September or October for a 3 week trip to Italy?

Both are still high season in most areas so you'll still encounter crowds. You may have better weather in September but I would try for the end of October or November if possible. Also, it really depends on where you want to go. If you plan on visiting the beaches or the CT then I would go in September.

Donna

I've been to Italy in both Sept and Oct and to tell you the truth, didn't notice any appreciable difference between the two for cost/crowds/weather. All of those things depend more on where you go, than when (at least between Sept & Oct). I would say if cost is concern, then go when you can get cheapest airfare. I don't think hotel prices drop much until after Oct. As the previous poster noted if you plan on CT then Sept might be a bit warmer.

I'd choose October, not as hot, not quite as many tourists. If weather is a big consideration, go to wunderground.com and look for the trip planner and find the historical weather for the last 10 years or so, day by day. That will give you some idea of what you are in for in different regions.

Even in October, if you don't deal well with heat, I suggest you book lodgings with A/C, especially from Florence southward.

Our preference is mid Sept to the end of October. Remembers the days are getting shorter especially as you go towards the end of October so you have less time outdoors. Weather is generally milder, dryer, and less variable but it can still be hot in September. Don't notice much difference in crowds or prices BUT haven't been in Italy in July or August so maybe the crowds are much worse at that time - I don't know.

I will give my opinion that the OP is intending to go in September or October, and should not be talked into going in "late October or early November", when that is not their plan in the first place.

Mid-September to maybe the 3rd week in October would be fine.
But there could be a big difference, weatherwise, between mid-September to 3rd week in October, compared to "later October to early November."

From what I've seen, on average, late October or early November are times of the year where it's more likely that you could have a spate of bad weather that can, if lasting over several days, can really put a damper on your expensive vacation.

I realize there will be people here who have gone at that time and will report the weather was wonderful. Good for them, but that's just anecdotal evidence and an inexperienced traveler to that area wants to take anecdotal evidence, with all due respect, with the proverbial grain of salt.

I'm just talking about averages and the fact that it's a kind of high stakes decision in terms of your enjoyment of your vacation. One day of bad weather is one thing, but several days or prolonged unpleasant weather can ruin your experience.
This is advice for someone who has a choice of what dates to go.

Looks like we are leaning toward September seeing we want to visit the beaches on AC. Now all we have to figure out is a doable itinerary. 😄

We reworked out our itinerary a little bit more at a slow base.

Arrive Milan early (Last Supper) travel to Varenna.
4 nights Varenna (day trip Bermina Express to Swizerland)
3 nights Castelrotto (not sure about this leg of journey is worth it with the long trip getting there)
2 nights Venice
3 nights Florence (day trips - Siena, Pisa, Assisi)
2 nights Cinque Terre
2 nights Sorrento (day trips - Pompeii, Isle of Capri, Amalfi Coast)
4 nights Rome

Any input greatly appreciated.
Diane

2 nights is not nearly long enough for the Amalfi coast. But if your interests there run to beaches you will be disappointed anyway. What little beach there is tends to be pebbly. However, seeing the ruins of Pompeii, the isle of Capri, and hopping from town to town along the coast will take 3 days minimum.

Assisi doesn't really make a good day trip from Florence. It's too far, and there is far to much to see there in just a day. Better to stay 2 nights.

The only comment I have is: why are you going to Florence? With 3 nights there you'll have 2 full days and if you day trip to other places both days, when will you see Florence?

EDIT Okay, I have another comment. If you're only going to places to say you've been there then your itinerary is fine.

October might be a bit risky for the CT. I would add 1 day in the Amalfi coast and visit Ercolano and Paestum as well as Ischia and allthe islands near Sorento.
Add one more day to Florence and day trip to Siena or Grosetto.

October might be a bit risky for the CT. I would add 1 day in the Amalfi coast and visit Ercolano and Paestum as well as Ischia and allthe islands near Sorento.
Add one more day to Florence and day trip to Siena or Grosetto or Lucca.

So I can adjust my time to take away CT and add more time for Amalfi Coast Towns. But, any suggestions about Dolomites. Should I take it off my itinerary and add more time at Florence and Sorrento?

As was already mentioned above, if you spend 3 nights in Florence and do the 3 day trips you list, you won't have any time to see Florence.

Where you go and how much time you spend there depends much more on your interests than on any template itinerary.

Take into account how much time you will use going from location to location. For instance, it will take most of a day to get from the CT to Sorrento and half a day to get from there to Rome. Even going from Venice to Florence will use up close to a half-day . . . You have to pack, check out, get from the hotel to the train station with your luggage, then get to your next hotel, check in and unpack. You have to leave enough leeway so you don't miss a train because of slow traffic or because you are stuck in line to buy tickets, or just because you find the train station confusing and don't know where your train is.

Too many 2- and 3-night stays in succession can be tiring and 2-night stays only really give you one full day to sightsee and enjoy. I guess there are places in Italy that aren't enjoyable or worthwhile, but I haven't found them yet. Wherever you go, you are going to have a good time, so my advice is to slow down, soak it up and enjoy it. Less is truly more when you travel.

Thanks for all the responses. So, what I am hearing is that I have to slow down. We're thinking of taking away the 3 days of Castelrotto (Dolomites) that will give us more time around Florence, Sorrento, Rome. Can someone give me some feedback on how to handle 14 days in that area of Italy. We are trying to do bus/train travel. You guys are a wealth of information. Thanks for all of your help!
Diane

I would ditch Castelrotto and spend more time in other areas, not because it's not worth seeing but because it's so out of the way. Whatever you decide, take heed of Chani's advice. With a lot of 1-or 2-night stays, any disruption (delayed transportation, for example) will cause the dominoes to start falling.

Skip Assisi and I suggest to take a full day trip (tour) to the hill towns of Chianti, Siena, Pisa and one town which I don't remember, lunch is included (also wine) in an agro tourism farm as well as sightseeing. I paid $120.00 five years ago and lasted twelve hours. Just go to a travel office as soon as you arrive in Florence and you'll save time. Don't miss the two main museums there and go before 9:00 am to secure tickets. Also, see if you pass Switzerland this time and concentrate on Italy. Arriving in Milan you could go to Lake Cuomo for a day trip too.
Buon viaggio!

So your itinerary is:
4 nights Varenna (day trip Bermina Express to Swizerland)
3 nights Castelrotto (deleted)
2 nights Venice
3 nights Florence (day trips - Siena, Pisa, Assisi)
2 nights Cinque Terre
2 nights Sorrento (day trips - Pompeii, Isle of Capri, Amalfi Coast)
4 nights Rome*

I would add the 3 "deleted" nights to Sorrento. I'd also skip the CT and add a day each to Venice and Florence or Rome. I agree that Assisi should be omitted - too far. It takes so long to get to Sorrento and to the CT, that I'd only go to one and Sorrento has so much more to offer.

It's always a tough call to listen to peoples' advice on what to skip b/c it's such a subjective decision and what you're interested in. We loved the CT and will go back there -- if it looks appealing to you, go for it! My only suggestion is that rather than use your time out of Florence for a day trip to Pisa, just hit it on your way from CT to Florence during a train layover. We just went to the Tower and had lunch in about four hours and the station offers bag storage.

Thanks for all the input. We revamped once again our plans.
Arrive Naples
Stay in Sorrento (3-4days)
Go to Rome (3-4 days)
Go to CT (3-4 days) we think it's worth the trip up there
Go to Florence (3-4 days)
Go to Venice (2 days)
Go to Varenna (4 days)
Go to Milan (1 day)
Fly home

It is a work in progress, we're pretty much set on these places, it's just the sequence of our travel. But, I think this makes the most sense. All train travel. We can add a couple of days if we feel we need to.

Thanks for your help!
Diane

Diane...You've got it perfect!!!

Thanks Gerri! Next up airfare and hotels.

Diane

It depends on where you're going, what your plans are and what type weather you like. I like hot weather. We were there in Aug. 2013 and it was one of the hottest summers on record. It was over 100 F. in Rome and Florence. But cooler farther south in Sorrento and the Amalfi coast. When swimming inn Sorrento, the water was chilly. This was mid August. I, personally would be cold in Sept. and definately in Oct. As far north as Milan or the lake district, Oct. would be cold in Oct.So, you see, too many variables to know what to tell you.
Enjoy though, whenever you go. I LOVE ITALY!!!

It depends on where you're going, what your plans are and what type weather you like. I like hot weather. We were there in Aug. 2013 and it was one of the hottest summers on record. It was over 100 F. in Rome and Florence. But cooler farther south in Sorrento and the Amalfi coast. When swimming inn Sorrento, the water was chilly. This was mid August. I, personally would be cold in Sept. and definately in Oct. As far north as Milan or the lake district, Oct. would be cold in Oct.So, you see, too many variables to know what to tell you.
Enjoy though, whenever you go. I LOVE ITALY!!!

Diane:

Your revised itinerary looks great. But unless you REALLY want to relax and do nothing, 4 days in Varenna is a lot. I'd take a day from there and add it to Venice. Just a slight tweak - the rest is wonderful and I wouldn't change a thing!

I think your right Harold. We were looking at that as well. Not too sure about adding it to Venice though.
Diane

I would definitely add a night to Venice. If you start to explore, it can be full of delightful surprises. I would also add 1 night to Sorrento and take it away from the CT, because you're starting there and there's that ugly jetlag at the beginning of a trip.

Good point Chani!