Two centre holiday or interrail? Who to book through?

[overwhelmedbyitall]

Hi,
We're planning first overseas holiday in years and no idea where to start, who to book through etc.
We are 2 adults, 2 kids (12 and 14 year olds) Want some beach/lake/water but other stuff to do too - history, walking etc.

Done AirBnB and camping in France before and and an all-inclusive hotel in Canaries ( which was nice enough but not really us!).
This time we're thinking of a two centre trip, or even interrailing/road trip. We'd like an apartment or villa more than 4 of us in a hotel room for a week with a couple of nights in other places before and after.

So overwhelmed with websites but would appreciate any pointers/recommendations!

Honestly I would just pock a couple of the places in Italy and book accommodation and flights.
Train between destinations.
The trains in Italy are easy, reliable and cheap

We are thinking of a two or three destination this summer. Flying into Lisbon, spend a few nights there, maybe go to Cascais for some beach relaxation, then train down to Porto which is a great place to visit.
I use booking.com mostly for booking as they have a mixture or hotels and apartments, or sometimes VRBO or Airbnb has a better selection.
I'd recommend booking cancellable options where possible to give you flexibility in case plans change.

We interrailed through Italy - Sorrento (went to Pompeii), Venice, Turin and then Paris on the way back. Would have stopped at Rome as well but we’d been there recently. We mostly used Airbnb. The trains were great but you needed to book mostly and there was a £10 ish charge per seat. Really enjoyed it though.

This. You could do Venice and Jesolo beach or Lake Garda, Rome and Ostia beach, Naples and Sorrento/Amalfi, Catania and Syracuse or Mazzaro with Taormina... the possibilities are endless. Just book flights with Easyjet or Ryanair and get Airbnbs.

We did this in Spain, train from Madrid to Malaga. But if planning in Spain, their super fast trains - which are great btw - can’t be used with an inter rail pass, they needed some kind of complicated reservation so we didn’t get the Spain rail pass, just ended up buying the individual tickets on trainline

Ah yes we did a great two centre trip by flying into Naples, got a transfer to Sorrento ( Rota Suites so you don't all sleep in one hotel room), train back to Naples then high speed to Rome.

Sorrento is a great base for visiting all sorts of places - Capri, Pompeii, Herculaneum but also relaxing a bit. Means you only need two sets of accommodation and the trains are relatively easy to book ( you only need to reserve Naples to Rome).