Extended stay in Italy

I frequently don't make reservations more than a few days before arrival. There's a financial risk to that if you are heading to high-demand places like Venice. It's not unusual for me to end up in a hotel that's farther from the center of town than I'd like, because the a better location was a lot more expensive.

The fact that you plan to drive means you can be more flexible about where you stay. You don't have to be in a town with good public transportation links.

I don't think anyone really knows what's going to happen with hotel rates over the remainder of the year. How will supply and demand align?

I would definitely not wait until I arrived in the new area and start looking then. Almost everyone books rooms at least the night before, so you'd be dealing with the leftovers.

What time of year are you planning? Summer findings (although maybe not this year) will be harder to come by than shoulder season.
I’d love to see your itinerary when you have some ideas. Do you speak Italian? I’ve thought about retiring there also.

As a seasoned traveler you may already be aware that there are potentially steep penalties for over staying. 90 days includes both arrival and departure days. I would suggest leaving yourself some wiggle room perhaps 85 days.

Would a hybrid approach work for you? Have blocks of time and rooms booked for places you know you want to stay. Leaving gaps in between to explore and wander. So say you started with 10 days booked in Tuscany and your next planned stop is the Dolomites for 5 days. Leave yourself a week or enough days of flexibility to get there.

If you're traveling in the high season, or to a very popular place like Venice, or looking to be somewhere during a big festival, you might want to nail down some reservations well ahead. Otherwise I'd suggest planning and reserving a few days ahead as you move along. That has worked for us in shoulder season in France. I use a tablet and wifi.

Just showing up in a city or town and then looking for a room seems time-consuming and risky. You probably don't want to be that spontaneous anyway. It helps if you're not too fussy about location or charm or amenities. And you'll need to consider parking, either at your hotel or nearby, preferably off-street.

I'd echo the advice about 90 days -- plan for a little less so you don't get caught in the Schengen trap.

In Nov 2003 and Mar 2005, I showed up in Venice without a hotel reservation and found a room near the train station.

That was gutsy, but not everyone was traveling with smartphones back then, so you weren't (virtually) the only traveler arriving in Venice that day without a room reservation.

In addition, March and November are pretty far off-season in Venice, I think. I'm not sure what time our original poster plans to take this tip.

I agree acraven and wouldn't recommend doing that today if traveling during the high season.

That is exactly how we did it 30 years ago. Now we were not driving but would hit the TI in the train station on arrival. Never spent more than 30 mins or so finding accommodations. To a degree we still do it that way today. But instead of the TI, it is hotel.com and other booking sites. We will still use the TI if convenient. We rarely make advance reservations other than the first and last nights or sometimes other when it is critical for timing or location. BUT -- for us. All we are interested in is a clean bed. We don't need a balcony overlooking the city. Just a decent bed in a decent location and good breakfast is a plus.

And as suggested up thread, only plan on 85 days. You do need a small pad of time just in case something happens.

Bring a mobile device to make searches online and simply search accommodations and make reservations the day before or a few days ahead as you travel. There will always be availability somewhere in town or nearby. I guarantee you.

In our wanderings, we had few reservations, only those nights that were fixed, and always found it easy to get rooms. Yes, a popular city in high season may require reservations well ahead, but knowledge is power, so having a short list of well vetted options for each city of interest is key. Then, since you usually know what you will be doing the next day, a call, or now through an app, you get a room for the next night or several nights. With a car, you will have more flexibility, since small places on the outskirts of a town, or the next town over, are good options, and usually offer better parking. Booking.com and Hotels.com have a wide variety of options, even in smaller towns.

Do not be swayed by the argument "You are going to spend all your time finding a hotel"; you won't, especially if prepared. Often I could walk into a town and find a place to stay quicker than most can locate the hotel they reserved six months ago.

Maybe goes unmentioned, but do understand the toll roads, speed cameras, and the dreaded ZTLs that seem to exist in even small towns now. Hate to be giving advice a year from now on what to do with all the fine notices.

There are areas where demand simply outstrips supply (coastal Cornwall and Isle of Skye for example), and late attempts to find public-transit-accessible lodging in such places can result in no availability or only very crummy or very expensive options. To me, a $200+/night room is the same as no room.

Towns that are generally rather well-supplied with lodgings can be very difficult during periods of special events, and those can have ripple effects in other towns in the same area. For this reason, I highly recommend checking availability several days ahead of time so you'll have an early warning if things look grim. If it appears many rooms are available, you may feel safe waiting another day or two to book.

I remember posts from a couple of folks on this forum who were facing shockingly high room costs (I think over $500/night) because they really, really needed to stay in a specific city (probably flying out the next morning) and there was in one case a major rock concert scheduled (that was Dublin) and in another case a major soccer/football play-off game (that was in Madrid). I try to carry a list of major holidays and festivals with me, but my pre-trip research has never warned me about rock concerts or play-off games. Or the major bicycle race I bumped into.

I agree with acraven... as well as others above ... search Air BnB as well- alot have refundable cancellations ... If you already know alot of towns you want to visit you can be flexible with check-ins and only book hotels/BnB’s which have penalty free cancellations.
As far as your rental car- LOOK OUT for those ZTL’S!!!! You certainly do not want to get thousands of dollars of fines years later which can Definitely happen according to many posters on this and other travel forums!

With that being said, enjoy! Italy is amazing and my favorite❣️✨