to meet new people and for many this is the best part. Spending time with others outside the group can also take the strain off travelling with the same people day in and out. So, make yourselves approachable, smile at others, invite them into your conversation – who knows you could just meet someone with whom you’ll stay friends for life.

And lastly, don’t lose your sense of humour. You’re on vacation – laugh at yourself and chances are you’ll all be laughing together!

We’d love to hear about your experiences of travelling with friend and what we can learn from them. Please drop me a line at


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