No reservations

Only risks are...

1. You spend several hours each day looking for and trying to decide on a place to sleep that night

2. You end up with something that's more expensive, less nice, and more poorly located than you would have liked

Personally, I'm done with wasting my valuable time in Europe chasing a decent place to sleep (more often than not, ending up in a funky, badly-located, too-expensive place that bums me out) - been there, done that, won't do it again. I have enough spare time here at home to do the search for accommodations, and the internet has more than enough information easily available - IMHO, it's foolish to think you will do better while you're overseas.

Europe is crowded with tourists now. The best places get booked up almost a year in advance. With each passing day, the pickings get slimmer and slimmer. Although booking long in advance locks you in to a schedule, I've come to conclude that this actually increases your freedom - because you get back all that time which you would have invested searching for a bed, you can spend that time doing what you went to Europe for - enjoying the place.

I travel flexibly but have been gradually booking my hotels a bit farther out. I don't travel quite as shoulder-season as you are planning, and I have been running into a lot of location-vs-price trade-offs. I now mostly book at least 2 days ahead. I would never want to just show up; that model doesn't work as well as it used to, because everyone else (including the people who will arrive in town hours after you do) booked their rooms online as soon as they knew where they wanted to spend the night. What remains may well be OK (I haven't had disasters), but it will almost certainly be lower-value-per-dollar places.

The arrive-and-look technique will be riskier if you need something other than a double room, are staying more than a night or two and/or are on a tight budget. And of course if you run into some sort of festival, you're in big trouble. One advantage of hitting the internet at least a few days in advance is that you'll have an early warning of such special events, because you will see that there's almost nothing available in town, and the rates for the remaining places will seem to have doubled. This is not information you want to discover when you get off a train at 5 PM.

I use booking.com. One must be careful about cancellation policies, because they definitely vary from lodging to lodging, but it's pretty common to be able to cancel as long as you do so at least 3 days in advance (be sure you understand the definition of "3 days"). I've occasionally seen more generous cancellation rules.

As some others have pointed out here and a few other threads, booking ahead actually gives you more freedom to enjoy your vacation and do what you want to do instead of wasting valuable time finding places where you can stay. If you REALLY want to wait til the last minute, I would book at LEAST 2 days in advance like the previous poster said.....that way you aren’t scrambling the night before you are kicked out of your lodging finding some place for the next night.

Another thing that you can save on is train tickets, because if you book your long distance trips ahead of time, you can save almost half of the cost.

I did a trip like you are thinking once, I was skiing in the Italian Alps, and we had 10 days to kill before we needed to be back in Rome, so we showed up, bought train tickets to Paris that morning and started our trip to Paris, Dublin, and Liverpool. We were mainly on flights and a ferry, and we stayed with some friends in Paris and Liverpool, but we did spend a lot of our nights around a computer trying to figure out what was happening next and how to get there. It was a fun trip, but not the best use of our time.

I am travelling in April and May, and briefly considered making a change by a day or so but it wasn't possible because the place in Florence was already booked. So not booking gives you flexibility but instead you lose time looking, lose peace of mind that you are set for accommodation and end up getting whatever is available, which may not be what you want. Even when I looked in September, one place we wanted to stay in Tuscany was already full. After Easter in Italy is considered high season.

I'd make sure to have a place booked for the first night or two. You don't want to be jet-lagged and with no place to crash. Make sure you have a decent phone plan or access to wifi. Go to the usual websites once you've reached Italy and book a couple of days ahead, look for free cancellations. You should be fine. That way, you won't be going from hotel to hotel looking for a place, yet you'll be preserving that sense of adventure and spontaneity, and can change your plans. Go for it! And have a great trip.

The idea of traveling 'untethered' and totally flexible is a nice idea, provided you have little, to no expectations and have A LOT of time. As others have pointed out, you will be spending (wasting) a lot of time looking for accommodations, transportation and restaurants if you don't do some prior planning. The last 30-years the price of air travel has dropped and the frequency of flights have increased dramatically, this has allowed a greater volume of people, worldwide to travel to all the known destinations. Italy today really doesn't have an off-season anymore, the last 10-years have seen the rise of travelers from China and India, which has flooded an already active and thriving tourism market. If you're insistent on traveling without any set itinerary or, reservations of any kind, stick to small towns, and make sure to carry enough cash to pay as the small towns and hamlets are more apt to be old school.

We did a trip a bit like this about ten years ago. Venice, Verona, Como, Assisi, Firenze, Roma. We had Venice and Verona booked before we arrived, booked Como while in Venice, booked Assisi while in Verona and so on. Essentially keeping a jump ahead, so that we always had a hotel booked when we arrived.

More recent trips, we have always had the complete trip booked.

I hate to rain on the parade, but no I wouldn’t do it. The free as a bird days are over, and with technology, hotels know if they’ve got the last few rooms in town and will set prices accordingly. Spending a lot of Euros for a lousy inconvenient hotel is a bitter pill to swallow.

We did that one time and it was kind of the opposite of vacation. We spent so much time trying to find a room that we didn’t enjoy our time enough. I had done a lot of research in advance and outlined places that I would like to stay in each area we were wanting to visit, but when we would get to those towns those places were full. Literally one of the six locations had room where I had wanted to stay and it was only available for our first night there and then booked after that.

I usually find it works best to put together a rough outline of what you want to do, but book the rooms at the hotels where you want to stay in advance. For me, sleep is really important in a comfortable bed so I am just not willing to take whatever is available. We spend thousands of dollars to take these European vacations, so hotels are one element that I have learned to fix and then be flexible from there.

You're going in May -- take a look at the schedule of (many) holidays in May, when local people may be traveling as well as foreign tourists. So understand what everyone else has said -- spending hours looking for a place to stay is NO FUN.
BTW, if you have a car you have a little more flexibility since you can move on to the next town ... Or you can find a place to park and sleep in the car overnight (have done that -- and I don't recommend it!)

My husband and I had the unfortunate experience once of not having a reservation. Instead of enjoying a wonderful celebration meal, we were busy trying to locate an available hotel in numerous towns. We ended up eating at a fast food location because we had spent so much time trying to locate a hotel that wasn’t creepy during a busy weekend. This happened in the US, but it taught us to never waste vacation time with tedious planning tasks.

If you hit that lotto jack pot where now money is no object for you then go for it

I agree with the others, and would not want to try the "spontaneous approach" these days, especially in April and May. There's no way I want to spend part of my holiday on the computer or phone trying to find a place to sleep in the next town I'll be visiting. As others have said, that may result in a room that costs more than I budgeted, located in a dodgy part of town or far from the sights, or something that doesn't fit my desired "comfort level".

With the advent of internet booking, and given that Europe has become much busier in the last few years, rooms in many places seem to book up quickly and well in advance. If you want to use the spontaneous approach, I won't say that you won't be able to find any rooms, but you may find it's more work and trouble than you thought.

These days I always have all my rooms researched and booked well in advance of my trip.

Another idea is that you book your lodging ahead of time, but for longer periods of time and you just going with the flow for your daily activity.....for example, if you lock down lodging in the middle of Tuscany in an agriturismo, you can have your car and go wherever the wind blows you each day.....still a bit of freedom, but you are safe with a place to stay,

Another idea is that you book your lodging ahead of time, but for
longer periods of time and you just going with the flow for your daily
activity.....for example, if you lock down lodging in the middle of
Tuscany in an agriturismo, you can have your car and go wherever the
wind blows you each day.....still a bit of freedom, but you are safe
with a place to stay,

Agree with Katherine, having a base locked in with flexible daytrips is key. Especially in April, which is shoulder season but quickly becoming a popular time to travel to Italy, into May which the last 5 years or so has turned into full-fledged high season.

That time of year is not so busy that all the attractions or little towns to visit are sold out, but lodging, whether it be hotel, B&B or apartment, is finite and at any place good enough to stay and a good enough value, will sell out rather quickly.

One more advantage to the flexible daytrips way is you can plan around weather. Outside activities, no matter how wonderful, in the rain or cold are not so wonderful anymore.

Enjoy your planning!

Singing with the choir here, Lynn: running around trying to find an accommodation during high-ish season isn't how I'd want to spend my time. Additionally, if you're trying to locate accommodations on a device, you'd want to be especially careful of location if driving a car: there may be towns/cities you're visiting where you won't be able to take the car into the centers or to random neighborhoods at all, or not without prior arrangement just to unload and then move it elsewhere. Parking may not be a given at every accommodation either.

Maybe you already knew that but you haven't mentioned if you'd been to Italy before or how much reading you've done regarding the ins-and-outs of driving so apologies if it's old news. :O)

Anyway, research in advance will allow you to nail down hotels/B&Bs which are convenient for road-trippers. As Katherine & Jay mentioned, freedom of movement/itinerary can be just as possible from base locations...which brings up this caution: Theft from unattended rental vehicles is just common enough that I personally wouldn't leave anything in a car while sightseeing. There's some peace of mind to be had with the bags/valuables safely stowed at the hotel whilst tooling around having fun.

I think in this day and age, Acraven's approach to spontaneity is probably the most practical.

The last time I traveled to Europe with no reservations was in 2000, essentially before the curve went to booking sites. In that era, traveling without reservations was soooo freeing. It felt like I had totally left 'the system' and the 'set in my secure ways' behind. I'm sad for anyone who never got to travel that way. Only once, did I have to walk next door to another hotel because one was full...actually it was across the plaza. I never hunted for rooms and I got hotels where I wanted them. Then again, I didn't/don't travel in the summer. That being said, one has to be willing to let go to travel spontaneously, even Acraven's way, and often, if not traveling alone the other party is not as comfortable with this system. So check your travel partner(s) as well.

However, travel is an adventure, and this can be part of it. Travel is so much more than just seeing St Peter's, etc.