Multi-generational holidays are on the rise which probably isn’t surprising when you consider our hectic pace of life. After all, when else do we get to spend real quality time with our favourite people?
But living in close proximity to other people, however much you love them, can be fraught with difficulties. On the other hand, if you plan carefully, your holiday could deliver some truly amazing memories. Here are a few things to consider both before you book and during your holiday.
Hotel or Self-Cater?
A hotel holiday is often perceived as the most relaxing option and, when it comes to large groups, possibly preferable if you want a little more separation from the rest of the group. Staying in a hotel means you’ll naturally avoid any negotiations over who’s responsible for the everyday chores of shopping and cooking, plus retreating to your room is easier in a hotel than a villa.

However, checking into a large luxury villa will undoubtedly give you far better value for money and, with some thorough research and clear parameters, can provide just as much freedom. But best of all, staying in a villa means you get to do the simple but memorable things together, whether catching up with a friend or daughter’s latest news while you prepare lunch or enjoying a precious game of table tennis or table football with a grandchild.
When Is the Best Time to Book?
There’s no question that the sooner you book the better, particularly if you’re limited by school holidays. With any large party, you’ll be juggling a whole range of requirements, from holiday dates to the number of bedrooms.
The best luxury villa rentals in Sicily and in the Mediterranean, particularly those with a pool or by the sea, invariably get snapped up quickly for the months of July and August. Book as soon as you can agree on dates, and you’ll get the best choice of accommodation and also the best value flights.
Agree on Budgets
It’s so important to have an open discussion at the outset about who’s paying for what. You may feel that a multi-gen holiday is a wonderful way to treat your children and grandchildren, but there’s no need to pay for the whole lot! You’ll need to discuss who’s paying for flights and accommodation before you book anything. To avoid any unpleasant surprises, a frank conversation about meals and activities is a good idea before you go.
What Are the Main Pitfalls When Choosing a Holiday Villa?
I always advise guests to sort out the items which are non-negotiable first. A villa with a pool is often the number one priority, or proximity to the beach or town. Next come bedrooms and bathrooms. You’ll need to work out who’s prepared to share and whether you want an ensuite bathroom for each bedroom. Consider also the age of any children in the group and whether extra facilities such as games or a hangout space for them, either inside or out, would be a bonus.

And last, but definitely not least, think of yourself! If your group includes several younger families, would you prefer to be slightly separate from them? If so, choose a villa with an independent annex, and even a private terrace and kitchen, which will give you an escape route when it all gets a bit much!
Is It Better to Be in Town or on the Beach?
Choosing your location will be very personal. A group with babies or young children may prefer a beachfront location to avoid having to pile everything into the car for a hasty hour on the beach. Teenagers, on the other hand, may want to be able to walk into town for a pizza or ice cream on their own. And, of course, if you’re all arriving on different days, think also about how far you want to be from the airport.
Freedom to Do Your Own Thing
A lack of freedom and feeling compelled to do things that simply don’t interest you can be one of the main reasons that group holidays break down. Having separate cars means you can allow for splinter groups: while an afternoon in town may be your idea of hell, teenagers may prefer shops to another set of Greek ruins. Also, establish babysitting rules before you go so that you’re not left dealing with toddler tantrums too often while everyone else is out having fun!

Compromise is key. The holiday pace is likely to be considerably slower if there are babies and toddlers involved, and the perfect holiday is one where everyone moves at their own pace.
How to Organise Everyday Chores
Squabbling – or worse still, suppressed irritation – because someone’s not pulling their weight is disastrous for any multi-gen holiday. If you’re self-catering, keep a list of shopping requirements so that anyone going near the shops can stock up on provisions. And on the days that you eat in, stick to communal eating. After all, getting together round the table with delicious food is one of life’s great pleasures! Prepare, eat and clear up together and encourage children to play their part, even if only in setting and clearing the table.
But a holiday is also a chance to awaken your taste buds so be sure to include at least a couple of meals out. And even if your holiday isn’t marking a special celebration or milestone, booking a local chef to cook for you at least once is a brilliant way to celebrate the simple joy of being together.
Also read, Which Are the Best Mediterranean Islands for a Walking Holiday?
Let’s Have a Conversation:
Have you ever taken a multi-gen holiday with family or friends? Where did you go? Do you have any tips you’d like to share?