Best place in the world for a 3-generation holiday

[Frymetothemoon]

Age range would be 4-77. 1 older couple, 3 younger couples, 3 children (4-9)
Due to my parents selling some property we would have a fairly comfortable budget.
We live scattered all over the planet so anywhere would work.
Obviously once travel restrictions are lifted, but we need plenty of time to plan and coordinate anyway.
What family holidays have you done that were a success for everyone?
What do you think is the secret to success?

i would start by narrowing down your options to places that everyone can access relatively easily, or doesn't leave one set of people with a horrendous journey. I'm wondering if the Middle East would work for you as places like Dubai, Abu Dhabi and Qatar can often be used as stopovers or hubs for long haul flight connections. That might not be the type of holiday you'd enjoy though?
Decide if you all want to be under one roof e.g. a villa and staying together the entire time, or separate hotel rooms or smaller apartments / villas in the same complex. Having done the former with my family I'm not in a rush to do it again, too many people with too many opinions in one space!
Also, agree to have some time as your own family / couple or in smaller groups as herding all those people round all the time will get tiring and you'll need find things to do that please all of the people all of the time.
If the children are from different families then a discussion between the parents before you all arrive is worthwhile to agree things like bedtime, are the kids staying up later than normal or going to bed at their usual time. Nothing worse than the first night of a holiday and one lot get sent to bed early while the others stay up!
Or what about a cruise?

Our best was Sri Lanka, but it depends what you are looking for really.

I’d suggest a cruise too!

What sort of things is everyone into, do you want an active sort of holiday or more relaxation/beach, important to have some cultural/sightseeing sort of opportunities or would you prefer a resort? Is cuisine/food important, will you be wanting to eat out a lot or cook/self cater or a mixture? Is shopping or any other particular activity a crucial element for anyone?

We're veterans of multi-generational holidays and have enjoyed Sri Lanka, Barbados, Thailand and the South of France most over the years which have provided a good mix of all the above, our criteria are (a) some cultural stuff available without the need for huge extra travel (b) good watersports and diving - which usually means good beaches too! and (c) good food, but yours might be different. We're also very willing as a family to do multi-site holidays so e.g. fly into the capital or other large city for sightseeing and shopping etc., then transfer on to the beach or countryside for relaxation or sports etc. (sometimes different family members join for different elements), but for some people that would be an exhausting logistical nightmare so depends on your preferences.

I would say wherever you are in the world having enough space is absolutely crucial, whether that's hotel rooms or a big enough villa/house (or maybe 2 or 3 adjacent ones!), if anything over-estimate on the space you think you'll need, and not going with the expectation that all day every day will be spent together, we tend to find its best to split into groups during the day (not always the same groups every day) and then come together to eat in the evenings but then again with young children it might be better to spend a few hours all together in the mornings round the pool or similar then break off for the rest of the day?

Agree you need space for everyone and not relying on one person to cook/cater/clean for everyone.

If money isn’t an issue you can get villas with chefs.. would this be an option?

Cruise would also be great giving people their own space, and opportunities to do different activities.

We had an amazing holiday in lake como recently, we had a beautiful villa with a shred pool, there were 6 villas on the complex, something like this would work?

Luxury hotel with childcare would be a bonus…

I guess asking everyone for suggestions, their top 3/5 places and seeing if there is any common ground would be a good starting point too… then everyone feels like they have a say.

As pps - so much depends on how active or not everyone wants to be and whether you want culture/city/car/self catering or beach/water sports relax or indeed a mix.
Never thought I would but how about the Maldives if budget can stretch - so many differing types of accommodation/islands/food, amazing toddler friendly beaches, boat/snorkel/diving etc. Went before Covid and was astonished completely not what I had envisaged.
For more active/cultural how about eg Cadiz - great city beaches and brilliant small city great food, culture - a couple of apartments?

I have done a 4 generation cruise (age 2 to 88) which was a great success.
Many dining options and different cabins for different budgets/ requirements. Gym, pools, spa, library, driving range etc. on the ship and quite high adrenaline excursions when in port. There tends to be cultural trips on land and an interesting range of onboard lectures.
The child care/entertainment day and night, is exceptionally good.
In the evening; shows, nightclub, cinema, musical soirées (not for us but even ballroom dancing on some ships), comedy nights, casino and onboard pub.
The 'secret' is to do your own thing, no compromise, and you will have loads to talk about over dinner ( when you choose to dine together!)

Thanks for all your input.
The main problem is the varying physical ability and interests of the participants.
A cruise would be perfect, as far as I'm concerned, but one of the parties isn't keen. So something like a cruise on dry land.
I had thought maybe South Africa? A nice lodge with a pool and lots of animals to see?
Definitely wouldn't all want to be together all the time. Also, I've been caught out being the kitchen slave before, so having someone to cook would be a definite yes from me.
Lots to think about. Thanks again for you insight.

Big villa with staff in South of France or Italy.
Safari and wine tour in South Africa - depends how fit the olds are.

Also if you have another family you are friends with across the generations then it can be fun to invite them and get a really massive house. Dilutes any family tensions and means larger groups for different types of activities

@Ooodlesofboodles your villa suggestion is proving the most popular.

Thanks to everyone though as you've given good suggestions, especially about possible pitfalls

How are your multi generations going to be with weather?

Having done safari in South Africa, it involved getting up at dawn -only time weather was bearable- for a trip out in the jeep. Then flaking motionless in the pool all day followed by second trip at twilight. And this wasn't even in their summer!

any holiday will be successful with a close-knit family

I would think Italy, as there is a lot of appeal across the ages. My kids love the food and there is so much history and culture that older family members can enjoy.