Timing questions for trip to Italy

Carolina,
I have had the opportunity to visit Italy many times. Never have I booked accommodations first. You will always have more room options and less flight options. Definitely book your flight first.
Have fun

Lorieann

We booked our apartments over a year ago for a trip this fall and bought airline tix in March. So many flights from US to Italy that you should have no problem syncing everything, IMO. We're flying into Venice and out of Rome.

I would pin down the flights first but if there was someplace special that you really wanted then I would book it and just be flexible the days before and after.

It's already mid-May. Now is the time to get the best deals on rooms. Just make sure of the cancellation policies before you commit. How much can your dates vary? If it's 2-3 days one way or the other, you can book overlapping dates if you find a really good bargain and then shorten your stay (within the cancellation time).

Don't be "penny-wise." How much can you save on the flights - and how long will you wait? How much more can the rooms cost if you wait. Early September is still high season in Italy (maybe all of September), so there's more competition for rooms.

It's pretty common to see significant price discrepancies within a single week, as well as price differences for different destinations. Milan can be quite a bit cheaper than Venice, for example. I would always book the flights first unless there was a single hotel that was a trip-maker for me.

If your trip is only 3-4 months away I sure would not be waiting, best rooms/hotels are already filled I would suspect.

Unrelated to the specific time in this case:
I would normally at least identify which flights I want to take. Even better if you see more than 1 option on the flight that could work. If the flight is not full at all when looking at available seats and I think the flight cost will drop ; I would not have a problem booking hotels first and then the flight weeks/months later but would keep my eye on those seats.
If you can book some of the hotels with a free cancellation that will make you feel much more comfortable about booking the hotels first and the flight later. On many sites it is about a 10% premium for booking with free cancellation but then also allows you to pay at checkout rather than months in advance.

I was actually disappointed how few direct flights from the US to Italy there are (the number of options has been decreasing over the past 5 years plus not increasing) and how the prices are higher compared to other European destinations of similar distance. For Italy your cheapest options are usually flying elsewhere in Europe first and then taking a low cost intra-Europe flight to Italy as those are plentiful.

Flight first. You may find a flash sale that is say $500 cheaper to fly into Rome and decide to do that.