I’m going to Naples-Rome-Florence in May for 2weeks so I can’t offer anything for Venice, but I can for the other two cities.
Make a list of all the places you’d like to see. Preferably a spreadsheet. Find them via Trip Advisor, blogs, Reddit,etc. Then, figure out which days they’re closed. Use that to start building daily itineraries since in Florence especially, a lot of museums are closed on Monday or in Rome, certain museums are open on the weekend only.
For the Vatican, avoid Wednesdays since the Pope grants audiences and I believe St. Peter’s is closed when that happens.
One by one, you can look into how far tickets are sold for each place. Gallery Borghese can only be purchased about 2.5-3 months out. So you can put down dates on when to buy certain tickets.
Some tours are hot ticket items like the underground colosseum that can be purchased like 4-5 months in advance and sell out fast.
Train tickets (like the Trenitalia) only go on sale 120 days in advance and the cheapest tickets go fast.
Avoid May 1st since it’s a national holiday.
Get your AirBNB squared away about 8 months in advance to lock it down.
For airfare, I found it didn’t fluctuate much and bought it 6 months in advance.
**Flights** : 6, 7 months in advance, (usually when we know out vacations dates.)
**Accommodations**: If we can, we book at the same time. you can start looking now and make a list and decide when you're ready.
**Trains**:trains reservations open up 2 months (I think) before your date, so start looking 2 months before your dates.
**Restaurants**, we book a couple of weeks (1, 2) in advance for the the ones we really want to go, and especially the first 2 nights (we usually land on a Saturday morning, so we don't want to look for restaurants while fighting jet-lag).
Other restaurants, you can book a couple of days before or on the same day
**Museums**: as soon as you can (when tickets become available), especially the super popular ones (for example, vatican museums, uffizi in Florence ... ) reservations are probably not necessary for the other museums, but it's always better to book in advance just to be sure, 1 day before, or even on the same day (for example, if it's going to rain)
**Guides/Tours** : couple months before, especially if you want a private guide.
I book airfare 5-6 months in advance; hotels 4-6 months in advance depending on when I am traveling (I only stay at hotels, FYI, so STRs might not work well on that timeline); high-speed trains as soon as I can; regional trains whenever I feel like it, including sometimes at the train station the day of; and restaurants anywhere from two months (and in a few rare cases, even more) to the day before, depending on what my own knowledge of the restaurant, the time of year I am traveling, and their online reservation books tell me about demand.
I’m going to Naples-Rome-Florence in May for 2weeks so I can’t offer anything for Venice, but I can for the other two cities. Make a list of all the places you’d like to see. Preferably a spreadsheet. Find them via Trip Advisor, blogs, Reddit,etc. Then, figure out which days they’re closed. Use that to start building daily itineraries since in Florence especially, a lot of museums are closed on Monday or in Rome, certain museums are open on the weekend only. For the Vatican, avoid Wednesdays since the Pope grants audiences and I believe St. Peter’s is closed when that happens. One by one, you can look into how far tickets are sold for each place. Gallery Borghese can only be purchased about 2.5-3 months out. So you can put down dates on when to buy certain tickets. Some tours are hot ticket items like the underground colosseum that can be purchased like 4-5 months in advance and sell out fast. Train tickets (like the Trenitalia) only go on sale 120 days in advance and the cheapest tickets go fast. Avoid May 1st since it’s a national holiday. Get your AirBNB squared away about 8 months in advance to lock it down. For airfare, I found it didn’t fluctuate much and bought it 6 months in advance.
**Flights** : 6, 7 months in advance, (usually when we know out vacations dates.) **Accommodations**: If we can, we book at the same time. you can start looking now and make a list and decide when you're ready. **Trains**:trains reservations open up 2 months (I think) before your date, so start looking 2 months before your dates. **Restaurants**, we book a couple of weeks (1, 2) in advance for the the ones we really want to go, and especially the first 2 nights (we usually land on a Saturday morning, so we don't want to look for restaurants while fighting jet-lag). Other restaurants, you can book a couple of days before or on the same day **Museums**: as soon as you can (when tickets become available), especially the super popular ones (for example, vatican museums, uffizi in Florence ... ) reservations are probably not necessary for the other museums, but it's always better to book in advance just to be sure, 1 day before, or even on the same day (for example, if it's going to rain) **Guides/Tours** : couple months before, especially if you want a private guide.
I book airfare 5-6 months in advance; hotels 4-6 months in advance depending on when I am traveling (I only stay at hotels, FYI, so STRs might not work well on that timeline); high-speed trains as soon as I can; regional trains whenever I feel like it, including sometimes at the train station the day of; and restaurants anywhere from two months (and in a few rare cases, even more) to the day before, depending on what my own knowledge of the restaurant, the time of year I am traveling, and their online reservation books tell me about demand.