I Need To Cut Time Off

Wow. Where to begin?
1. I strongly recommend a guidebook like the Rick Steves Italy book to help you figure out where to go and how much time to spend.
2. What research have you done so far? (For example, why on earth do you want to go to Genoa?)
3. And why five days in the CT?
4. What time of year will you be traveling?
5. How many are in your "group"?
6. Are you the one coming up with this itinerary for everyone?

Skip Genoa, trim the CT down to 3 days & forget Sicily. That done, you will still have too much crammed into too few days. When is the trip set for?

Michael's questions will be helpful to giving you further advice. For now though - Lucca and Siena are both cities you could see as a day trip from Florence. (Assisi would even be possible as a day trip, just a longer ride). Doing day trips allows you to spend more nights in one place and then you don't have to move your stuff around as much. Also make sure you streamline your travel in a logical path (somewhat North to South, likely). Also - when you say you plan to spend two days in Sicily - where are you thinking? Palermo? Another city? If you are planning to go by train, it takes a long time to get there. If you are planning to go by budget airline, there are many restrictions on luggage and such. That all must be factored in to your itinerary planning. I haven't been to CT, but it seems that most tend to think 5 days is too long - that's another place where you can cut time.

.

Remember that when you have two days, you only have one night in a city and you don't have a full day to explore. It's nice to spend at least two nights in each destination. Here's just a possible example of how you could arrange a trip with some of your destinations listed:

Day 1 leave USA (I'm assuming that's where you're coming from), Day 2 arrive Venice (3 nights). Day 5 head to Florence for 5 nights (see Lucca and Siena while there, 2 full days for Florence). Day 10 head to CT for 3 nights. Day 13 head to Assisi for 2 nights. Day 15 Rome for 4 or 5 nights. From there you could head to Amalfi for 3 nights or so. If you do want to see Sicily, you would probably want to fly from Naples because it's a very long train/car ride otherwise. Otherwise, if you cut Sicily you could spend more time up north near the lakes, more time in Tuscany/Umbria, etc.

First off, you say 25 days total and then list 30 days for the cities you want to visit and don't appear to account for travel days. So, that being said, you definitely need to make some adjustments. Disclaimer: any suggestions I make are based totally on personal opinion.

I would say:

Genoa, Sienna, and Lucca - 1 full day each. You can do Sienna and Lucca as day trips from Florence.

Assisi, Venice - 2 full days each (3 nights).

Rome and Florence (for day trips) - 3 or 4 full days each (4 or 5 nights).

Cinque Terre and/or Amalfi Coast - 3-4 days each depending on how much hiking you want to do.

You may not have the time for Sicily based on travel time getting there and back and it deserves at least 5-7 full days to get a good taste of it.

What Nancy said. Sicily for two days isn't worth the trouble.

The rest is arguable for personal preference, but the CT is an overkill - - about like taking out fire ants with napalm.

Hi Phil, in 2013 i spent almost a month in Northern Italy (Rome and north). While I had a wonderful trip, i came away with two important lessons for the future: (1) Don't move from one town and hotel to another too often, especially when traveling by public transport, as each move really eats up a lot of time and energy; and (2) don't just grab any ole thing to eat only because it's time to eat, especially to eat it on the run, when there is so much great Italian food to sit and really enjoy. I think it's usually even better to go hungry a little bit, in order to enjoy a good sit-down meal a little later.
i share that, mostly just to agree with others that your initial expectations seem way, way over-stretched, and also do not allot various locations the amount of time they really deserve, some too much, some too little. Of course where you choose to ultimately visit will depend a lot on the particular interests of yourself and others in your travel group. Are your prime interests fine art and architecture, or outdoor activities, or experiencing Italian culture and history, or fine food and wine, or what?
I myself am headed back to Italy this May to focus on the south, mostly two weeks in Sicily and a week in the Naples and Amalfi Coast area.
All that said, I would suggest:
1. Leave Sicily for a future trip. It is distant, quite large, very interesting and diverse, and deserves real exploration, not just a momentary stop.
2. Cinque Terre is very nice for a couple full days, if the season is right and the weather is good. I think 5 days is too much given your other plans.
3. Venice, Florence and Rome are all wonderful, and quite different. i would suggest spending at least three full days in each.
4. i have never seen anyone else list visiting Genoa as a priority before. I've never been and would skip it unless it was on my route anyway, then I might stop to take a look.
5. The Amalfi Coast is some distance south of Rome, and travel and settling into lodging would take you at least a half day each way. Including it will require compromising in other areas.
6. Siena, Assisi and Lucca are all very nice. There are pros and cons to spending nights in these towns, as opposed to day trips. Depending on the season, day trips can put you there just when all the other daytrippers are also there, so a heavily touristic visit. Often the most magical times in these towns are the evenings and early mornings, which you miss on day trips. Of the three, I think Lucca is the most skippable.
7. You also asked for suggested additions. If you really thin out your current list of visits, you might consider Orvieto (in Umbria near Rome), San Gimignano or Volterra (both in Tuscany) all of which I really enjoyed last year, or Verona or Ravenna (a little out of the way), which i will be visiting this May. Also for scenery and outdoor activities, the Dolomites and the various northern Italian lakes offer a lot to see and experience, depending on the season.

Hope that helps. With 25 days to explore Italy, you really can't go wrong. Enjoy!

In chorus with so many of the others, I say omit Genoa altogether. Not that much of interest there, especially for a first-timer. If you must do the Cinque Terre (and I think they are boring little villages that also shouldn't be on a first-timer's list), cut the time to 2 nights. You'll see plenty of beautiful coastline on the AC. Sicily is wonderful; but if you can't give it at least a week, save it for another trip. An overnight in Assisi is adequate for seeing the important places. Do Lucca and Siena as daytrips from Florence, making the time in Florence 5 days. I would add a night or 2 to the Amalfi Coast. Sorrento is a good base for visiting Pompeii, Amalfi, Ravello, Capri, and even Paestum. Rome needs more than 3 days, 4 or 5 at minimum. So, if you give Rome, Florence, and the AC 5 nights each, Venice 3, CT 2, and Assisi 1, you'll still have 4 days to play around with, assuming that you didn't count your arrival and departure days in the 25 (if you did, stop reading now). Given what you said about your interests, you should consider going back to the Florence just 3 days plan + 1 day for Siena and using the 5 remaining days for an exploration of the Tuscan countryside, which could include Lucca and several other very attractive towns. Hope I got the numbers right. After you get your itinerary settled, you should come back with the specific questions you'll have about the various places. Lots of us have lots of experience with Italy and enjoy helping.

25 Nights:
Fly into Venice
Sleep Venice (4 nights) {1 more than normal to account for jetlag recovery}
Train to Verona [half day]; Train to Florence
Sleep Florence (3 nights) {1+ less than normal because you said yall are not that into museums}
Bus/Train to Lucca [half day]; Train to Cinque Terre
Sleep Cinque Terre (3 nights) {I will keep it at 3 instead of 2 since it seemed to be your highest priority}
Train to Pisa [half day]; Train to Siena
Sleep Siena (2 nights)
- Rent car in Sienna for rest of Tuscany/Umbria (get special guidebook for scenic driving routes, tips, and itinerary suggestions)
- Day 1: See San Gimignano/Volterra/other Tuscany (sleep Volterra or any town)
- Day 2: See Tuscany/Umbria (sleep any town)
- Day 3: See Umbria including Assisi (sleep Assisi or any town)
- Day 4: See Umbria to Orvieto; Return car in Orvieto (sleep Orvieto)
Train to Naples
Sleep Naples (2 nights)
Train to Pompeii [half day]; Train to Sorrento
Sleep Sorrento (3 nights)
Train to Rome
Sleep Rome (4 nights)
Fly out of Rome

If I added 1-2 more nights I would just add them to Rome at the end.

This is very subjective because different people have different preferences. But I'll give you my take.
Venice: at least 3 nights (2 full days) are good. One full day for Venice then one for the islands of Murano and Burano.
Genoa: unless one has a specific reason to visit Genoa (e.g. family to visit) I wouldn't include it in an itinerary for a first time visitor.
Florence: the city itself probably needs at least 2 days on its own (3 nights), however many people use Florence as a base to visit the many Tuscan places nearby, therefore they add as many nights as day trips they want to take to the other places. Within one hour or so from Florence you can find the following: Pisa, Lucca, Siena, San Gimignano, Volterra, Chianti hills and many other places.
Siena: You could actually eliminate any nights here and visit from Florence. If you decide to spend 3 nights, use one full day to visit Siena and one full day to visit Montepulciano and Pienza, near Siena.
Lucca: Same comments like for Siena. You can visit from Florence. If you want to spend a couple of nights there, use Lucca as a base to visit nearby Pisa for a few hours.
Rome: 3 or 4 nights is a good starter for a first timer. 3 full days give you an adequate amount to have a taste of the Eternal City. If you add more, use a day to visit Orvieto on a day trip.
Assisi: 2 nights (1 full day) is more than enough to visit Assisi. If you add more, use it to visit nearby towns (Spello, Gubbio, Perugia), although a car might be useful.
Amalfi Coast (or nearby Sorrento): 4 nights (3 days) is good. One day for the Amalfi coast (Positano, Amalfi), one day for a day excursion to the island of Capri, one day for the Archaeological wonders of Naples and Pompeii.
5 Terre: 3 nights (2 full days) is more than enough. Actually I couldn't see myself there more than 2 nights (1 full day).
Sicily: It's a huge island the size of Massachusetts and Rhode Island combined, it's also far and hard to reach from all other places you mentioned (best way is by airplane). It has the richest history and the most to see of any regions in Italy. If you don't have at least a week to devote to it, you may want to leave it for your next trip to Italy.

What Roberto said. I do prefer a two-night stay rather than a daytrip because you have the smaller cities to yourself after the daytrippers leave, but compromises must be made.