The short answer to this is I plan it first for myself, then I add little bits and pieces of itinerary to cater to the diverse interest groups.
There are, however, some pre-conditions that need to be met:
1. Stick to a budget that everyone (I am) is comfortable with. That means most of our trips will be centred on Southeast Asia (which I personally like), with short-haul flights (yes!).
2. The holidays are for the kids. There is a common understanding within the family that when the kids enjoy, the adults will too, and we can trust ourselves to entertain ourselves.
3. The trips are more about spending quality time together, and about character-building. We try to cut out the frills and luxuries (we allow ourselves to cheat a little once in a while). In my opinion, what better way to achieve that than to rough it out in the jungles or mountains.
Actually, I added number 3 myself. However, since I have always been the organiser, I think I have every right to pursue my own agenda. The reason why I have been the organiser had its roots in me being a former Malaysian citizen. Our first overseas trip was a road trip to the organic rice farm in Kahang, Johor. Since I was born in JB, the responsibility of putting together this trip just fell on my shoulders. I think the successful reception of the maiden trip bolstered the family members' confidence in me. And hence the birth of the Wong's Travel Agency.
After adhering to the three pre-conditions, I would consider the specific needs of the various groups of people.....which basically, are the mothers. There is a common understanding within the fathers/brothers-in-law that when the wives enjoy, we will too, and we can entertain ourselves.
My wife has five elder sisters and a sister-in-law who is a regular on the tour circuit. They grew up in kampungs and anywhere or any activities that can bring back fond memories of those days will win them over. To sell them a suspiciously "hardship trip", all I needed to do was to include some appealing key phrases like : fruit farm, vegetables and fruit market, shopping for produce etc.
By adopting this strategy, we managed to experience the majestic beauty of Mount Bromo, the cool air of Batu and the unbeatable fun at Batu Secret Zoo; visited more volcanoes and hot springs and tea plantation in Bandung; took one of the last few KTM train journeys to a town in Pahang and spent Christmas morning munching away in a market in Temerloh; and observe semi-wild orang-utans up close in Leuser National park, and river-tubing in Bukit Lawang; and of course the most recent trip to Khao Yai in Thailand.
All these sound fun, but not many people know that it is actually a very stressful and thankless job to be responsible for the well-being and happiness of a "village". It was a first time for me too to all those places, and God knows if reality tallied with the research done online and in books. I had to live and die by the decisions and choices I made.
For example, the bungalows I booked for Bukit Lawang trip received very good reviews. I did not pay much attention to the few comments by travelers on the steep climb up the hill to reach them. How bad can it be, I thought. Boy was it bad for the aunties when they wanted to give up and change bungalows half way up the hill. A ten-km trek through Khao Yai National Park to spot wildlife? We had to call our drivers to help pick us up at the halfway mark.
These are part and parcel of adventure travel, even though they did not really sign up for an adventure package. However, these were also the stories that kept being repeated at dinner tables, (painful) memories that reminded the aunties about our mortality, even though I have received strict directives on what NOT to do on our next trip.
I am glad my children are blessed with a lovely extended family, and having the chance to grow up with so many cousins. Until the day the family decided to swap agency, I will continue to plan these trips, regardless if they make a profit or not, so that I can continue to gift them such memories.