just how last minute can an Italian trip happen??

You can do it. Shortest trip we did was 4 days of advance planning. The internet makes it easy. Need to be a little flexible as not all hotels may be available and maybe a little more expensive. Start putting it together tonight. Could have it wrapped up by Saturday.

If you don't expect maximum charm and comfort at a bargain price and can be flexible about cities to be visited if you hit a lodging brick wall in the form of a special event that has sucked up all available rooms, I don't see why you can't do what you're considering. Plenty of us travel to Europe, including Italy, and make reservations as we go. I have no clue what you'll face on the airfare front, however. The recent fare sales have probably filled a lot of seats on September flights.

I fly back and forth to the US quite often and rarely book any trip further out than one month. Europe is a flight away, just a few hours longer than if you flew California to New York. It's possible you may not get your first choice hotel but you'll definitely find one. Airfares will not always be higher because the trip is close. There are low fares that come up frequently. View Google flights to see what the fares are for the month of September. September is a quieter month in Europe compared to the summer months. Carpe diem.

So, is it even feasible to get airline tickets/lodging in August for a mid September trip?

Of course! I don't call 4 weeks particularly last minute. I wouldn't hesitate. I find it odd that I am presently planning a trip that is 9 months away...

Give me 45 minutes...on my way! The only limiting factor is $$$$

I'd just like to add that old adage...."nothing ventured, nothing gained". Give it a try!

I'd say go for it!! It's amazing what can come together in just a few short weeks. Check overnight availability, flights, and the rest will all just come together.

Some of our most amazing trips have been with less than two weeks' of planning.

I saw a bumper sticker years ago that wisely advised: DON'T POSTPONE JOY!

I would choose October over September anyway - not as many tourists, not as hot, maybe fall colors in Umbria.

I'd start planning now. You can plan your itinerary, maybe you even have it in a drawer from earlier this year. You can research lodgings, and even book them, just make sure of the cancellation policies; same for a car, if that's in the plan.

I agree with Chani a for a sort vacation I would pick cooler months, October sounds Ideal. I am just back from Italy it was spectacular, but busy and extremely hot especially Florence.

When my dad passed away I went to Florence from San Francisco the same day. So not even 24 h notice. The irony was I had just come back from 3 weeks in Italy the day before. So I traveled from Italy to California and back within 24 hours. The only silver lining in that nightmare was that I didn't have to adjust to the time zone.

On another of my numerous flights I was next to a guy who was flying to Morocco (via Paris) also to see his dying mother. He told me he didn't even bother to buy the ticket ahead of time. He rushed straight to the SFO airport without a ticket and bought it at the counter when he walked in.

Other than the exorbitant price, to me the only limiting factor in traveling last minute is the traffic to get to the airport.

Very doable; we planned a trip to Paris in less than 30 days. In my corporate life I determined that I had a 5 days of carryover vacation that needed to used. The only caveat is whether or not you make reservations that can be cancelled; again from other posters it is a matter of $$$.

Carolina,

Another vote for traveling in October or at the very end of September.

As others have mentioned, you may want to start booking your hotels now.
Just make sure you choose the, "free cancellation option", & that way you've got nothing to lose.

I hope your mom & your DH's dad continue in their "amazing selves" status, so you can make your dream a reality :-)

You all have been so encouraging, I really appreciate the reassurances. I suppose the real limiting factor would be airline ticket availability and synching that with room reservations, but I'll get to work (well, actually, fun).

We once had only airline tickets purchased months in advance and then we found out we were going to be grandparents for the first time during the week we were scheduled to fly to Italy. What a dilemma. We made no other plans leading up to the due date. We called the airline to see what our rebooking options would be for the following summer (our only months when we could vacation). We gave ourselves a 2 day chance to wait or cancel our flight close to the due date.

The night before we would have cancelled we got a 3 AM call. We drove 6 hours to see her, take pictures and hold her. Priceless. We booked a first hotel and week long rental in Venice then drove to LA, hopped on a plane and just winged it for the next 3 weeks. Very freeing! You can do it!

You have time - find several options for flights - different airlines, different connections, different days. I can't believe you wouldn't be able to find flight availability a couple weeks ahead of departure, especially for October (and late in the month is probably as good or better than early in the month).

The only thing you need to get started is a start and end date. Then, pick your airline and book it. Then, pick a hotel for first spot. After that, you can use hotel wifi to determine train, location, and all other sleeping spots as you go along your travels. For instance, after you arrive in Rome - you can decide where to go next and go online to book your next room. You have to be flexible though. This could be a lot of fun.

You can do this easily! One time we planned a trip a month out from US to Russia and we had to get a Visa too.

My wife and I have the same dilemma with 90+ aged parents and trying to decide whether to stay domestic or chance it abroad. We haven't booked it yet--waiting for good fares--but are planning on Rome for 9 days in February. Obviously we don't know what my parents' respective health will be seven months hence, but what we've decided to do is book the air, book the hotel or apartment, and take out trip insurance for that amount, probably in the vicinity of $2500 non-refundable, for which our insurance company would charge about a hundred bucks. Certainly a financial peace of mind. We've done it for our past two European trips because my parents haven't been well for a few years, and there's always a chance that we might have to cancel. Even though we haven't used it, I feel it was money well-spent.