itinerary

You’re not planning to see Venice? 5 days in Siena? Siena is great but you could give it 2 nights and at least 3 nights to Venice. I returned yesterday from 9 days in Venice and feel I must return, there’s so much to do and see. There are no cars so it almost has a countryside or small town vibe.

Since you are not sure about Cinque Terre, those 2 days could be allocated to Rome, 1 day extra, and Venice, 1 day extra. Also, I would leave Milan for another trip.
Fly into Rome
Rome - 4-5 days
Assisi- 1-2 days
Florence- 4-5 days, day trip to Siena and Lucca
Venice- 4-5 days, use Venice as a base to train into Padua and Verona
Fly home from Venice

This itinerary will give your friends a good taste of the variety of Italy. You might even consider reversing the order by flying into Venice as it’s a good place to unwind, relax and ease into Italy. See Rome last as it is so intense and you can fly home from there.

I’m sure you will have lots of excellent suggestions from others.

I like Judy's recommended itinerary better than yours.
Five days in Siena doesn't make much sense, you can see that city well in one or two days. Use Florence as a base for Siena.
Assisi is great, but you can do it in a day, so you can see nearby Perugia as well.
Venice is incomparable and beats the heck out of CT. Milan is great, but out of the way.

After you figure out where you want to go we can be more helpful about mode(s) of transportation. A rental car would be very helpful for one or a few days while you're in Tuscany; it's much easier to see multiple small towns in a day if you don't have to worry about bus schedules. Assisi has enough to see that I wouldn't try to combine it with another destination on the same day, but the little hill towns in Tuscany are a different story. For connecting major cities trains will be much faster

You do need to be careful driving in Italy. There are speed cameras on the highways, and the historic districts of many towns and cities are no-entry zones for non-residents. You can rack up a lot of traffic tickets if you don't do some pre-trip research about the rules. No one will stop you during your trip. The cameras will just keep taking pictures of your license plate and the tickets will find you at home months later.

I respectfully disagree with those who say 5 days is too much for Siena. True, Siena itself has enough of interest for a couple days and not much more, but it is a good base for exploring Tuscany. You could easily spend an entire long day heading south toward Montalcino, Pienza, Montepulciano, the abby of Sant'Antimo, and the many other delightful towns in that area. You could spend another full day going north toward Volterra and San Gimignano. And Siena is a delightful place to come back to for dinner and a passeggiata.

When I was in Siena, I rented a car for two days to do the day trips I described. Otherwise, I took buses and trains between destinations, and that worked fine.

Nothing wrong with carving out some time for Venice, though. It's such a fabulous city.

It seems to me that you are planning a vacation that you and your friends have yet to finalize. That's good - planning and re-planning can be, and should be, part of the fun. I would suggest getting out your RS guidebooks and over pizza and wine (Italian, of course), the 4 of you come up with a list for each city and prioritize it. How much time do you need? Did you plan for the 'riposo' hours in the afternoon when many places close up. (Sorry Rick, but it always takes me longer to visit a site than you do.) Getting tickets for museums that have secured entry times will help you save some time since lines can be long in Rome and Florence. Make sure you check train schedules to see how much time will be lost on travel days. Don't forget to include packing/unpacking checking in/checking out of hotels. Some days can become quite short!

No Venice? I personally would take away Cinque Terre and Milan and give those days to Venice. And take a day or two from Siena too. Venice is not a place to go and 'see things'. Venice is the 'thing' itself and you enter into it. Walking out of the train station immediately puts you in a totally different experience. It's different than Rome, Siena, Florence - it's not art in a museum, it's art you wander through. I never spend less than 5 nights in Venice every year for more than a dozen years now. Once you've seen the major sites (ok, there are those), just turn left at the next alley and try to get lost! A whole new appreciation of Venice is there for you to discover.

Assisi is another matter. There is some magnificent art to be found in museums and churches (not just the 3 main ones). Don't forget to discover the ancient Roman ruins under the Piazza Comune. And also the more ancient Etruscan ruins under Santa Maria Maggiore. There's a lot more to Assisi than St. Francis and St. Claire. Assisi is also a wonderful place "to be". Once the tourist groups leave, late in the afternoon, the true benefits of Assisi become available. Go to Santa Chiara (St. Claire) and listen to the cloistered nuns sing evening prayer (6 o'clock). Walk through the city's various levels (remember it's built on the side of a mountain) at dusk and late at night to enjoy the cool evening air and the views. No wonder Francis spoke so much about 'peace'. Full truth: I spent 16 summers in Assisi as part of an international music festival.

Happy planning. I know this site will give you plenty of help and ask you plenty of questions to nurture your dreams. Remember: you deserve this!

hey hey stcar
how fun to be planning your italian vacation. i'll give you couple ideas for a day trip to countryside and smaller villages outside rome. saw a special on TV about this place, saved it, and next trip to rome will plan this.
withlocals.com/beautiful countryside day trip: castelli romani
this is the frascati area known for wine and the pope's summer castel gandolfo
lacucinaitaliana.com/the buxom cookie from frascati
read up about this famous cookie and nonna rosanna, 93 years old, still baking in the ceralli forno a legna. "best pork porchetta", bakery, pizza oven (ceralli.it)
italylife.com/lake nemi and its wild berry
learn about this small village known for it's strawberry and annual festival, the lake and boat museum, and the temple is home to diana, goddess of hunting.
oldfrascati.com
another tour in frascati. short 30 minute train ride from rome. get out of the hustle and bustle, have a relaxing and fun day learning about it plus eating and drinking.
cross-pollinate.com

a website that offers BnB's/apartments within some cities in italy.
have fun with your research and hope some of this may help you decide.
aloha

I read your trip reports for a prior trip to Amalfi and Assisi. Are you going back to Assisi due to more work for your husband or do you just want to see more there?

I have made only one trip to Italy, but it was a long one (3+ weeks). I spent 4 nights in Siena and 3 nights in Florence, which worked well for me and a friend, so I have no problem with your Siena/Florence time, especially since you mentioned wanting to spend some time in smaller places in your prior trip report.

Enjoy Tuscany. You can always include Venice in your next trip to Italy. 🙂

You'll likely want to rent a car for exploring Tuscany. Driving in and out of Siena is not necessarily easy so I'd say do 2 nights there and pick a hill town in Val D'Orcia to stay the other 3. Montepulciano was our favorite. Make sure your lodgings offer easy parking/access no matter which town you chose.

We loved Assisi as well but I think we would have been bored with 3 nights. We stayed 2 and visited Spello one day.

I'd pick Venice any day over CT.

If you do Judy's itinerary suggest you do it in reverse.

Much easier to fly into Venice than out.

Flying into Venice and saving Rome for the last stop will help you absorb its intensity after your relaxing time in Venice. Marco Polo airport is smaller too, compared to Rome.
If you want to give your friends an overall introduction to Italy, Venice is essential as is Florence and Rome. I just came home yesterday from Venice so I feel passionately about it.

Hill towns and the countryside can be better appreciated in contrast when you have seen the major cities.

Thank you everyone, this is exactly what I was looking for. Great ideas and advice. I had heard that we should not bother with Venice, too crowded, expensive, flooding etc. I am glad to hear that it is definitely worth visiting. We will put it back on the list for consideration. Planning this trip will be a lot of fun and I am looking forward to more of your thoughts as our planning gets going.

Thank you again