So you want to gather your loved ones for an overseas trip, but the thought of planning and executing it daunts you? We feel you – planning a holiday is a stressful event in itself. There’s not only the logistics of buying plane tickets and accommodation, but also deciding on itineraries and budgets. Add kids and grandparents to the mix, and it seems like a recipe for conflict and stress.

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In fact, half of Singaporeans waste four days of leave every year because of poor planning, according to a regional 2017 survey conducted by Beringer Vineyards, who also found out that four out of five people find trip planning more fun when it’s social (and over a glass of wine). The good news is, there are ways to make planning for a multi-generational overseas trip more fun and less stressful, so everyone from six-year-old Chloe to seventy-year-old grandpa Sam will have the best time ever.
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Here are eight tips to plan a successful and enjoyable family vacation:
It’s often said that you don’t truly know someone until you travel with them, even family members. Do you prefer café hopping or wine tasting? Would you rather spend all day sightseeing or learning something new? We all have a different style and understanding everyone’s before you leave will help you know what to expect. You can also raise any potential issues before they build up, helping to lessen the chances of conflict during. With good communication, consideration and a little bit of patience, your family vacation can end up being one of your favourite trips ever!
Budget can be one of the main causes of tension on a group trip, and even more so when it comes to family. That’s why it’s absolutely important to set one beforehand. Be honest with both yourself and your family on how much you’re willing to spend. Discuss how your group will split costs, and if you decide to have a group budget, exactly what shared costs it will be used for (eg. accomodation, transport etc.). Apps like Moneyboard, a personal finance App, can help keep track of your trip expenses too.
Even the best laid plans don’t always pan out, and planning every day of your vacation can set you up for disappointment. Instead, decide as your group what your priorities are – pick things that truly excite you and the group, and not just what’s trending. Try and cover a range of priorities, from activities and attractions to restaurants and the latest winebars. Don’t forget to check for opening and days and times! If you can’t fit everyone’s priorities in, consider splitting up and then regrouping at the end of the day to share stories.
Expecting to plan every aspect of your trip in one night can make your planning session more stressful than it needs to be. Instead, cover all the important parts (like the ones listed above) and then get different family members to take charge of separate aspects of the trip. Pro-tip: Use collaborative Apps such as Google Maps and Google Sheets.
The last thing you want when booking your hotel, AirBnb or flight tickets is to discover that they’re full or unavailable. The benefits of planning and booking important things like this in advance cannot be overstated, and will save you the stress of scouring the internet for something last-minute, which may not be the most ideal choice for your group. The earlier you book, the better deals you may be able to find as well.
If it’s the first time you and your kids are travelling with grandparents (or other kin), they may not be used to having to wait for others or having your attention divided between them and other members of the family. Speak with them before the trip and explain to them the importance of compromise and considering other people’s needs when travelling in a bigger group.
A big family vacation like this probably only happens once in a blue moon. And since you’ve poured so much time and effort into planning the trip, don’t let any good photo opportunities go to waste. Bring along a portable camera, or even an instant one like the new Fujifilm instax Square SQ20 or the LG Pocket Photo Snap (which make great gifts too!) and snap away.
Always expect that anything can happen. Have an open mind – if you get to your destination and decide you want to deviate from your itinerary, go for it. It is also important to get travel insurance. Whether it’s a flight delay, theft or an illness on your trip, insurance will protect you and your close ones, and could save you a ton of money.
Most importantly, have fun with it. Travelling opens up a world of possibilities and this can begin from the moment you start planning it. Grab your family members together and start thinking about all the new experiences and memories you’ll be creating.
Plus, with these tricks up your sleeve, your next travel planning session is bound to be a breeze and you’ll find the excitement of making plans just as exciting as the actual trip!
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Tips provided by Beringer Vineyards / Additional reporting: Elizabeth Liew