Help with Itinerary
 

My husband and I are active adults who will be visiting Italy in September. We'll be flying into Venice (3 days) then taking the train to Florence (5 days) where we plan in taking a day tour to Sienna and one toTuscany. After Florence we'll take the train to Cinque Terre (2days) with a stop over in Pisa. Then on to Rome (4 days) before heading south to Sorrento (3 days) and back to Rome (1 day) before flying home because we couldn't get flights out of Naples. We really want to visit all these places and explore the countryside but are wondering if it's worth dragging our luggage on all those trains. Would we be better off taking day trips to from Florence to Cinque Terre and Pisa then take the train from Florence directly to Rome?

That is too many hotel changes for my taste (remember, you generally lose 1/2 day when you change cities and hotels). So yes, I would do Pisa (and Lucca) as a day trip from Florence. Frankly I would skip CT and add that day to Rome or Sorrento, but that is just my opinion.

Also, go directly from Florence to Sorrento and keep all your Rome time together at the end.

Ekc's advice is spot on. Skip CT this time. Add that time to Sorrento (and AC) and put all Rome time at the end. That will be perfect sight-wise and logistically.

I agree--put Rome at the end.

It's Siena, not sienna. And you can go on your own. Be sure to visit its duomo - the equal of any in Italy.

I agree that Cinque Terre is out of the way, but perhaps it might fit better if taken in this order with your proposed number of days in each place. I would steal a day from Florence and add it to Cinque Terre to put more space between your travel days, or just do Pisa if you feel like it as a day trip from Florence.

Day 1: arrive Venice
Day 2: Venice
Day 3: Venice
Day 4: train to Cinque Terre
Day 5: Cinque Terre
Day 6: train to Pisa, then to Florence
Day 7: Florence
Day 8: Florence (day trip to Sienna and Tuscany)
Day 9: Florence
Day 10: Florence
Day 11: train to Sorrento
Day 12: Sorrento
Day 13: Sorrento
Day 14: train to Rome
Day 15: Rome
Day 16: Rome
Day 17: Rome
Day 18: Rome

I agree that I would probably choose to visit Cinque Terre OR Sorrento, but not both.

(Siena and Florence are in Tuscany, so I assume your reference is to the countryside.)

We really want to see Cinque Terre but agree moving it after Venice and moving Rome to the end of our vacation makes more sense.

Florence is the capital of Tuscany and Siena is only one of the many towns there you can visit. What other one do you want to see - and will you try to do by train (difficult) or get a day bus tour or rent a car?

IMHO you are spending a lot of time moving around - so unless you really want to hike between the 5 towns villages I would bag it for Sorrento/Amalfi coast.