In Travel on Friday 4th Aug, 2017

How to travel with friends: 5 tips for a really great time

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At its best, travelling with friends, a best pal or a small group enriches the shared life experiences and the compatibility that brought you together in the first place. Whether it’s an organised tour or your own planning with an agreed-upon itinerary, it’s an exciting experience to embark on together.

But living together 24/7, even in the short term, can reveal surprises and stresses not evident in day-to-day interactions with your nearest and dearest. The following are some tips to help set expectations and ensure your holiday is indeed the wonderful memory your friendship deserves.

1. Understand one another’s daily habits

Because we know the devil’s in the details …

  • Are you an early bird to her night owl? After a long day of sight-seeing, a hot bath and bed is the only solution for some. Others read or watch TV or engage with locals and other guests – the wind-down process for people can be very different.
  • Timeliness: Do you agree that breakfast is at eight but know it’s impossible for the group to gather before nine? Is an appointed time only a suggestion? It’s hell to wait, and the stress can go from annoying to unbearable pretty quickly. Be advised.


  • Are you wash and wear traveller paired with a fashion plate? 
  • If meals are important to you, are you okay with someone who grazes all day?


  • Here’s a big one, and a sensitive one: drinking. Wine at lunch and dinner may be outside your purview at home, but your companion/s may see it as part of the cultural experience and a luxury of the holiday. Give some leeway here; it’s okay to do the afternoon’s museum on your own. 

Read more: Making friends on holiday is easy with these simple tips

2. Know the travel tics and priorities

  • Are you traveling with a compulsive (phone) photographer? It’s hard work being around a photo-hound, according to my friend. She’s the one grasping the iPhone, always looking for the right angle, composition, and lighting, taking multiple shots. If you’re guilty, share your work as soon as possible with flattering shots of your pals, or better yet, ask someone to snap all of you. It’s like an immediate post-card everyone can forward.


  • The structured versus the spontaneous. Are you a deep-dive, paired with a drive-by? Are you carpe diem to her scheduled itinerary, unruffled by ‘getting lost’  for the thrill of what you might discover? A meeting of the minds is due here, with some concessions to be made on both sides. Lots can and will happen on the fly, so stay flexible.
  • Is shopping a must? Tourist trinkets, serious purchases or exotic markets?


Some of us can’t pass up a shop; for others, it’s simply not as important as soaking up the experience. Know before you go which side of the ledger you and your pal fall on so you can adjust the expectations accordingly.


Maybe you linger at the museum exhibits while your pal/s explore the market.

3. Manage expenses on the road 


  • Agree beforehand how shared daily expenses will be allocated. Trip kitty? Keep a tally and settle at the end?
  • Split a joint bill with cards where possible. I don’t mean down to the last cappuccino, but a pay-as-you-go plan avoids sticker shock at the end and helps the budget-minded keep track of their spending.
  •  Disposable spending is often a sensitive topic; be mindful and considerate.

Read more: What to do if you arrive at the wrong airport

4. Consider your own room

  • Sharing accommodation can be fun and certainly cuts down on expenses. But, with multiple destinations, a night or two on your own will give you both some welcome privacy. 
  • If you’ve committed to sharing (a cruise or tour), arrange some alone time in the room to give each of you a privacy break.
  • In shared quarters, be über-vigilant about neatness, particularly in the bathroom! 

5. Mix it up 

  • Have a cousin in a town you’re visiting? A long-lost college roommate?


Some of the best experiences I’ve had travelling with friends is to meet their friends along the way. If you’re lucky, you’ll come away with a new friend yourself, but even if it’s just a passing afternoon it will be one of the sweetest memories of the trip, I promise. 

In closing – a few rules of engagement

  • Every few days, take a few hours off from each other’s company to follow your own bliss. Don’t feel you have to do everything in lockstep. Afterward, sharing the solo adventures is like hitting the refresh button on the day.  
  • Be considerate in your social media posts – pictures that are hilarious between the two of you may not be as funny once posted on Facebook.
  • Communicate. Don’t let pent-up irritation ruin even a moment. If there’s an issue, get it out there. That’s what friends are for. 


I feel so very lucky to have had the privilege of deepening my friendships through travel. Friends who endured my tics with humor, patience, and grace.  I hope I returned the favour in some way.

This is certainly not an exhaustive list. What are your experiences and the lessons you’ve learned through travelling with friends? Please add in the comments below!

Jane Trombley is founder of 3 Score & More, a blog launched to inspire travel and discovery among curious women 60+. As part of the ‘three score and more’ demographic, she is no stranger to life’s reset button. After careers in advertising, communication, and a very rewarding stint in adventure travel, she is following her heart and encouraging others to do the same. Jane is based in the Hudson Valley, New York, USA.

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