How far in advance to book train tickets and other sights

This is just my opinion. I imagine you'll get a different perspective from lots of people

Regional trains are frequent so you probably don't need to worry about missing out. You can book a month ahead which guarantees you the lowest price, but then you have to travel that day. Alternatively, you can book online a few days before or even at the station if you want some flexibility. That's what I tend to do unless I have a "mission-critical" travel thing like I need to be somewhere to catch a flight.

There are competing train companies in Italy - Trenitalia and Italo. Both are equally good so pick the one that fits your schedule.

Museums - It sucks but these days, the most popular museums e.g the Uffizi should be booked as early as possible. Alternatively, it seems like you can always find tours with ticket included the day before or even same day. It costs more but you get a guided tour and again, you get that flexibility.

You do not need to reserve/pre-purchase tickets for regional trains. These are essentially commuter trains that run regularly and do not have reserved seating. They never technically sell out. Download the Trenitalia app on your phone and familiarize yourself on how to buy tickets. You can also buy tickets at the train station from Trenitalia machines.

https://www.seat61.com/train-travel-in-italy.htm

As for museums, some require advanced reservations. It’s always recommended to buy directly from the museum’s website.

The suggestions about booking museums and other popular sights ASAP is excellent (and even essential), although note that many of the official Websites only release tickets for dates a little at a time. So even if you already know the dates for which you want tickets, those dates might not be released until sometime in the future, and you’ll need to monitor those Websites regularly to determine when your dates are being offered.

Don’t get suckered into tickets from a third-party tour company Website. And, unfortunately, many of those companies seem to snatch up tickets immediately after they go on sale (they must have super-fast computers), then scalp them at higher prices after a museum or sight is “sold out.” There may be cases where you’ll need to be at your computer at midnight Italian Time the day that your desired tickets go on sale, and start clicking, to score your tickets before Viatour, Get Your Guide, and other third-party resellers buy them all up. This includes many popular sights around Florence and Rome, but could include Northern Italy places, too. Are you planning on seeing the Last Supper in Milan?

Thanks for information about trains. Maybe I misunderstood from what I read in a guide book- I had the impression that the regional trains were run by Trenitalia and that the high speed intercity trains between major cities tended to be run by Italo.

I will play around with the train apps.

I will start researching out how far in advance museums release tickets so I can be prepared so that I get them for my preferred dates.

I have no plans to see The Last Supper. I know from previous European trips that by the end of the trip my interest in churches and religious art have greatly diminished compared to the start of the trip. In Milan, the Duomo - inside and the roof top ticket will be enough.

Trenitalia runs regional trains and fast trans- this is the official state train company

ItaloTreno runs only fast trains on select routes- this is a private company

Regional tickets never need to be purchased in advance- the price never changes and they can’t sell out- no reserved seats

I find it easier to look at train routes on Google Maps and then go to the apps. Remember that the day of the week and the time makes a difference, like, one train takes 4 hours with a change while another going between the same two places takes 1.5 hours with no changes.

There really aren't that many sights in Italy that need to be prebooked. If you're traveling rapidly and planning to see only the most famous places in each city, it could be that you'll need to buy quite a few tickets ahead of time, but do not assume that all should be purchased as soon as tickets become available. Remember that sightseeing tickets are usually not changeable or refundable. It's financially risky to have a lot of money tied up in sightseeing tickets purchased long before a trip.

Tell us what sights you want to see and we'll try to tell you where to focus your early ticket-purchasing efforts.

I've updated my original post with sites I want to see that need tickets.

The venues that I would have tickets for in advance:

Venice San Marco church and museum and Campanile Doges's palace?

Padua Scrovegni Chapel and associated museum - I know this needs to be
booked ASAP for tickets on one of my two days I am in Podavo

You can't purchase until they are available which is probably not for a while

Ravenna

We bought our tickets online a week or so before our trip.

Milan
Duomo and roof top tour
Armani Silos - I've looked at the website

Start gathering the official websites for all these venues- if you are not sure what is official ask here.

I'd be very surprised if the Armani Silos needs to be booked in advance, but I haven't been there; it was closed during the time I was in Milan in 2024. Sometimes special exhibitions at not-heavily-visited museums are highly popular and can sell out.

At the end of August 2024, a travel mate and I just walked into the Duomo ticket office and purchased tickets for essentially immediate entry. She wanted to do the rooftop tour; I, having already done that, only bought a ticket for the interior. I don't think there's any mad rush to get Duomo tickets, but if you absolutely have to go at a specific time--especially if you need the first entry time of the day, which may be popular with tour groups, that could change things.

We also basically walked right up and bought the Ravenna combo ticket for immediate entry to the timed mosaic sites; that was in early September 2022. I've been to Ravenna twice (first time in the summer of 2015) and never seen it crowded, but I know it can be a lot busier than what I've observed--perhaps especially in the spring when schools are doing field trips.

The Scrovegni Chapel was not selling out very early on my two visits (2015 and 2022). I just bought the sightseeing card at the tourist office and got a reservation for the next day. However, I was spending 3 nights in Padua and had a flexible schedule. I wouldn't recommend a daytripper arrive in town without a reservation, but I also doubt that it's necessary to grab a ticket as soon as they go on sale.

San Marco allows online purchase of entry tickets, but the quantity available is not large. Everyone without one of those tickets needs to queue; fortunately, the (usually long) queue moves rather fast. Still, it's obviously better not to have to deal with that at all, so grabbing an entry ticket is smart, and it probably does require quick action after the tickets go on sale. I don't know anything about ticketing for the Campanile.

I don't think the Guggenheim sells out very early, but I've observed lines at the ticket office, and when I've bought online tickets a day or two ahead of time, not all the time blocks were available. If you have limited time in Venice and need to hit the Guggenheim at a specific time, you'd be smart to buy a little earlier than I do. Expect the museum to be crowded.

The Accademia in Venice has been very lightly visited on my two recent trips. Unless there's a high-profile special exhibition, I doubt you'll have an issue there, though there's always a possibility tour groups might grab a bunch of tickets for specific entry times (most likely early in the morning).

I haven't been to the Doge's Palace and don't know anything about ticketing urgency there. However, the Secret Itineraries Tour is very popular on this forum, and it wouldn't surprise me if that tour sells out ahead of time when general-entry tickets are still available.

Rather than locking in all of the places you've listed, I'd monitor their websites in the month or so leading up to the trip to see how early entry times are selling out.

I spent a month touring Italy by train last September. I purchased all of my train tickets, even for regional trains, before I left. Most of the time, I was glad I did that but, quite a few times, I found my train had been cancelled due to a rail strike or whatever. I've never had this happen so often in any other country in Europe. It's not so easy to get a refund, however the cost of most of the tickets was so low, it really didn't matter. I didn't even bother to make a claim with my travel insurance company. The lines for tickets at machines and at windows was often so long, that I think if I had to do it over again, I would do the same. I like to sleep as late as possible in the morning, so I didn't want to have to get to the station super early to buy a ticket. I was also worried about pickpockets and scammers who hang out by the ticket machines to "help" people. I mostly used Trainline for buying tickets but sometimes I used Trenitalia.
Looking at your list, I booked the Accademia and Doge's Palace in Venice ahead. I also booked the Milan Duomo and Rooftop ahead. The rooftop was great. I very much enjoyed Rick's audio tour of the rooftop, but much preferred the self-guided tour in his Italy book for the interior.
Have a great trip.

Thanks for the more recent replies.

Other than Ravenna which will be a day trip from Bologna, all my stay are 3 or 4 nights so I have flexibility of choosing between 2 or 3 dates for sites at most of the cities. I suspect there were fewer travelers in post pandemic 2022 compared to now.

It sounds like I can buy my train tickets a day or two in advance and same for most places I will visit. I would rather have tickets in advance as much as possible to minimize lines ups, fumbling with unfamiliar machines in a train station etc.

Tickets for non-regional trains can be substantially cheaper if purchased in advance.

Get the Trenitalia app
Very easy to use and very handy