Italy - to reserve ahead or not to

If I travel the month of May all over Italy do I need to reserve everything or can I go and wing it and still be able to find places to stay,

Maybe if I was going the first week of December but I would not try it as a novice traveler to Italy in May;

but I'll mention two possible ways you can do this:

only if you are a backpacker on a budget staying in hostels;

or, you don't care how much you pay to stay somewhere (but then you would not need to ask a travel forum)

either way can be stressful and effect the quality of your trip and those around you when you have not found some place stay or spend time searching instead of chilling traveling taking in the sites;

Also, fast trains are expensive. Tickets go on sale months in advance at large discounts. The discounted tickets are limited, so buying in advance can save you a lot . . . or conversely, buying last minute can be unnecessarily expensive. Regional trains (much slower) are not discounted, so if you have lots time, then that doesn't matter.

There are some sights that usually need to be reserved well in advance - either tickets are limited or ticket lines are usually long (not 15 minutes, could be an hour, could be even more).

I hear ya, it can be stressful at times.

I am not a back packer and can afford more expensive places (not sure why I would not be on this forum), not that I want to spend a lot on hotels.

I have traveled all of Canada and the US as well as Germany and Poland and some small countries doing it this way and the odd time have been caught when its a Holiday weekend.

I just wasn't sure when it came to Italy in May if it could be pulled off and that I would be able to find accommodation a few days ahead of each destination.

With the proviso that all bets are off if you end up hitting a special event somewhere, it can probably be done if you're not looking for special accommodations and have the financial resources to pay a bit more than expected because the early birds have snapped up all the best deals. In 2015 (Italy, Germany, the Balkans) I was booking places 24 to 48 hours ahead of time without too much difficulty except one place on the Istrian coast. It became a bit more difficult in Spain in 2016, and I began trying to finalize hotel reservations at least 48 hours ahead. I pushed it out a bit more last year in France and England (and still had issues in Cornwall), because I found I was having to make unpleasant trade-offs between price and location.

It may matter that I wasn't attempting to make late bookings for Rome, Florence or Venice. I'd be afraid of pushing my luck in Venice, where costs run very high by Italian standards.

Keep in mind that the longer you want to stay, the harder it's likely to be to pick up a last-minute room with a good balance of price to value. People cancel all the time, but the odds are not good that there will be a late cancellation that aligns with the four or five nights you want.

Coliseums to see...

May is already High Season in much of Italy. Regarding the most popular attractions in the most popular Italian cities, you will want to pre-purchase tickets or make advance reservations (where applicable), or make use of tourist passes to avoid standing in very long, often shadeless ticket lines. I don't know what is on your must-see list or where in Italy you intend to go but otherwise trying to spontaneously sightsee the tourist magnets would likely be an exercise in frustration. It's not impossible at certain of them but some homework is necessary?

Fascinating topic, especially for the anal-retentive planners like myself!

acraven's words really ring true for me, and yes, it all comes down to 'unpleasant trade-offs'. This was discussed in another thread of mine, and it basically is this: Because of last-minute booking, if you have to experience one or two nights in a non-preferred, logistically-awkward hotel, would you ruminate/fixate on it so much that it ruins the rest of your trip, or alternatively would you chalk it up to experience, reveling in the other days of May where you were footloose & fancy-free, booking spontaneously and grooving on it?

That's a dilemma for me, a question I cannot answer at this point & something I probably need travel therapy for!

I love to plan these European journeys, and I think I've become pret-ty good at 'planning-with-spontaneity-built-in'--I don't routinely pre-book attractions or restaurants. As I stated in the other thread, the main part of spontaneity I'd miss with advance planning is when I'm having such a good time in one place and don't want to leave but have to because of train tickets to another destination & booked hotel reservations there.

Always plan your itinerary and reserve as much as possible. Research what to see, where to stay and even make a list of restaurants that are close to where you are staying. TripAdvisor is great for that.

Renting a car in Italy is an option, but better to stick with trains for one person. Parking can be a real problem in many Italian cities. Also, the Autostrada has very high tolls.

Perhaps you could get a feel for what May will be like by doing a little checking now. Find potential areas you want to visit and look for accommodations there. Many hotels and agriturismos have calendars for booking a room. You could get a feel for how much has been booked already and guess the likelihood of finding something last minute.

I'm thinking what you gain in flexibility and spontaneity will be at least partially offset with spending a significant amount of time every day with the logistics of finding transportation and lodging.

There is something very appealing about throwing caution to the wind and getting off the plane at FCO with no advanced plan, taking a magical mystery tour. Unfortunately, my OCD doesn't allow me to entertain this thought seriously.

When we went to Tuscany in December 2015, we were locked in to a few days because of advanced reservations for Walks of Italy tours and a food an wine tasting at our agriturismo. The rest of the time was free form, we could choose from a list compiled before we left and some things suggested to us by our hosts. We went to bed more than a few times with no idea where we would go the next day, but we did know where we would end up at the end of the day. The basics - transportation and accommodation were covered and we worked within that framework.

There is something very appealing about throwing caution to the wind
and getting off the plane at FCO with no advanced plan, taking a
magical mystery tour. Unfortunately, my OCD doesn't allow me to
entertain this thought seriously.

Does OCD and anal-retentiveness work hand-in-hand? Discuss amongst yourselves...

All's I can say is that by advance planning the main structure of things, working my way from the outside in--air, then ground transportation, then lodging--I've had a minimum of those 'oh sh-t, what do we do now?' moments.

Worst--not even that bad--was when we were traveling by train from Lucerne to Milan--a spectacular ride through a snowstorm in the Alps BTW--we were informed that the train was making an unscheduled stop at Chiasso on the Swiss/Italo border, we'd have to change trains and would get to Milano late, where we had advance tix to continue on to Florence. I don't know what had made me build extra time in advance into the stop in Milan, but I did, and we made the Florence train.

My point is that the unexpected happens quite often in Italy even when you've planned much of it out.

Does OCD and anal-retentiveness work hand-in-hand? Discuss amongst yourselves...

Absolutely!

Also, my wife and I (mostly "I") enjoy the planning stages. We get RS books, watch RS episodes on YouTube and even buy travel videos to get ideas. We then triage (she's a nurse) our wishes, design an itinerary, then throw out half of what we planned since we (uh, I) tend to plan activities that would comfortably fit in a 28 hour day if you don't expect to sleep.

At a minimum, I think that everyone should plan for one in every three days be a "down" day, were nothing is booked. That allows for at least a little spontaneity.

I spent a couple weeks in Italy (in October) traveling solo as a part of a longer trip, and had a bucket list of places I thought I might want to go see. Except for Venice, which I booked months in advance, I booked hotels about 48 hours ahead of arrival, and that worked fine. I found that booking.com was a valuable resource. I didn't purchase train tickets in advance, although I did advance research on the train schedules to make sure I knew my travel options, and I didn't do any advance booking of sights or restaurants. It was pretty fun, although I don't think I'd do it this way if I had a traveling companion. I have no experience with spur of the moment car rentals except to note that car rental agencies have shorter hours of operation in Italy, and except at airports, they are often closed on Saturday afternoons and Sundays.

The last time I did not book ahead every night was on our Portugal trip in 2008. It's so easy to do that everyone does it and you risk ending up with substandard (quality, location) accommodations at $250 night. I would expect May to be quite busy in Italy. You might also want to consider whether you want to spend a chunk of your days during your trip hunting for a place to stay. You can still spontaneous in planning your day, or potentially with day trips.

You can do it. Too much emphasis is placed on advance planning. There are some who like to have every hour planned and your odd if you don't. We generally lock down the first night or so and the last night or so. You have to be flexible. TIs are still great sources for lodging. Haven't slept in the train station in a couple of decades. Watch the weekends. We try not to move over the weekend.

There are many here who would not dream of doing this and will give you all kinds of cautions. But if you done it before you have some idea of how to be flexible. Our son and dil did an five month around the world honeymoon without a single advance (more than two days) reservation. Provides a great sense of adventure.

Go for it. Then come back and tell the doubters how easy it was.

But if you done it before you have some idea of how to be flexible.

Frank has a good point: there's a difference between someone already used to and comfortable operating on the fly if and someone who is not. Ventures, if you've already managed well by finding/booking your accommodations with your smart phone, then go for it. Spontaneous train travel wouldn't be an issue either except for cost.

We don't pre-book restaurants, and would hate to have our days planned to the minute. My main concern was with some major attractions that have very (!) long ticket lines or which mandate pre-reservations that can fill pretty far ahead of time. That's where a little advance footwork/prep might be useful if they're on your list.