2 weeks Italy itinerary - feedback

If you are staying in Siena for three nights, why would you use one of your Lucca days to explore Siena? Pisa would be about a half-day from Lucca.

Lucca is a lovely town to overnight (or two) in, I would keep your itinerary as it is (except for that Siena exploration thing from Lucca).

A daytrip to Capri from Roma is ill-advised, to say the least. Travel will eat up at least a half-day, and ferries are weather-dependent (should be fine in September, but...).

If you are considering Florence/Siena/Pisa/Lucca then it would make sense to simply base out of Florence. There you have a more flexible and frequent train schedule and you will spend less time getting settled. Pisa is really just a half day and you could wrap that into your journey to Milan.

Enjoy your journeys!

I'm with Zoe. I think it's worth spending a few nights each in Siena, Florence, and Lucca. Especially Siena, which I think is particularly delightful at night.

Is there a reason for going from Siena to Lucca to Florence? You don't say whether you're traveling by car or by public transport, but check out routes and schedules and you might find it makes more sense to reverse your visits to Lucca and Florence. I guess if you're going by train, you have to do some backtracking either way.

Enjoy!

Sorry, that was a mistake saying explore Siena while in Lucca. I meant to say explore Siena while in Siena. Travel to Pisa from Lucca.

We are taking Public transport for our travels between cities/towns. I get wanting to have a 'home base' and travel to the other towns to explore, but, I do at the same time like the idea of being able to stay into the evening to see the towns at night and then in the morning. So, it sounds like taking a couple nights in Lucca will be worth it......
The trip down to Capri is a thought, when we were there last time, we didn't get to see it due to weather. I get it is a bit of a haul.....
Suggestions for a day trip out of Rome?

Day trips from Rome - Tivoli/villa d'Este/Hadrian's Villa, Ostia Antica (it's a 1/2 day, but you could spend the afternoon along the beach), Orvieto

I'll agree with skipping the day trip to Capri; it's really much too far from Rome. If you've only 'done the Vatican and Coloseum thing', there's a great deal more to discover in the city itself without taking any day trips at all, especially with only 2.5 sightseeing days to use there, and a potential case of jet lag to deal with on that 1/2 day.

If you'd give us some idea of the sorts of things you enjoy, we could makes some suggestions?

I, too, like to wake up and go to sleep in a city, to get a better feel for it. I don't object to one-night stays as long as there are not two in a row; your plan looks good.