We have so far never taken our 2 kids abroad (3.5 years and 10 months) but are thinking of going in October for a week for my birthday. Wed like to go somewhere warmish but don't want scorching heat so are thinking portugal.
My main question is what do you do with the kids abroad? How do you entertain them? Our youngest will be nearly 14 months by then so could be walking and eldest will be just over 3.5 years. Will a holiday abroad be incredibly hard work with little enjoyment for us? We're thinking of a villa holiday but open to ideas.
My kids were more than happy spending mornings on the beach, having a nap and afternoons in/by the pool, at that age. In fact they're still happy to do that in their late teens!
An small apartment complex might be better than a villa, so you have a baby/paddling pool, small play area and other kids to play with. If you buy a small inflatable boat, either there or take one (poundland sometimes sell them), they can have 'boat trips' in the sea/pool and your youngest could also use it as a paddling pool or baby bath!