9 Night Italy Itinerary Advice

I have advice only for your first two questions.

1. Our preferred location in Rome is the Prato district (near Hadrians tomb). Most of the major sites are within easy walking distance and there are few tourists.

2. There is a high-speed train from Rome to Florence. No need to book far in advance. The district we like is the Oltrano (near the Pitti Place). Far fewer tourists and many nice restaurants. It is an easy walk across the Arno from there to Florence's major tourist attractions.

We have stayed in AirB&B's in both cities with positive results.

Enjoy.

I don’t see any need for a car
Would be more of a headache than a help

2 nights in Milan is fine
Get your Last Supper tickets as soon as available if you are interested

The Duomo and Roof terraces are worth a visit

We stayed close to Duomo at Duca Di York hotel

Thanks for the feedback! I understand the train from Florence to Levanto (going there to visit Cinque Terre) can be quite crowded too, plus there's the stopover in Pisa to worry about. Is there a round trip bus service perhaps, or other ideas how to make the journey? I guess in this scenario we would actually go back to Florence for the train to Milan, right?

For train routes, go to the Trenitalia website. Input your start and end points and pick a date a few weeks from now that is the same day of the week you want to travel (its likely too early to book tickets)l. Be sure to use the proper Italian names (Roma, Firenze, Milano). Clicking on any train option listed will expand to show where any connections are and how long each connection is. It's really not that complicated once you get used to it. A quick glance looks like a train change in either Pisa or La Sezia to get to Levanto, and 2 changes - in Genoa and somewhere else (not Florence) to get to Milan from Levanto.

To learn more about European train travel, explore the Man in Seat 61 website. It's a goldmine if useful information.

Really, rental cars in Italy need to be reserved for rural travel that lacks any public transportation. In your case a car would be more trouble than it's worth.

guess in this scenario we would actually go back to Florence for the
train to Milan, right?

No, there are some trains which can get you from Levanto to Milano Centrale in abt.. 3 hours, no changes.
Explore your options on the Trenitalia website..

Changing trains in Pisa Centrale (we've been through that station) en route from Florence (Firenze S.M. Novella) to Levanto is no big deal, and often enough bus stops are not as conveniently located as train stations even if there is a direct bus (I'm not seeing one but didn't dig too deep). It's also likely to take longer.

We like the Aventine area of Rome. It is a quiet leafy area. We stayed in a hotel so I can't recommend any Airbnb's.

Booking fast trains - Rome to Florence, Florence to Milan -come with assigned seats and specific times. So you trade price by buying a discount ticket early versus flexibility because you have to take that train. Super discount tickets come with no changes and as the price rises so does the flexibility.

The state train company runs most local regionale trains and will book through tickets mixing fast a local trains as needed.
https://www.trenitalia.com/en.html they also have a phone app you should get that has schedules, buy tickets and more. Use the Italian names for cities "Firenze" for Florence for best results.

There is a private fast train company .Italo also offers fast trains but only fast trains nothing local. The trains and service are pretty similar and if you're only moving between big cities they are worth checking.
https://www.italotreno.it/en
Any other site is a 3rd party reseller. Fine to check times but I would always check with the source for full schedules.

I wouldn't rent a car unless you really need it to reach your AirBnB. Coastal driving in August has much less romance to it than you imagine and the parking even less so. Levanto has ferries and very short train hops to CT towns.
I don't recommend driving in large Italian cities for anyone attached to their sanity.

Have a great trip,
=Tod

Keep in mind that August in Italy is their vacation month, and every beach or ocean-side location will be heaving with Italians on vacation, and some restaurants will actually be closed because their staff is on vacation. Especially because your vacation is nine days (or nights?), really consider whether you want to make a trip to Levanto / the Cinque Terre in August. Also, it's a bit of a hassle to get there, so out of your nine days, do you want to spend that much time traveling to get there.

I also suggest that for this trip the way it's currently planned, you don't need to rent a car. In terms of when to purchase tickets, for longer trips that would be on a high-speed train, I tend to buy them as soon as tickets are available; I think that's usually 90 days out.

For the different places for which you're considering a two-night stay, whether that will suffice for you will depend on your interests. For me (for example), I love fine art and sculpture, and you'll be in three cities that have A LOT of that. So for me, two nights would not be enough. And if anyone in your group is interested in ancient Rome, you could spend your entire vacation in Rome! So to decide if your allotted days is enough for your group, make a list of the things and places you want to see in that location, then decide.

The thing about touristy areas, those same areas also tend to be closer to the places that visitors like to visit. When in Rome, we have mostly stayed very close to Piazza Navona. That way, we can easily walk to that Piazza, or Campo d'Fiori, or the Pantheon, to sit at a cafe and people-watch. It's also easier for us to then get to all of the other sites we want to visit.

In Florence, I like to stay nearish the Uffizi and the River; we really enjoyed staying at B&B La Casa dei Tintori, but it sounds like you prefer AirBnBs. I have some moral issues with the effect that AirBnBs have on cities and affordability, so stay in B&Bs or hotels.

In Milan, I like to stay near the Cathedral for the same reason. And there are many places near there for cafe people-watching. Another interesting part of the city to stay in is Brera.

So, generally speaking, for nine days/nights, you are considering a number of two-night stays. That only gives you one full day in any such location, and you will be packing/unpacking and moving and getting yourself to and from your selected form of transportation just about every other day. Consider whether you would, instead, want to slow down your vacation time a little by eliminating some destinations, and have more time to wander the city streets, admire the beauty, and people-watch while at cafes.

These are all great tips, and wonderful food for thought - thanks to everyone so much! I can see how eliminating the rental car can be beneficial for this particular itinerary. The only problem is the leg from Florence to Levanto which is very long with most trains requiring 2 transfers. Is there any idea how much a private driver would charge for this run on a Sunday morning / midday in late August?

The only problem is the leg from Florence to Levanto which is very
long with most trains requiring 2 transfers.

As said above, changing trains is not a big deal, and there are plenty of trains between Florence and Levanto that only require ONE change: see the Trenitalia website. It's a journey of 3 hours + some odd minutes: not "very" long. It's not a "problem". A first estimate for a driver on a random day for 4 people on Daytrip (a recommended resource from other posters) came up with an estimate of €595 for this trip. Ouch.

Take the train. It's really not hard.
The only thing I'd look at s how to validate pre-purchased e-tickets if either or both legs involve a regionale train. If you purchase paper tickets at the station, you just time-stamp them in the machines near the tracks before boarding.

There is a train from Florence to Levanto that requires one transfer. Take the regionale from Florence to Pisa, then take the Intercity train from Pisa to Levnto. Actually this Intercity train's final destination is Milan.

Take the same Intercity train from Levanto to Milan, no transfer needed.

Changing trains is no big deal when you have done it a time or two but it can be stress inducing for first timers. My suggestion is to search Youtube for videos or just keep asking questions here.

Four key points: Make sure you minimize luggage. You DO NOT want a big, shared suitcase. EAch of you should take a small bag that you can carry up and down stairs as your train connections may have you going up and down stairs. You also need to be able to carry the bag onto the train.

As mentioned above, make sure if you buy paper tickets that you validate the ticket in the machine. The machines may be on the platform or in the station and look like a ticket dispensing machine.

Beware of folks offering to help you carry your bag to the train or who offer to help load it onto the train. They will expect money in return.

Search this site for info on keeping your valuables safe. Pickpockets are real professionals in highly touristed areas.

Frankly, I would enjoy the beach in Levanto and skip the CT. By then the heat and crowds may convince you to do just that.

Thanks to everyone for their advice! So, in the end, we decided to bypass the Italian Riviera and do more of a highlights itinerary: 3 nights each in Rome, Florence, and Milan. For Milan, we're looking for similar advice as to what part of town to look for an Airbnb in. We like districts with less tourists, local restaurants, and public transportation journeys to the main sites within a reasonable amount of time. If the area is walkable to certain sites, even better.

Lastly, and advice on how to best beat the heat and make the most of our short 9 night stay in August would be great. If there are sites we must book far in advance, please advise.

One thing we implemented in Spain last August that worked well as to do our inter-city train journeys in the early afternoon. I found the advanced purchase tickets in Spain were the least expensive during those timeframes, and it kept us out of the sun during the hottest part of the day. Planing to do the same in Italy this coming Summer!

If there are sites we must book far in advance, please advise:

Do you have a list of attractions you are planning to visit?
There are umpty threads on that subject here on the forums if you do a search but...

Rome:
Colosseum: I'll recommend a morning tour that includes that one + the Palatine and Forum. The official ticket seller (currently Coopculture but is supposed to change on May 1) doesn't offer that option but we can steer you to some companies that do if interested. The latter two sites are much more complex and really benefit from a guide. Tours are generally abt. 3-4 hours in length.
The colosseum is the most-visited attraction in all of Italy and the scramble for high-season tickets of the Coopculture site is fierce: another reason to look at a more inclusive tour.

Vatican Museums: tickets/tours book abt. 60 days in advance on the Vatican's website.

Florence:
Uffizi
Dome climb of Santa Maria del Fiore (duomo)
Brancacci Chapel
I would probably reserve for the Accademia too.

Milan:
Last Supper/Santa Maria delle Grazie