How far in advance should you book flights and rooms for 2 week italy trip ?

Rooms as soon as you can if they have a teaspnable cancellation policy. Watch flights and prices. If booking far out, expect your flight times to change.

Suki is right. If you are getting a villa or agritourismo the further out the better as they can book quickly, especially the ones you prefer. If you can afford it reserve refundable airline tickets, then you have no worries. Consider travel insurance as well. Once you lay down cash it is nice to have some way of getting some of it back if necessary.

Flight: I usually pick a price point, then start watching six months out, usually have purchased by 3 months out.

Hotel: First you would need a firm itinerary. I usually book First stop and last stop, since those are set after you get tickets, then book as things firm up. It also depends on where you are going and if you want to stay someplace special, time of year, what is going on...etc. In high demand areas, earlier the better, other areas...it can wait. On a given trip, I usually will not book all nights ahead, leaving a few open for flexibility, just booking the highlights.

I will add that I do not support the practice of booking multiple rooms or overlapping bookings then cancelling as my plans firm up. Most of the places I stay are smaller and I find it rude and inconsiderate to jerk the owners around and possibly have them lose out on a booking from other travelers trying to get a room. Not saying that people on this board would do that, but I have seen that advice given in various forums.

I agree, book your hotel as soon as you can and make sure they have a cancellation policy. Watch the flights and see how much it is and since you may be booking a non refundable ticket, keep in mind there is a stiff penalty to change flights or cancel. Once you are definite on your dates and know you are going, book the flights.

I know that you did not ask this but, also keep in mind that not only do you need hotels and flights, you need to make reservations for museums and some churches. You don't say where in Italy you are planning to go but examples are:
Vatican, make the reservation as soon as they allow you to do so, given your dates, the Borghese Gallery in Rome, the Last Supper in Milan also needs a reservation as well as the Uffizi Gallery in Florence and the Academia ( to see the David) in Florence. Make sure you get the RS guide books or book to see where you need to make reservations. Never to early to plan your trip to Italy because you need to know what you want to see and do and once you start going on the museum websites they will tell you when you can book your reservations. To insure that you get to see the museums and Vatican on your trip and not be disappointed that you could not get in if you wait until the last minute or when you get to Italy.

Have a great time.

I use Kayak to start watching flights as soon as I know when I'm going and I have a rough amount of what I hope to pay in my head. Watch the fares for a little while to get a sense of how they change. I have found that about six months out there is often a good price, meaning equal to or below what I hope to pay. I book it then and don't look back.
Cynthia

We always get apartments so we book that first and as early as possible then we monitor air fares and buy when it seems reasonable fairly far in advance - usually about 3 mos out. If you book air first you can be more flexible on getting a good air fare and then book hotels. But good hotels and apartments book up far in advance.

We start looking at flights about 7 or 8 months out. We get a sense of which flights we would like and follow them. When the price is good for us, we buy. We then start to jump on lodging. Usually about 5 or 6 months out.

You can start to see flights when you are 11 months out. I used to think the best rates would be available if you're in a position to book right away when the flights are available, but haven't found this to be true. I have used Hopper, an Apple App. You put in your cities and dates and ask it to watch for flights for you. The app will tell you the best rate for the itinerary, and let you shop for flights, but it will also give you a prediction as to how much lower it might go if you wait. It gives you alerts when there is a rate you might want to consider. Delta is not on Hopper, but its international partners (KLM, Air France, Alitalia) are. Before discovering Hopper, my practice was that as soon as I knew my dates and cities, I'd use a multi-airline search engine (typically Expedia) to check airfare once a day. I know, that may be a little obsessive, but it only takes a couple minutes. For my upcoming trip to Italy, my once-per-day check allowed me to jump on a $871 RT rate for a non-stop between Chicago and Rome. During peak season. I was pretty happy with that rate! The prior day, the flight had been about $1,000 more. The $871 rate only stuck around for a couple days. My obsession with daily checking paid off. That flight was booked on election day, Nov. 8. The trip is next week.

Flights swing all over the place and my reading of flight price optimization theories is that there really isn't a perfect optimum strategy. The price of a seat on a plane can vary based on the day of the week and even the hours within that day.

Nevertheless 6-22 weeks ahead of departure (yes, I realize that's anywhere from 1.5 to 3.5 months) has the best shot at the best price. Better to fly Tuesday through Thursday and on Saturday. Buy day is anyone's guess but time of day should either be the middle of the night or I'd guess during early work hours. Avoid lunch hour and dinner hours.

Hotels don't have as much flux.

I booked our latest tickets 9 months out because that is when I found tickets at a good price point. I recommend using Google Flights as your search engine. With the calendar view you can easily see prices 11 months out. I use that to gauge what the lowest reasonable fare I can expect between my city and my chosen destination regardless of the time of year. Then I use Google's tracking function to watch for price changes and book as soon as my chosen dates appear at that low price point I previously identified (assuming they ever do). I check frequently, much like others have mentioned.

We bought our plane tickets back in September for our trip next week. We paid 1400 for two on American R/T from San Francisco to Venice. It was a crazy good deal. We did end up making several tweaks to our itinerary since it was so far off. (Had plenty of opportunity to do more research).
I just kept looking at Expedia and other travel sites. Can't wait till next Saturday. The Valgardena, Varenna and Venice here we come 😎.

Hi Julipok2
What parts of italy are you planning to go to? I have used kayak, fareboom, airfarewatchdog, and bookairfare.com. Looked at airfare, times (departing, stops, how long layovers are, arrivals). Put alerts out for our multicity flight this september. (sfo-venice-ams-sfo). Found a flight with british airlines for $900 on fareboom.com and booked end of april, which was $1700 same flight on BA website. Used booking.com for 2 bedroom apartment (4nights) in venice for $690, tripadvisor vacation rental paris (5 nights) $1200 and houseboathotel in amsterdam for $1000 (4 nights). With 4 adults traveling, did lots of research, time consuming, but it all fell into place. Used trainline.eu for train travel with great fares. Also doing a private taxi out of venice to tour the prosecco road. Can't wait, hurry up September!!! LOL Hey Richard, you're my next door neighbor here in California. GO WARRIORS!! Have a great vacation
ALOHA
Princess Pupule

OK, this won't work for most people, but we're retired so there are no restrictions on timing (no need to get vacation time approved in advance, nobody in school) so when I see an incredible bargain I jump on it -- and then tell my husband "we're going to Italy next May."

Hotels usually booked shortly after plane fare -- with cancellable reservations.