2 week itinerary Florence, Rome, Pompei, Amalfi and ancestral home in Tropea?

Tropea is the outlier, and it will really eat into their time. While I don't think this matters much, most would not recommend Calabria for a first visit, but for geography and money/time-saving alone, I would be inclined to skip it unless they think they will never set foot in Italy again (a depressing thought). It is the only part of this itinerary that will require any real effort, so I would triple confirm they want it that bad before putting considerable effort into figuring out the logistics.

ETA They should also be aware of the Jubilee year and how it will affect things, primarily Rome: https://www.travelandleisure.com/rome-jubilee-2025-what-travelers-should-know-8721233

A lot has to do with their interests. What do they want to see? What do they want to do? Hone down the stops based on their interests. I agree that Tropea is inconvenient because of how far it is from other potential visits. If they have 14 days, remember that the arrival and departure days don't count. Also every time you change locations, it will take half a day or more. Your brother and his wife should look at travel guides to see what is available in various cities and choose what they really want to do. If visiting Tropea is a must, consider not basing anything north of Rome (except a possible day trip to Orvieto). Italy is a country to be savored, not rushed!

Hello mbnuovo, and welcome to the forum,

Assuming visiting Tropea is the reason for the trip and everything else is built around that I would suggest flying into Rome or Naples and travelling to Salerno. Salerno will give them access to the Amalfi coast and Pompeii and be a staging point for Tropea because it is really far south. The best case train from Salerno is probably about 4 hours to Tropea and I will assume they need at least 2 nights there - one full day - at a minimum to visit the old ancestral home. I would suggest more since there is at least 8 hours of train travel either side of this stay,

So something like fly into Rome:
1 night in Rome (travel to Salerno 3 hours train)
4 nights Salerno (3 days - 1 Pompeii and 1 day trip to Amalfi) Travel to Tropea (4+ hours train)
3 nights Tropea (2 days on the ground) Travel Tropea to Florence (8+ hours of travel)
3 nights Florence (travel to Florence)
3 nights Rome - fly home

With 14 nights I think a sensible schedule would look something like this. This assumes they are happy with a day trip to Amalfi and not staying there. If they want to stay then you would probably need to drop Florence. This schedule does not allow for a ton of days trips - you could do one day Florence and one day Siena - but this schedule already short changes Florence at 2 days so I would suggest not.

You can try and steal a day here or there (Salerno, Tropea) but if they are not experience travellers I think you need to allow them some time to breathe and get acclimated. And if someone isn't guiding them then they will need to make all these connections on their own. Honestly I think they either need more days or settle for "sampler platter" fast visit to Florence and Rome.

If Tropea is the reason for the trip I would suggest easing the schedule and dropping Florence or doing it as a day trip from Rome if they can't add more days. Planning is often the case of making hard choices from a long list of wants.

Hope that helps,
=Tod

And for sure they need to add as much additional time as possible-if they are employed, they need to make sure the trip starts and ends on a weekend.