Should we book our hotel or just show up?

If you're already sure of your itinerary, I can't think of a real benefit to showing up without your lodging figured out in advance. Booking my lodging in advance allows me to compare price and quality and research reviews of possible lodging. I would not enjoy arriving in a city with my luggage and then have to look around for what's available lodging-wise.

I used to be very flexible in my hotels, but we are now in the Internet Age.

People can find all sorts of places, well in advance, and snaffle them up.

These days, turning up and looking for what is left is exactly that - people will have searched and booked based on reviews and personal preferences, sometimes at pretty decent prices.

When you rock up you get what nobody else wanted. Sometimes you can get a really fabulous property at a rock bottom price. Sometimes.

But not often.

It's personal preference, your tolerance for planning or winging it really. Personally I prefer to spend time planning my trip so that my actual time on vacation is spent doing enjoyable things. Looking around for hotel rooms is not on the list of enjoyable things to do while on vacation. And some places (think Milan) really can book up at certain times of the year.

You can also get pretty good discounts at times for pre-booking. But always read the fine print VERY carefully. Some advance reservation discounts are no-cancellation policies and they are strictly enforced.

Unfortunately I agree with Nigel. The days of getting off the train, hitting the TI for a couple of recommendation, and checking-in is about over. Too many anal travelers that have to have everything last detailed nailed down. With the internet it is too easy for them to do that so as Nigel says a lot of the stuff is booked ahead especially in the bigger cities and popular areas. We use to travel with only the first and last night pinned down. Still do a little bit but not as frequently. When we do it is mostly in the off the beaten path (that really doesn't exist anymore, either) in off season. With a tight schedule you are proposing, I would join the mob and book ahead.

I agree with both of the first two comments. Besides who wants to get to town and spend their precious time looking for a hotel. There is so much to see and do, searching out a hotel is not fun! The hotel we stayed at in Cinque Terra was up 65 flights of stairs. In Rome, the hotel was on a 3rd floor. and if we had not had maps or directions to all of the hotels in Italy we'd of spent a lot of time searching. We did have an elevator (lift) in the hotel in Rome. Book ahead. Have a great trip!

agree with the other posters. Twas a time when the way to find places to stay ahead of time was to use guidebooks or the TI brochure a friend who already visited was kind enough to bring back. Plenty of space was booked on the fly. But the internet has made info available easily and instantly. And its easy to demo for yourself. Pick up your RS (or favorite) guidebook. Find the name of one of their carefully selected hotels. Now type it into Google. You instantly see hundreds of references to it. You don't need the guidebook to find it, anyone can. Now open Google Maps. Type the hotel name. When the map opens, click the "search nearby: hotels" blue link. Not only is your hotel on the map, so is everything else in town.

How many free beds do you think popular towns will have when you show up the day you want to stay? My guess is the occasional last-minute cancellation.

I'll add my $.02 worth. In addition to the obvious advantage earlier bookers will have in obtaining the best locations at the best prices, the real disadvantage to you is the time you will spend phoning around, walking around, etc. looking for rooms. There is no advantage to saving on your airfare and then wasting precious time in Europe looking for a place to stay.

thank you all for your feedback. I have RS Guidebook and I was going to check his hotel recommendations so when we get there we have an idea of where to stay. I agree with you guys now, I don't want to be stuck with the LEFT OVERS!
Thank you again.

As your research continues, you'll probably feel pretty invested in your plan, and start booking the pieces that most interest you. There's little financial risk to booking ahead, since hotel reservations usually can be cancelled (check how much notice or deposit each one requests). In each of the bigger cities on your list, the major museums also recommend reservations. Next February, you can consider whether you're decided enough to reserve advance-discount train tickets for some longer rides (but no big deal if you're not, as tickets are pretty affordable at regular fare, too).

Consider pushing on to sleep in the Cinque Terre on your first night (and reserve that hotel). If you flight arrives by noon, for instance, and you're at Milano Centrale station by 14:00, there are still several train connections that could get you to the Cinque Terre. If you cut the first night in Milan, then I'd allocate it to Siena.

I'd love to know where your flight is originating and what airlines. I'm also traveling in May 2016 but haven't found anything close to great fares. But maybe we are coming from very different locations??

If you know how long you plan to be somewhere, what's the advantage of not booking ahead? Lots of posters here ask for hotel recommendations because the RS listed hotels are full.

We just returned from 2 weeks in Italy. We booked rooms from airbnb, nearly last minute (10 days before our trip!). They were all wonderful! I picked those with an amazing review record (translation review record), lots of photos, and for us personally... aircondition options, close to areas we wanted and affordable! One family's standard practice is to pick guest up from the bus/train station. That was a bonus in not having to hunt down an address!
The hosts were professional, warm, helpful, and endearing.
Sheila

Nothing to lose and everything to gain from booking ahead, and so easy to do online these days.
Have you considered time (2 nights perhaps) on Lake Como upon arrival, with reduced time in Cinque Terre.
This is a good option to recover from a long flight and ease into things.
This may be simpler ...
2 Nights Lake Como
3 Nights Cinque Terre
3 Nights Rome
3 Nights Florence (with day trip to Siena)
2 Night Milan

I don't see any thing to gain by not having your accommodation done before you arrive.

Two suggestions:
1. Book in advance. With the internet it is quick, easy, and it makes good sense, especially for Le Cinque Terre.
2. Revamp your itinerary; you have too many destinations. Most of what you will see will be through the window of some transport conveyance. The itinerary looks like a marathon at a dead run. Personally, I would drop Siena or add it as a day trip from Florence, drop a day from Le Cinque Terre and add it to Roma.

Where are you flying into and out of?

Buon viaggio,

I'm with the last recommendation to change your itinerary slightly. I love Siena but you would loose more time changing hotels, packing up etc. than by just doing a day trip from Florence to Siena. As nice as Cinque Terre is, I doubt there is twice as much to do as in Florence - quite the opposite is true!

Absolutely book ahead! The best deals are going to be long gone if you wait - and this is ESPECIALLY true of the Cinque Terre: accommodations there tend to fill pretty far in advance, and May is a very busy month there.

As has already been mentioned, arriving in a city and having to run all over - with luggage, and possibly in pouring rain - to hunt down a place to stay is waste of sightseeing time. And if you don't have an idea in advance where you want to to stay, how are you going to know where to start when you get there?

As it is, you're going to lose 1/2 day or more every time you change locations. Add time to find a hotel, and you could easily blow most of a day.

Our flight arrives at 11:00pm that is why we are spending the nigh at Milan first and in the AM we plan to go to Cinque Terre.
The reason we are staying 4 nights at Cinque Terre is to recover from the long flight (19 hours duration) without feeling like we should be out there seeing things ( that is what we would do if we were in Rome, Florence or Milan, we would just kill ourselves).
we have talked about only doing a day trip to Siena and staying one more night in Rome.

airbnb, never used them before but we are definitely interested. I have been looking and adding places we like to our wish list until we can decide in the next few months where we want to stay. :)
thank you everyone for your comments.

I completely agree with the advice to book ahead for all the same reasons. We have traveled in Italy in May a couple of times and it was as crowded as we remembered it in June or July many years ago. According to Wikipedia, Italy logged 44.6 million international tourist arrivals in 2014. In Germany, with "only" 33 million, we thought we could wing it and ended up wasting the better part of a day in Salzburg trying to book a room in Munich (it only takes 1 Optometrist convention) and ended up in Nurnberg for 3 days before finding room at the inn in Munich. Yes, you sacrifice the spontaneity, but with a set itinerary anyway, why worry? And you likely would be distracted from enjoying where you are, thinking about where you are going next, and where you'll stay, etc. I certainly would be. Have a good time!

If you don't like the idea of booking ahead of time (not sure why, but you might have your reasons, maybe can't make up your mind on where you want to go the next day), you can certainly find available rooms in any of the cities you mentioned (except for maybe the Cinque Terre), even the same day, however May is a busy time, therefore you might waste a lot of time doing the search if you rely on walking in and asking if they have vacancies. A more time effective way would be to do a search online the day before or even the same day of arrival, otherwise you will waste the whole morning of arrival looking for a room. Internet searches are quick and more effective. That however would require the availability of a smart phone or at least a wireless connection when you arrive.

Regarding your time allocation, since your flight likely arrives at Milan in the morning or early PM, you could go to the Cinque Terre directly and not waste the first night in Milan.
As I mentioned, the Cinque Terre is a location where you might find more difficulty with accommodations, since they are limited in number, therefore I recommend to book ahead at least the Cinque Terre. Also I think you could cut down the Cinque Terre to no more than 3 nights (that would be 2 full days, which are adequate for the 5 Terre) and allocate those nights somewhere else. Florence certainly deserves at least another night, and probably Rome as well. Siena is an easy day trip from Florence (they are only 40 miles apart), therefore you could visit it from your Florence hotel and save yourself a time wasting hotel transfer.

Another thing you can try is checking booking.com the day before or even the day of arrival, make your reservation, and maintain some flexibility without spending time looking for rooms.

The only lodging I book before I leave is the first one. Then I book the next lodgings when I'm in Italy. I do that because I'm not sure how many days I'll stay in each place. But that takes time away from me. I have to start booking for the next lodging as soon as I arrive at my new lodging.

If you are sure about your itinerary I recommend booking all lodgings before you leave home.

I have a First Cousin from Indiana who met up with me in Firenze in September. Later over dinner at IL Brincello he told me that he and his wife had No reservations when they arrived in Firenze in the late evening. After they got off the train they walked to eight (8) hotels from SMN only to be turned away. The ninth hotel had a room for them.

They too don't have set travel plans. But I can't wing it like he does. He attended college in Europe and is Not phased by having No place to stay even if he arrives in the dark! And his wife goes along with this!

Only he could do that. I could never.

I love not planning everything ahead, and have made half a dozen trips to Italy without reservations. However, everyone of your destinations needs a reservation without question. You can still be casual about hotels for medium and small cities in Italy most times if they are not resorts and not on those stupid bucket lists, but you are visiting tourist epicenters at peak times.

You have allotted almost no time to 'being there' on this trip and a lot of time to checking in and out of hotels and going to and from train stations and just generally getting from one place to another. Given your very little time these places (two nights gives you one full day) to waste another hunk of your time searching for hotels seems unwise. All these places are crowded with tourists and finding a hotel is not always easy. And in my experience at least I get really nice charming hotels when I plan and book and have terrible luck with dumps when I try to do it on the fly.

I would not spend the first night in Milan but go immediately to your first stop e.g. the CT and spend two or three nights there and then head for Florence and spend 4 nights there using one of your 3 full days to do a full day trip to Siena by bus (saving one moving hassle) and then take the train to Rome for 4 nights and return to Milan. You get nothing out of that first night in Milan and adding another one night stand for Siena (which is not well connected to anything by train but particularly not MIlan or Rome) just increases the logistics.