Hello!

I've been keeping an eye on flights for our September trip to Italy (open jaw Boston to Venice, Rome to Boston. The lowest I have found (with the exception of flights with extremely long layovers) is $1100 per person. Do you think this is a good price? Or, should I wait a bit longer?

It's not a great price, but it is a decent price. And given September is considered still high season in many circles, I'd buy it before it goes up, which it may.

Seems to me to be decent. Prices are very high.

Just purchased open jaw Montana to Venice ,Naples back to Montana in September for $1480 which was down from $1795. I feel it was a good deal, but who knows

I doubt it will go lower. I'd buy it and then stop checking.

Do you think a two hour layover in Dublin is long enough (as long as initial flight is on time)? Do we go through customs and such in Dublin or Italy?

If the ticket is booked as a single booking, and 2 hours is what the give you then I'd say, yes, it's enough time. If you're flying to Ireland on 1 ticket and buying another to Italy, then if it isn't enough, you'll be responsible for buying another onward ticket. In the first instance, if the airline issues the ticket, Boston to Italy in 2 legs, they're responsible for getting you there, no additional charge if you don't make the 2nd flight.

It is one airline and purchase, thank you!

On the other hand, if it is a busy time of year, there is no telling when there will be space on another flight. But since Ireland is not in Schengen and Italy is I would expect you will stay airside.