Italy with baby and teenager

[AnythingNotEverything]

I really hope I'm not searching for the holy grail ...

In May half term next year, I'd like to take DP, DS (14) and baby (7 months) to Italy for a week. I am hoping baby won't be crawling, but will be starting to eat real food. DS is easygoing, loves pizza and pasta, and is happy on holiday as long as he connects to wifi every now and then.

I was hoping to do 2-4 days each in two city bases, the cities we've brainstormed to visit include Venice, Rome, Pisa, and Pompei.

I hope we'll be able to book an apartment rather than teeny hotel rooms. No idea how much we're prepared to spend - depends on how amazing it might be!

Am I crazy?! Am I going to regret this?!

Any advice, experience, or book recommendations will be gratefully received!

TIA!

I can't see why it won't work, particularly as you want to go before your baby is mobile and you will have a good routine established by then. I'd go for 3 to 4 nights in both places as it may be quite tiring packing up after just 2 days. I stayed in a place called poggibonsi which was an excellent area for visiting Sienna, Pisa and Florence. In Rome it's worth pre booking tickets to Vatican and Colloseum to avoid long queues.

Forgot to add visiting all those places may be slightly too ambitious in week as they are quite spread apart. Another suggestion is an Italian cruise, Costa does them. Lots for your teeanage including wifi.

That's the idea - settled and stationary baby, hopefully some sort of routine (maybe even sleep!), but not too hot!

Thanks for you advice - I wasn't even sure where to start, so you've helped!

Pompeii would work better if you have a baby sling as bumpy ground but worth going for your DS. Mine really wanted to go and see the bodies there as they had learnt about it at school!

If at all possible, you should consider allowing the teenager to bring a friend. I wish we had when we took our dd1 aged 14 on holiday with our younger two (aged 6 and 8) in July. She missed her friends, and whereas her sisters made lots of friends, she didn't. It's harder for teenagers!

Have you thought about using Naples as a base to explore Pompeii? I love Naples, there's an amazing museum of archaeology there, and the best pizza ever.
I think I would do 4 days in Rome, then get the train to Naples for the next 3 days.

Alfalfa - your itinerary looks great!

We have taken a friend away before, but were hoping we could do this without. As he's been an only child such a long time, we do a lot as a threesome, so he's always included. I'm not one to fuss over a baby so hope while not yet moving this wont change too much. Maybe baby will think otherwise!

Thank so far!

Florence is lovely but it will be very hot and busy.
Your teen may not enjoy it so much there as Rome or Pompeii.
It's great if you're into art and of course it's a beautiful city but I think Rome is very visual. So much to see everywhere.

I would go to Rome , Naples and Pompeii.