Capri or Siena?

I think I would do Capri as a daytrip from Positano. I enjoyed the boat ride around Capri and a full day exploring the island. I would then add those 3 days (one each) to Venice, Florence and Rome. Or stay in a small village. I've only stayed in Assisi so I can't recommend any other villages. We absolutely loved Assisi! That would give you something new to experience. I don't think you can go wrong. I'm sure you'll get a lot of good advice on this forum. Your trip sounds wonderful! I would love to go back!

Having visited all the places u list , I suggest u include Siena easily done by bus from Florence. Stay 2 nites in Siena, 1 day for Siena sights and 1 day for Pienza and Montepulciano by bus from Siena, so easy. Reduce Capri to 2 night, and reduce Positano to 3 nights. I am not saying Capri and Positano are worth less but to accomodate a easy trip to Siena, well worth it.
E back if u have more ques. I truely love the area u are going to and could spend weeks there. Just figure your next trip to Italy could include more of S. Italy and maybe Sicily. I am headed to Sicily next wk.

Capri is beautiful, indeed, breathtaking. Is it worth 3 days? I was ready to leave after a few hours. It is a great day trip from Positano and while it is romantic, Positano seems even more so. I would add another night to Venice, Florence and Rome, each, and do the daytrip thing to Siena, as well.

I think I'd add time to Florence AND Venice and cut Capri.

You only have 2 nights in Venice and one is arrival day, when you might be wiped from a long flight, so you might want to do 3 nights, 2 full days there. Then again, if you've been and think other locations would be more your thing, then maybe that's enough.

But Florence also deserves more than 1.5 days. As you'd already be spending some time in Positano, I don't know as you need to have 3 days on Capri. We enjoyed it and I'd recommend staying on the island versus do it as a day trip but not at the expense of Florence/Venice. Either Siena or Lucca are easy trips from Florence, and either (I think?) would be new to you.

But what about your husband? Does he have some idea of the places he'd be most interested in?

I propose:

Venice 3 nights (visit to Murano/Burano/Torcello or Padua during your stay)
Florence 4 nights (day trip to Siena on one day, possibly even somewhere else on another day, like Lucca or Arezzo or Pistoia, etc.. Although Florence will easily take at least 2 days of your time)
Positano 4 nights (while here take boat excursion to Capri for a full day, plenty of companies to choose from. Visit Pompeii while here, or on the way from/to there)
Rome 3 nights

Total still 14 nights.

No need to stay in Capri for 3 nights. Expensive, pretentious ultra rich Italians/Europeans, and not a whole lot to do to keep you busy for 3 days without a yacht. A day trip is sufficient, IMO.

If you like the sea stay longer in Positano & Capri, mountains, Tuscany!

3 Venice
2 Florence
2 Sienna/area if you like hills & mountains if not 3 Florence 1 day trip
2 Positano
2 Capri
3 Rome

How anyone who can dish Capri as only worth a few hours is beyond me! I stay every year for a week and there is always something new to discover, if you walk and look...not just tick off the top 5 tourist sights on a day trip! Capri is magical at night!

Remember water shoes for Capri & Positano!

Enjoy!

Thank you all for the great advice! I think I will be definitely adding some more time in Florence and will do a day trip to the Tuscan countryside.

Both are wonderful in their own way. Capri is absolute magic. Can't understand why some so easily dismiss it, I preferred it greatly over Positano myself. I would at least day trip there from Positano. Easy by ferry.

I only spent about half a day in Sienna but it was lovely, small enough to cover quickly.

Well the comments above are wonderful for sure. If this is your first trip to Venice I would be hard pressed to recommend you ONLY spend 1 day there. If you have been there and know what your will miss by not spending more time, ok.

Capri is a very beautiful place but a day trip kind of visit is enough for me. It is overrun with tourists and caters to high end shopping. The island, geographically speaking, is stunning! Siena requires a visit, so do both.

I have gone to Italy many times over the years and have been everywhere you listed. I would definitely recommend staying in Florence for two extra nights so you can use up at least one of those days visiting some hill towns and still see Siena. Take two nights off Positano. Since you have never been to Capri I would keep those 3 nights. Yes some of Capri is pretentious but it's worth staying at least 3 nights given how much there really is to see and do there. There is an extraordinary hike to Villa Jovis that is well worth it. Not to mention getting to the Blue Grotto and the gardens of Augustus. Also when you get to Ana Capri there is Villa San Michele and the chair lift to Monte Solaro where you can spend some quality leisure time sipping an aperitvo and enjoying the stunning views. There are a lot of Mom and Pop stores there as well where you can find high quality ceramics, clothing and sandals. We stayed at Hotel La Minerva and once there you won't want to leave. The owners take amazing care of their guests and will arrange anything you need. The nights in Capri are a completely different experience than the days filled with tourists that flood the main streets. Capri never gets old for me because once you know how much there really is to see and do, those three nights will fly by.