"""the good news is that at this time of year there will be less tourists and pretty good weather (usually)"""

We were in Italy in late Sept a few years ago. When we arrived by plane into Florence, it was pouring down rain. Our flight was diverted to Zurich then Florence, and arrived about 3-4 hours late. We then spent 5 nights in Lucca, 2 weeks in the Val d'Orica, then Venice.

We ended the trip with 5 nights in Florence in early Oct - because I figured that the crowds would be fewer then. The proprietor of our B&B told us that October is one of the most crowded times of the year, because many guests assumed (like we did) that it would be less crowded then. We visited Florence after a week in Venice, and we were overwhelmed with the congestion, noise, skinny sidewalks, and automobiles. We enjoyed Florence (this was about our 4th trip there), but after Venice it was quite a shock.

Stu Dudley

There�s an old saying Stu

The plural of anecdotes is not data!

Adding a 'not' to Raymond Wolfinger�s famous quote doesn't make sense. The point of the quote is that data comes from something, in this case a collection of anecdotes.

Personal interests are, of course, important, and there are some interesting festivals that might be fun if you just happened to be there. Many, however, are really not unique and are as much about noise, crowds, spilled beer and bad music as they are about something special, and may not be worth the time and money to get to them, especially if one is using time and skipping world class sights that can be seen only in one place. After you have seen Rome, Pompeii and Venice, perhaps throw in other stuff.
IMHO, a lot of Renaissance Festivals are really, “seen one, seen them all,” but there are celebrations and carnivals that are so unique as to be travel destinations. I have not been, but people make special trips to Venice for Carnival and to Siena for the Palio.
I made a winter trip to Basel for Fasnacht and other winter Fire festivals in Switzerland. That was the entire purpose of the trip and I hope do it again. It is an amazing experience that we planned for specifically.
How much is every day of your trip costing you? Time? Money? What is the reward? On long trips, a break is needed, but not on such a short one.
Annecdotes may not be stats, but can be useful, especially from people like Stu (and my go to for advice, St Cirq), who have given me tips on unique places and cities that others discounted and best times of day and even times of year to see things. Their personal experience gave me guidance that made some of my best travel memories.
From my own accecdotes, I must take rain with me to Italy in Spring because I have been in torrential downpours in Rome twice, in Venice with unexpected rain and more flooding than usual, three days of nothing but rain in Lucca, storms where everyone but me was sick on the ferry to Capri, etc. We always have backup plans.
I don’t listen only to a dissenting voice, but do take note of it.

About the crowds in October... Global tourism has increased tourist numbers in every month of the year and the numbers keep going up. Some places we loved visiting 20 years ago are border-line unpleasant now. We were told by the owner of the Rome hotel where we've stayed several times that October became the most-booked month of the year after 9/11. She speculated that people who had their plans cancelled around 9/11 re-booked a month or so later and found it was a great time to visit.

Predicting rain risk is impossible... especially when all weather becomes more unpredictable every year.

October has less North American tourists with their families. It has less European families on longer trips. But all the Europeans that had to work in August are traveling. Plus those that didn't want to deal with the heat. You can also add all the school trips. In addition I think there are some school holidays across Europe in October. Tourists numbers don't drop off until November. Check hotel prices. You'll often see a drop in prices that happens in November until mid December.

October is the rainy season. Doesn't mean it might not be beach weather one day but you could see Noah and his ark the next.

It wasn't supposed to make sense it make humour.

Informative information about 15 days in France / Italy
What about Coronavirus cases in Italy.

Paris, Venice and Rome but pace yourself�.Venice is glorious and Paris is my favorite�.Our Rome Trip was our second,,,too crowded and graffiti even in the Vatican, sad.

We are currently in Umbria for one month, staying in one location, our concession to Covid but also a desire this time to feel more like a local. Having said that, I think it needs to be emphasized that travel is not one size fits all. The OP’s original plan is not only do-able, but it would work well for many.

We “showed” my sister-in-law Europe with an obviously ambitious, definitely NOT for everyone, 16 countries in 30 days. Our blog is still out there (linked to our trip report) to show what a success it turned out to be. For US. Yes, stuff happens. In our case, there was a migrant crisis, borders were closed, and we simply deleted a couple of countries and added a couple more on the way. Flights in Europe were/are cheap and available to allow such last second changes.

A couple years ago, our daughter wanted to fly with us from Copenhagen, where we were briefly visiting friends, for a few days in the Dolomites. Although our flight was to Venice, her time was very limited and she didn’t want to waste time there. We insisted she at least “see” Venice. We flew into Venice late afternoon, saw some of it, had a great dinner in a locals area; got up in the morning and did a three-hour walking tour before the throngs arrived. Of course, a few days would be better. However, that is not always available to everyone. A memorable visit that will forever allow her to at least have a good sense of the place.

Although we drove down to Vernazza on a quiet November day years ago, we saw the rest of CT in one day a few years ago. We were staying in Rapallo, took the train, hiked between the three available towns, took the train to the others. Although great weather helped, and that is always a consideration in short visits, we had a wonderful full day.

You do need to be mindful of travel delays, weather, and other things that can get in your way, but don’t focus on all the what-ifs. We have had many “packed” trips over the years, and, for us, it has always worked. We travel light, get up early and stay out late. That’s a combination that has served us well, and we are decades older than the OP.

surely is it "fewer" tourists, they are not sand ;-)

FTR - Bologna does have a left luggage facility at the train station ground level. I've used it in the past, but not sure if covid has changed things.

I find it odd people are complaining about how crowded Florence is, but not Venice.I find Venice much more crowded.


**October 9 - train to Milan then rent a car and drive to Alba(arrive at 1pm) for the truffle festival and stay the night.**

Have you actually crunched the numbers on this? What's involved in checking out of your Airbnb, getting to the train station, time to Milan, time locating/picking up car rental, driving out of Milan, driving to Alba, finding parking, etc.? Have you looked at car rentals/prices? In the past, it's been cheaper to get a 3 day rental than a 2 day. Perhaps start planning your next trip to Italy and put Alba and that festival at the beginning or end (fly in or out of Milan).

"I find it odd people are complaining about how crowded Florence is, but not Venice. I find Venice much more crowded."

kybourbon, those are people who love Venice but not Florence. I'm team Florence, so I agree with your crowd estimates.

<<I find it odd people are complaining about how crowded Florence is, but not Venice.I find Venice much more crowded. >>

I don't find it odd at all. If you like a place and visit often you are much more likely to know how to avoid the crowds. And having done so you like it more - a virtuous circle.

Last time we visited Tuscany, we rented a villa with an Infiniti pool over looking Le Crete Sensi near Buonconvento just a ridiculous view over 20 miles of countryside. We drove into Florence for the day, couldn’t get parked, got caught by the ZTL cameras, overpaid for an awful lunch, visted the Uffizi with its (mainly) awful art, in the midst of being kicked and pushed around by cruise ship groups trying to keep up with their team leader who wad holding an umbrella.

Got back to our villa , the sun was setting, cracked open a bottle of Brunello and thought what a waste of a day. Chilled by the pool and then took our Springer hunting for truffles in the woods the day afterwards …,much more fun. Didn’t find any but the old girl was a badly trained nutter.

**I don't find it odd at all. If you like a place and visit often you are much more likely to know how to avoid the crowds. And having done so you like it more - a virtuous circle.**

Ditto for Florence.

** We drove into Florence for the day, couldn’t get parked, got caught by the ZTL cameras, overpaid for an awful lunch, visted the Uffizi with its (mainly) awful art, in the midst of being kicked and pushed around by cruise ship groups trying to keep up with their team leader who wad holding an umbrella.**

It's not Florence's fault that you broke the traffic laws and got caught. You could have had the same issue if you were staying outside of Venice and made a day trip in. It doesn't make sense to drive to Florence from Buonconvento which has a perfectly good train station. As for cruise ship crowds, Florence doesn't hold a candle to the numbers Venice has let in. They are both crowded cities full of high end shopping, but I've only seen Venice compared to Disney World, not Florence. YMMV

** I'm team Florence, so I agree with your crowd estimates.**

I'm actually team Siena and Rome over Florence/Venice.

Of course, the OP should go to the cities they feel the nust see, but they should be given the facts about crowds. As first time visitors to these cities, they probably want to see the main sites, not skirt them, especially with so little time for each city.

"Florence from Buonconvento which has a perfectly good train station"

sorry, don't use trains, thank you.

grdwaste, i think your plan is totally doable for a couple in their late 20's.
you need to remember that most people replying are over the age of 50 and travel differently. they have done all the mad rushing around.
I would keep your itinerary and just cut out CT part.

""most people replying are over the age of 50 and travel differently. they have done all the mad rushing around.""

And the next time we went to Europe, we visited the same places we visited on our "mad dash" trip. But on this second trip, we stayed longer at each location and actually visited the sites & cities we only "glanced at" on the first trip.

Stu Dudley

People who try to cram lots of sites into their itinerary are not divided by age so much as FOMO. That can kick in young or not until much later. "Will I regret not going to...."

If It's Tuesday, This Must Be Belgium.