Two Weeks in September

You must realize that 2 nights in a place is only one full day at that location (plus a few hours of the day you arrive, which you will use to get oriented with the new location). Also changing hotels takes time, as that process entails packing, checking out and checking in paperwork, unpacking again. Sometimes, if two destinations are sufficiently close, it's faster to take a day trip from the one place than to move to a new hotel in the second destination. In your case since Florence is the capital and largest city in the region of Tuscany, to visit Florence and Tuscany, you should stay in one place only which you can use as a base to visit both the city and the region around it. If you rely on public transportation, I suggest to use Florence as a base, since the city is also the transportation hub of Tuscany.
In my opinion your stay in Sorrento is too short. Getting there is a bit convoluted and there are too many things to see. To me 3 nights in Sorrento and 1 in Naples (before the flight out) is the minimum. If you don't have the time, consider ditching the Naples/Sorrento area and adding that time to the other locations according to your preferences. Or alternatively remove the Cinque Terre and use the saved nights for the Naples/Sorrento area (also the other locations could use at least one more night each as well)

This is an alternative idea to hit all your places. Since departing from Naples requires spending the night in Naples (the flight is likely super early and Sorrento is too far from the airport) you should consider flying home from Rome, which you would leave as your last destination. This is an alternative allocation of your 15 nights (in this order):
Venice 2
Florence (incl. trip(s) in Tuscany) 4
Cinque Terre 2
Sorrento 4
Rome 3
I've decreased one night at the Cinque Terre and given to Sorrento as there is more to do there, but it's up to you.
Be aware that the trip from the Cinque Terre to Sorrento will take about 6+ hours (train(s) to Naples then commuter train to Sorrento).

Thank you for the suggestions. That may be something to consider. Either that or we may add more days to each place and simply end in Rome.

I would not spend fewer than 3 nights in Venice and 5 in Rome and Florence especially if you plan a day trip into Siena or other Tuscan town. This trip as writ is all about checking in and out of hotels, rushing to and from trains, and getting from one place to another. Way to much getting there to being there. One night in Naples gives you nothing. One full day in Florence is IMHO not worth doing unless you want to be able to say you were in Florence and maybe look at the view -- this is a town that requires time to actually appreciate what it has to offer i.e. its Renaissance art heritage. Three nights in Rome is one day for the Vatican and one day for historic Rome -- more than rushed. Sorrento IMHO is not worth a visit for a day. It is a good jumping off place for Pompeii but if you want to experience this part of Italy then you need more time.
Less is more -- i.e. less travel gives you more time to see and do what you come to see and do.

Venice 2, Florence 4, Rome 5, Sorrento 3, Naples 1.

My 2 cents:

1. Use Florence as base for Tuscany. Maybe consider travel to Rome via Pisa just to take photo.

2. Bypass CT to eliminate travel and to free up nights elsewhere. CT is different from Amalfi, but you will get a similar and imo more improved experience with the additional time and reduced travel.

3. More time in Rome because so much to see.

4. Fly out of Naples. If you fly out of Rome, consider that you are doubling back which means you lose half a day in travel.

5. You may consider just taking a cab directly from Sorrento to Naples Airport, about 90 minutes. If you do that you can free up another night to put somewhere else. Naples would be a toss up if it were me. When we visited the area, our driver described Naples as "hell" and it did look run down as we whizzed by on the highway. My sister stayed there 3 nights a month later and said it was the most interesting place in Italy. Maybe it was because she was eating authentic pizza in Napoli while there was gunshots outside the restaurant. LOL. If you opt out of staying in Naples, consider add to Venice to give you 2 full days to see more and to get over jet lag. Or add to Rome.

Last October, I did a 2 week (3rd through 18th) trip to Italy. We flew into Venice and out of Rome. We spent 5 nights in Venice, 5 nights in Florence and 4 nights in Rome. (Three days was not nearly long enough in Rome but we knew we’d be back so this was to learn the lay of the land.) Although many escorted tours (like Rick’s) move you along rather quickly, doing a self-guided tour is altogether different. Minimizing the number of cities and stretching the stays out provides you a lot more flexibility and allows you to get to know the real flavor of the city. These longer stays also allowed us to day-trip to the cities of Vicenza and Padua as well as places like the Dolomites and Chianti.

The slower pace in each city also allowed us to stay in apartments which are much more comfortable (and often cheaper) than hotels. In addition to being roomier and providing more than just a bed to sit on, they have kitchen facilities (great for breakfasts) and usually have a clothes washing machine.

Bottom line, I think you‘re trying to cram way too many places into your itinerary. I have a total of 8 days each in Venice and Florence and I feel I’ve only scratched the surface of each city. I’m already planning my next vacation; probably a week in Rome and a week in either the Cinque Terra or Amalfi Coast.

I would go with Roberto's suggestion above.

Venice 2
Florence (incl. trip(s) in Tuscany) 4
Cinque Terre 2
Sorrento 4
Rome 3

I like the four nights in Sorrento, as it gives you 3 full days for excursions to Pompeii, Capri, Positano, Naples, etc.

"want to be able to spend the appropriate amount of time in each place and not feel too rushed"

According to you, you will have 15 actual nights, so try to plan around that.

You will arrive in Venice around noon, but it may be a few hours before you actually get to your hotel. And you may be jet-lagged. So you get a few hours to sight-see and eat dinner. Then you only have the next day to actually see Venice, since you leave on day 3. Venice, IMO, needs a few days (and nights).

My idea--
Venice, 3 nights
Florence, 4 nights, with day trips to Siena, Pisa, and/or Lucca
Rome, 3 nights
Sorrento, 3 nights
Naples, 1 night

Or, go to CT for 3 nights, and skip Sorrento and Naples, and fly out of Rome.

This still gives you 1 extra night to add where you wish, depending on your interests. Most people either go to CT or Amalfi, but not both if the time is limited. Save one for your next visit!

a day trip to CT would be enough for me. Overrated tourist trap. Been there. Beautiful coastal towns. But that's it. overpriced menus, bored waiters, crowded walkways. No Thanks. But hey, find out for yourself.

The problem with doing CT as a day trip, you go there just when all the tourists are there, too. By staying there, you get the less crowded mornings, and fun-filled nights, when tourists are gone. That is the CT I love!

The best order of my proposed itinerary is
Venice - Florence - Cinque Terre - Sorrento - Rome

Going from Venice to Cinque Terre is a long trip with at least two changes.

Cinque Terre to Naples requires train changes only in La Spezia and Rome. No need to change in Pisa and Florence, as the train from La Spezia to Rome takes the coastal route. And if one departs from Monterosso, there could be only one change (in Rome).

Departing from Naples may seem a great idea, but unless you plan to stay in Naples, catching a 6am flight out of Capodichino from a hotel in Sorrento is not going to be fun.

I also agree with the Roberto's suggestions in terms of the order of cities. It's more efficient in terms of transportation times to travel Venice > Florence > Cinque Terre > Sorrento > Rome. It would even be more efficient if your return flight departed Naples so you could make Sorrento your last stop. I would also suggest the number of nights in each place that Roberto mentioned in his 10:20 post.

Which of the five towns in the Cinque Terre are you planning to stay in? In any case, I'd suggest getting a room booked SOON, as it can be busy at that time of year.

As this is your first trip to Italy, there are some potentially expensive "caveats" to be aware of when using trains or other public transit. If you need more information, post another note.

I appreciate all of the input. Planning a trip to a country like Italy is such a daunting task. At first I thought that 2 weeks was too long, now I know it's not nearly enough! I'm now leaning towards a more northerly trip, Venice/Florence/CT and ending in Rome. That way I can add extra days to a couple of those places, get the full experience. I see no problems with a return visit down the road to hit the south and possibly Sicily. That being said, is a day trip from Rome to Pompeii feasible?

A day trip to Pompeii is feasible but will eat up most of the day of course. Our first visit to Rome in 08 we did 5 nights and did a day trip to see Herculaneum and even had time to go up top Mt Vesuvius...and this was after bungling up the train stop to get off for Herc (and having to wait an hour for a train to take us back to the right stop - it was a Sun). We spent about 2.5-3 hours at Herc, stopped for a pizza and the trip up Mt V. Even after all that, we were back in Rome by 8-9pm or so (leaving about 9am taking the fast train).

Depending on what you want to see at Pompeii, plan on at least 4-5 hours. We did one of the tours you join at the train station in 2014 - it was 3 hours and we really only saw the highlights (and we stayed in Naples the night before and stopped in Pom on our way to the Amalfi Coast) - I'm sure we could have spent another two hours. That being said, if you are still doing Rome for 3 nights only, I wouldn't do Pompeii. We've have two 5 night visits to Rome and I could still go back for a week to see everything I missed...

Thanks for the heads up Roberto re trains from Cinque Terre. I always thought the fastest route was through Florence and not along the coast. This is good information to know. Thanks again.