Tuscany and/or Assisi

Guerino - you don't tell us when you will be travelling so answers won't be too specific and maybe a little helpful. But I know all of us will be there for you!

4 nights in Venice is a good start. There's much to do there, much to see, much to experience. It's a magical place, a bit of time travel.

A day trip from Florence to Siena, I would highly recommend. I'd recommend taking the bus rather than the train - it's more scenic and much more convenient. There's plenty to do there including wandering around the neighborhoods. The museums and the Duomo are well worthwhile - and I'm not a big museum fan.

Why are you going to Cinque Terre? That's an honest question especially since you are giving it so much time. Lucca would be worth some time.

Assisi is one of my favorite places. The lower area around the Basilica San Francesco is touristy for sure but keep climbing and a very interesting and peaceful medieval city quickly appears. The area around the Piazza Comune would be (and has been for many years) my choice for a home base. I spent 2 weeks every year for 16 years there as a singer with an international music festival. Assisi at night is an experience not to be missed!

Give your extra nights (if you cut time from Cinque Terre) to Rome. There's always a reason to stay longer in Rome! Oh, and forget the car! Trains and buses are so much easier.

Are you flying into Venice and out of Rome?

As noted, CT is probably not worth 4 nights. Tuscany usually is, although it depends on your personal desires - for example, if food, frescoes, wine, etc. are of interest. Tuscany is one place where a car is a net benefit. But easy parking at your hotel is important. It seems clear that you are early in your research, since you likely would not daytrip to Siena from Florence if you were going to stay in Tuscany. Note that total travel time is important because there is so much to do and see in Siena.

I have not been to Pisa, but I note that you're not interested in Milan. I guess it's much easier to fly into Venice today, than when we had to fly into Milan and train to Venice. I'm glad to have seen the Last Supper, despite its poor condition.

I strongly recommend that you use the Search box top center to learn from vast numbers of discussions on this board regarding both Tuscany and car rentals in Italy. Obviously a car is useless in Rome or Venice. Some posters here have been pleased to have a car in Florence, but I personally would not. Again, I'd make sure that you have a strong interest in Renaissance art before staying more than 3 nights in Florence. (I've been there twice.)

Heat and sun are important in Tuscany in the summer. We are not pool-people, but we loved the pool at our rural hotel after a sweltering day of touring in an air-conditioned car. We generally only book a/c hotels in the summer.

We will travel in June 2023 (never dreaming, always planning). Flying into Venice and out of Rome. We are a family of 4 with 2 teenagers. I am all about history, art and music. The teens, shopping and scenery. The wife is into everything Italian. I have thought of cutting a night from CT to stay in Siena/Volterra area and Assisi. Milan will be saved for another trip.

Guerino, try to fit Assisi in.

In the General Europe forum there is a thread, when the day trippers leave. Assisi is one of those places that totally changes when all the tourist leave.

I would take a day away from the Cinque Terre and add it Florence/ Tuscany.

We were in Italy this past September/October, including parts of Tuscany, Umbria, and the Cinque Terre. Based on this latest trip, I’d say see more Tuscany, plus Orvieto in southwestern Umbria. It’s on your way to Rome, in addition to being a very worthwhile visit. See it especially earlier and later, before the 11AM crowds arrive, and after they leave at 4PM. It’s one of many highlight hill towns in Tuscany.

Assisi had some bright spots, although it was frustrating in a lot of ways, and definitely not the favorite part of the trip. Getting buzzed by traffic was unnerving, and it was the least pedestrian-friendly town the whole trip - including Rome! If you’re seeking it for spiritual reasons, maybe it’s a must-do, but I’d really pick Tuscan locations over Assisi.

Cinque was our second time there, after the first one in June 2001. Frankly, it was disappointing in some ways, compared with 20 years ago. Way more crowded now, and while there were outstanding restaurants and gelato places (definitely go to Gelateria Alberto in Corniglia!), others were a let-down. Maybe June is still a better time to go. The overall vibe 2 months ago was decidedly less welcoming. In addition, recent storms had closed some hiking trails for an undetermined time, which put everybody on just a couple paths. Some hikers weren’t good about sharing the limited trail spaces, and it seemed like being in a subway at rush hour. Being pushing and elbowed wasn’t a fantastic vacation atmosphere. Maybe go to the 5 Terre at least once in your life, but we might not be going back again.

Tuscany is a very large and varied region. Besides Florence and Siena, there are numerous smaller cities and towns which merit visits. The attractions range from seaside to mountains, to wine country, medieval towns and and Etruscan ruins. An incredible number of works by the world’s best known artists are to be found there, and not just in Florence. What I’m saying is that 2 nights (1.5 days?) is not enough even for a taste. I suggest that you identify what you want to do and see in Tuscany, then allot the number of days.

My bias would be to eliminate the Cinque Terre. Some people don’t like Pisa, but I think the Field of Miracles is, well, pretty miraculous, not just the tower, but the cathedral and baptistery. A half day is sufficient. Lucca is also a good choice.
If you are driving, keep in mind that roads are narrow and winding. It may take an hour to get to a place 25 miles away. Otoh, public transportation isn’t much geared toward tourists. We’ve always had a car in Tuscany.

With 16 nights here’s an idea:
Venice – three nights
Florence – three nights
Siena – two nights with a day trip to Montepulciano by direct train (1h 15m).
Tuscany – three nights. Rent a car and drive to Volterra (1h 30m) and then to Pisa (1h 30m) and drop off car. Sleep in Pisa for three nights and take a direct train to Lucca for the day (30-minutes).
Cinque Terre – two nights. Take a direct train from Pisa to Monterosso (1h 15m). Add a day for each day you hike. Take a train to Rome (4h 45m).
Rome – three days

Thanks to all for insights