How to Travel with Other Families and Still Stay Friends

An INSEADers story..

“We decided to take our annual family vacation last year with three other families (close relatives), to Sri Lanka. As the custom goes, I made a very detailed itinerary for my family, and the moment I shared it on the family Whatsapp group, a stream of comments flowed wherein the planned activities did not quite fit well with every member of the family. In the end, everyone got one veto and one preference that was incorporated and we made it work with a little bit of compromise. It was important for all of us to be respectful of each others quirks while traveling as one big fat Indian family!
-Ishita Gupta, INSEAD MBA

Do you remember the days when you did not have to think twice about booking a trip with your friends during your time at INSEAD? Those weekend getaways you did on a whim because, well, you could? 

While life has changed since INSEAD, it doesn’t mean you have to stop traveling. If you are like most INSEAD families and want to travel with your kids and your friends but it all seems daunting, then read on. Our travel experts (who happen to be INSEAD alums) share their tips on how to have a great time traveling with other families, be it with close relatives or friends.

Tip 1: Choose Your Family Wisely

This seems obvious, doesn’t it? But it’s not that simple. It is important to choose a family that you and your kids are compatible with. Just because you were close back in school does not mean you will still be able to travel with them peacefully- people and priorities change. Some things to consider are whether you have the same schedule, whether your kids are the same age and can get along, and whether you enjoy doing the same things as a family.

What’s Your Dream Vacation?

Does your family prefer the mountains where hiking through nature is your perfect family activity? Or does your family prefer the beach, where sun tanning with a drink in your hand while your kids have fun building sandcastles is the dream vacation?
As you figure out whether your dream family vacation matches the other families, don’t forget to check if you have the same vacation goals! Some families look for a cultural experience while others may look for fun activities to share with their kids. Always make sure that your travel goals are aligned before you agree to go on a trip together!

Tip 2: Is Everyone Comfortable With The Budget?

While discussing money can be a sensitive issue in some cultures, it is important to be on the same page as the other family about how much you’re willing to spend. Don’t forget to factor everything from accommodation, food, transport and activities.

Do you like to stay in hotels that have a nice breakfast buffet spread, or do you prefer to cook your own breakfast in your vacation home? If you are renting a car, are you taking two vehicles or sharing a big van? In the latter case, how will you split the cost, especially if you have an unequal number of members in one family?

It is also important to discuss what kind of activities both families enjoy doing. If you are a family that likes to spend on museums and theatre, be conscious that the other family may rather spend on amusement parks. This is completely okay, and you should be comfortable parting ways during these moments. When you meet for dinner in the evening, it will leave you with something new to discuss.

Tip 3: Allocate Adult Time For Yourselves

You are after all INSEADERs… You will surely want to celebrate your vacation over drinks, and may even want to stay out late at night! You should discuss before hand and agree on things such as what time you will put your kids to bed, how long you will be able to stay out, how much (if at all) you still drink so that expectations can be made clear in the beginning and you avoid disappointments.

If you do not have a budget for a babysitter and cannot leave your kids alone at home, you may want to look at booking a stay with a pool and do an adults only pool party. In conclusion, ensure that you take out the appropriate time for each other and enjoy one another’s company.

There are many more tips and tricks on how to have a successful vacation with other families, these are just some basics to help you get started. If you are ready to travel, you must immediately start your accommodation search. Prestigious offers properties and services that are ideal for big groups, i.e large beautiful properties and services such as transport, a chef and even a babysitter on call for your kids.

Tip 4: Let Prestigious Help You

Planning a family trip is already time consuming, so planning a family trip with other families may seem especially daunting. But don’t worry, our professional team is here to help you. As INSEADers and parents ourselves, we understand your needs and we are here to make your lives easier by taking care of it all for you. Just drop us a line to let us know what you are looking for and we will do the rest.

About Prestigious

Tailor made travel, just for you.

At Prestigious, we’re your personal travel experience agency.  We tailor family vacations to meet your needs and we strive to deliver the most enjoyable and stress free travel experience. Choose from our curated selection of boutique properties in over 24 destinations around the world and let us take care of the rest for you.

To learn more, please visit our website or send your requests to

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