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A Guide to Planning and Enjoying a Multi-generation Family Holiday

Travelling in a large group of friends and family, to the hills of Himachal or Uttarkhand was the only way we travelled while growing up. I have memories of those road trips, stretching over a couple of days, when we packed food for the road, still made frequent pit stops at local dhabas on the highway, were never in a rush to reach our destination, but once we did, we all settled in quickly. The parents were happy to have all the kids off their chest, and us kids would be thrilled to spend our days playing games and running around, and well, just being kids. Our demands and needs were much simpler and adjustments and joy came fairly easily.

Today, most of us are city dwellers with fast lives and jobs and commitments, and while we are travelling much more than the generation before, most of us chose to do it with our partners or a small close knit group of friends and family. In fact, the more I think about this, I realize how immensely our travel habits have changed from childhood to adulthood,  with a much greater focus on individual experiences and enrichment, that fulfil our desires for exposure and personal growth. In fact, I ran an Instagram and Facebook poll asking if people would consider travelling in a large family group and the majority on both platforms had concerns and felt that they would lose their mind 🙂 . In addition, changing lifestyles, challenging logistics and time all add up making large group travel almost non-existent in the modern family unit.

Over the last couple of years, I have had the opportunity to travel in an extended family group, on my husband’s side, and I have been surprised that I enjoyed these travels as much as I did. I have always loved to travel in a small group of friends or with my partner, where I take the charge of leading the itinerary, and I have a lot of control over what I end up doing. I also like a bit of space and doing my own thing, so I wasn’t sure if I would every fit in with a very large group of family travelling together. It sure was a different way of travel for me, but different isn’t necessarily bad. In my experience, there is one main qualifier that tilts the balance in favour of this style of traveling.

Quality time.

When you live in a city, whether you are single or married, have kids or don’t, spending time with your own family and siblings can get difficult, and extended family, rarer. A holiday together can allow for all sorts of memories, and even if they are weird, funny incidents, they make for a good story for later. And from a personal standpoint, travelling with multiple generations can throw up interesting experiences that you maybe have never even considered otherwise.

If you are considering a trip with parents and aunts and uncles and cousins, here are my top tips to help you play an Effective Organizer –

Fix the Budget

This should be the starting point for any group holiday. And it’s also a tricky one, as not everybody is comfortable discussing budget openly. It needs some tact and insight to narrow a budget per person that is realistic and comfortable for each family and then get everybody’s agreement on it. You may want to have a one on one discussion with some members but this is one of the most critical pieces to align initially.

Keep in mind that flights/trains, activities, extra meals, drinks will all add up. And you don’t want people disappointed when they ended up spending way more than what they wanted to. So plan well, and be very clear on what’s included and what’s additional. You have to be comfortable discussing money with the family.

Hotels will be happy to share payment links that individual families can pay directly to. Flights can be paid individually by every family as well. Any common group expenses can be done by the organizer, pre-paid or post, on the comfort of the group.

Set a date and duration

Multiple generations and agendas, job responsibilities, school breaks etc. all mean that there is a narrow window in the year that will work for everybody. Fix the time of the year that works for all, then fix the exact date and number of days. For the first trip, a good duration is 4-5 days, enough to explore a place but not too long to get restless. And any family that wants to explore further can continue their trip independently post the holiday.


With budget and duration out of the way, you can start thinking of destination options. Again, for a first holiday, I would really recommend picking a place that is well connected and does not involve extended periods of travel on the road. Once you are on the road with a large group, everything takes longer. So pick a well-connected destination. Keep in mind the family members coming from different cities or countries and how easy or difficult it may be for them. Do the research on the visa requirements, weather, stay, activities, extra costs and line up 3 options, in order of priority and list pros and cons. Make the choice democratic and let everyone vote.

Accommodate everybody

With a group spanning three generations, it’s a fact that interests and physical abilities will vary significantly which is why you will need a destination that has a number of choices for activities. Resorts for example are a great option. So are cruises.  Facilities such as a swimming pool, walking trails or treks, kids club, shopping, local activities can keep everyone engaged. I have learnt that no matter how exciting a destination, if it does not have enough “to do” in close proximity, it will be extremely hard to keep everyone entertained.

Another important element to watch out for is the availability of a common space where everyone can get together. It could be a library or a private section of a lobby for example. This is important as the group will want a place to assemble at, at different times. Giving up your room or expecting anyone else to do it can be uncomfortable, so make sure to discuss the possibilities with the resort.

Allow for time outs

While it’s good to have a plan and activities lined out, accept that not everyone has to do everything together. Little breaks of being independent or in smaller groups are actually great for everyone to not feel restricted. In Coorg for example, we went for a rainforest walk that almost everyone in the group did (from age 3 to age 70), but there was a hike (Nishani) that a very small group decided to go for. Pushing those who don’t enjoy a harder hike OR asking some to skip it, are both are unfair and unnecessary. The idea is to spend quality time together but little time outs don’t hurt.

Fix the food

Food is an extremely important part that can make or break any holiday. In my experience, I have found it to be extremely tedious to do an ala carte menu with a large group. Ensure that a breakfast buffet is part of your package so that everybody gets their morning fix. Try and speak to your hotel for a fixed menu for other meals. If you are eating outside at another place, fix a menu and book a table. Believe me when I say that people can get very grumpy when they are hungry, and it is extremely hard for a lot of smaller restaurants to serve large groups efficiently, unless pre-planned. Food is one area that you should not leave open for any spontaneous decisions. Make sure to pick the right places that cater to popular tastes and also include local food in your plan. And if few people want to have some adventure with food, allow scope for them to do that independently.

Make evenings about a fun activity for everyone

Evenings are the best time for everyone to get together and spend time together after a day of activity. Make sure to line up interesting things that can be done in a group – for example games (our group loved Mafia and it has now become a staple at every family holiday), playing music, singing songs or just catching up on family gossip. Evenings are a great time to wind down and bond and draw a list of games or activities that can be enjoyed across generations.

A souvenir or memento

This one is of course not necessary but if the budget allows, as the organizer its great fun to source a small memento that everyone can carry back. A t-shirt, a group photo, a local souvenir all are appreciated. It’s really not about the value but the thought and memory.

With the practical tips out of the way, I also wanted to share some behaviour learnings I had, that go a long way in keeping the holiday fun and breezy. These are important for you as an organizer, but also for others in the group and your own attitude can help set the stage for everyone’s temperament.

Keep an open mind

You don’t think it’s really fun to go see a museum, but the cousin’s kids insist and you moan and complain and then put your grumpiest face on. Don’t do it. Part of the fun is to keep an open mind and do things that are not “you”. There is a fair chance that you will hate it; there is a very fair chance you won’t.

Get to know your family better

Quality time with family is rare and treasured. This is a great occasion to spend hours chatting and catching up, with no distractions. Make the most of it.

Take time out when you need it

If you need a break, take some time out. Chill in your room, or go for a walk or read a book. I am a firm believer of taking one’s space and returning back rejuvenated.

Don’t take things personally

Spending so much time together in such close quarters can trigger arguments or differences of opinion on the most trivial things. The reality is that when you are on a holiday together, you can’t walk away and leave. Sulking beyond a limit in unpleasant for everyone. So if things are said, letting it go and not making a personal deal out of it are important.

As an organizer specially, if people are not in agreement to your choices, don’t take it personally. Accept and move on.

Your opinion on every matter is not important

With so many people across generations and ideologies, there are bound to be some differences in opinion on matters big and small. How the cousin brother parents his kids and your own views on it are not really relevant to be stated out aloud. (Indian)Families can tend to be very opinionated on matters of parenting, drinking, sleeping, eating, basically everything and anything 😀 . Know that it’s not necessary to give out opinions on every matter, especially avoid trivial things that aren’t a real personal bother to you.

You don’t need to please

As an organizer, you should know that not everyone can be perfectly happy with every situation. Accept that some people will enjoy certain things and others won’t. While you want everybody to have a memorable time and laud you for your effort and skills, constantly trying to please can be a major dampener on your own experience and a strain you don’t want. So kick back and chill.

Go with the flow and spread good cheer

In large groups, not everything can go to plan every single hour of every single day. Some kid will cry, someone may not feel well, someone may feel too energetic. Plans will need to evolve to accommodate all of this. Don’t get too hung up on the “itinerary”, allow room for change, and when things don’t go according to plan, just smile and move on. Remember, there is nothing better than the one cheerful family member amongst a sea of chaos.

I hope this helps you planning a fun and exciting trip with extended family. It will be different for sure, but it will be worth it.



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