Have you waited till you travel to "book the next segment's hotel?"

We did that, sort of, as a couple. We did Venice Verona Como Florence Assisi Rome.
On arrival, we had Venice and Verona booked. From Venice, we booked Como, from Verona we booked Florence, so stayed two places in front of the pace.
That was in 2006, we are a bit more planned now.

I did that back in the 1990s. After spending days (and nights) and way too much money trying to find a decent place to sleep a few times, no more. As crowded as places have become, I've come to conclude that nailing down all our accommodations long in advance results in greater freedom. While I'm in Europe, I want to be relaxing with a glass of wine, strolling old streets, and enjoying my time there. The last thing I want to do is spend precious hours on my vacation searching for rooms, comparing, checking them out, etc. Some folks are happy "winging it" but I'm done with that.

No one here knows where you are going or the level of travel experience of the person who suggested this. You should let the couple (I assume you you trust them since they are going with you) take the lead in the part of their suggestion; you might learn or experience something better even though you are uncomfortable with it. I do not see what you have to lose. I have found lodging overstock, a lot cheaper the day before versus WAY in advance when there is a lot of stock. The travel industry knows how to cater/ make money off every kind of traveler.

I prefer to wing it, especially when I'm going to an area for the first time, because I'm usually not sure how much time I'll need in each place. However, the lead time for my mid-trip bookings has gradually crept up from about 24 hours to 96 hours before arrival. And I do not push my luck when I'm going to major tourist destinations in periods of high demand.

I spend a lot of time in cities ignored by most American visitors and generally don't have too much trouble finding a place to stay unless I hit a special event. In 2015 I made late bookings in Padua, Orvieto (but that was in May), Lecce (Puglia), and all over Sicily. I was also OK in Bressanone and Bolzano in the summer, but I may have been lucky there. And Bressanone/Bolzano are not overly blessed with air conditioned hotels; especially on late bookings, one may have to go up a hotel class to get a/c.

Even when rooms are available, there are likely still to be trade-offs for retaining flexibility by not booking far ahead. I often have to choose between a place not as central as I would like and a betterl-located hotel that's more than I want to pay. I end up in a lot of places that have what I call "dorm-room decor". You should assume that the high-value and charming places will be the first to fill up. It's worth it to me, but I have the impression that most others don't agree.

Keep in mind that if you are traveling by train, there are often substantial savings to be had by buying non-refundable tickets well in advance. If you're going to do that, you don't have much flexibility about which town you'll be sleeping in each night. So you should really add the extra cost of last-minute train tickets to the hotel-rate penalty you will often encounter when you book late. However, rail fares are not time-sensitive if you are taking short hops on regional trains.

I've done it travelling solo, but I've also done trips with all places planned in advance -- which I do depends on where and when I'm travelling, and what type of crowds I can expect (i.e. will options I like still be available). For my recent trip to Italy, I had all the places planned out because I was staying in VRBO apartments (because I was staying 5 or 6 nights in each city), and those options are much more limited than acceptable hotel rooms; also, I was travelling between cities by train, and I could save several hundred dollars by booking my train tickets in advance. However, I did a 2.5 week road trip in Portugal, and only the VRBO cabin I booked for part of my stay (and my first night's hotel room) were booked in advance.....everything else I booked online from Portugal the day or two before.

Different strategies for different types of trips.

We did that on one trip with some near, as in no place to stay, disasters. Always book hotels ahead. Sometimes we change reservations as we travel .

I have done it before in Italy, France, and Ireland when travel for me was much more spontaneous, waiting to see where the day's travels would take us. But now, as I get older, and as the crowds of tourists increase, (and don't underestimate the crowds of tourists on your trip, Italy will be crowded in May/June) I plan it all out and have accommodations arranged in advance. If I were to go without specific reservations, I would do my research in advance and have lists of possible B&Bs/hotels for the areas I am interested in visiting. Booking at last minute may not get you a place in the price range you are seeking nor with the amenities you may want such as AC, breakfast, fewer steps, etc. Those are all things I look for when researching and by booking in advance I can assure I get what I consider important at a price I think is budget friendly. Also, if you wait you have to take time out of your day to then search (probably via internet) for a place to stay. In the old days we used to go to the local TI and see what they could recommend. Will you be travelling by car? That gives you the freedom to go where you want when you want but if you plan to take public transportation then you probably have a general idea of your overnight stops on your journey. Even by car you could pretty much determine in advance your base stops and then be spontaneous in your daytrip explorations, returning to your base that is booked in advance.

Not a problem at all. I do so all the time, and I travel to Italy in July when it’s more crowded.
Just make sure you have internet devices and WiFi connection to do searches on the go.
The only locations where you might have issues finding vacancies is Venice and possibly the Cinque Terre if you need to be in one of the 5 villages (but there will be plenty in nearby towns like Levanto, etc.
Anywhere else you will find places to stay, albeit not necessarily the specific hotels recommended by Rick Steves.

We did that on one trip with some near, as in no place to stay, disasters

But, how many years ago did this happen; was it before the internet and the tablet and smart phone?

That is our standard style -- but we have been doing it for years and haven't slept in the train station yet. And we are not traveling in June, July or August. We absolutely book the last night prior to returning and the first couple of nights at our first stop. After that it is generally one or two days ahead of time using an internet app but have booked as late as the morning to early afternoon of travel. Never had any serious problems with this approach. One of our most dependable apps is Hotel.com.

And sometimes we don't even have reserved airline tickets for the return. On our last trip in September we didn't get our out bound tickets until ten days before departure and didn't book our return tickets until five days before we came home. Would not recommend that for a group but for the two of us it works. The flights are booked that way because we are using miles and want business class. Would not buy airline tickets in that pattern if paying cash.

We (two of us) were in Italy for May of 2017 with all accomodations pre-booked. For us that works because it just lowers the anxiety level. If we find a place we really like, we "assume we will be back."
After spending a whole vacation day looking for a hotel in Sevilla (holiday weekend in 2007.) I became a book-ahead person. Had done a book-for-the-next-night trip back in pre-internet days.

Sounds like you and the other couple need to discuss -- it's clearly not comfortable for you. Have they traveled in that manner before ? Recently ??

Note that there are LOTS of holidays in May which means many Italians traveling and increased demand for lodgings.

Decades ago I traveled with little advance planning of lodging. But now, with the internet and booking services, and me being a less flexible person, I like hotels and inns with 9+ ratings, spacious rooms, great locations, praise-worthy breakfasts, etc. Those go fast. A couple of weeks ago I finished booking all my rooms for a lengthy trip to Italy in April and May 2020 (almost all can be canceled or changed). I’m a happy camper!

It depends on how important the accommodation and its price is for you. The best (nicest and best value for money) places inevitably get booked up first. If you've already decided on dates and flights Ideal is to do your research really well and decide itineraries and days and then book it up, it also means you don't have to spend precious vacation time searching for accommodation.
However we've also travelled booking everything at the last minute (Puglia this fall) and it worked fine, but I wouldn't risk it high season and be careful about last minute Friday and Saturday nights which can be expensive

Have you traveled with these folks before? My principal concern would be a difference in travel style that will carry over from locations/hotel picks to "What shall we do today?" and "Where shall we have dinner?" As noted by several people time = money/location/quality. Are they prepared to pay the extra that will come with getting desired locations since the most economical options go first? Are you?

Who wants to spend precious vacation time on the internet comparing hotels? Not me. I should add that the hotel experience for me is very important. I am not just looking for a clean bed.

I’m fully aware that it can be done but it makes me uncomfortable. I like a nice hotel/apartment with specific amenities, in a good location, for a good price. Last minute I’m sure you can find somewhere, but most of the time it won’t be as good as what you find booking ahead. You may get lucky, or you may end up overpaying for mediocrity. Some people feel the flexibility is worth the risk, and if you have a decent budget and aren’t picky maybe it is.

My concern would be even more for traveling with another couple. That way you need 2 rooms in the same hotel available, not just 1 room.
If you will be sharing 2 bedroom Airbnb type places, that might be easier.

Maybe another way to approach this is to pick places that have nice day trips you can do, so there is flexibility to see more but not have to move and search for another hotel.

Edited to add: I meant this to book places ahead of time, but then you have flexibility to see other places if you want. I'm too much of a planner to not have my hotels/apartments booked in advance! :-)

I'm of the lots-of-daytrips school of thought myself, but keep in mind that if the lodging situation is tight at a particular destination, it can be a lot trickier to find 4 or 5 nights available at the last minute than 2 or 3. It will probably take two late cancellations of the same category of room at the same hotel to produce a 4- or 5-night vacancy in most cities. This is a situation in which life can be tougher for a slow traveler.

I encourage some exploration on booking.com. See what's available for X nights starting tomorrow: How many hotels in your price range have vacancies, and what do rates look like for a quality acceptable to you? Now change the search to future dates that don't involve local holidays. How many hotels have vacancies? Are rates noticeably lower? That will give you some idea of the cost of doing late bookings. The rate difference will expand at busier times of year, naturally.

I would be curious to know if your friends have ever done that in Italy in May/June!

IMHO, that might have been okay in my 20's, when I could treat sleeping in a train station as a lark. But now, not so much.

Never. I like to have a plan.

Thank you. I just read all your comments. Much appreciated.

When I made the post, I figured it didn't matter WHERE we were going but now I realize that Florence may be a pain to get GOOD/nice accommodation at short notice.

My wife and I have been to Italy before and have read and studied on "it".
Our friends just started reading "page 1" of RS book I gave them.

They asked about booking Venice (our first days) and booking Rome (our last days) but leaving the rest for when we're there.

P.S. Someone asked about my background:
I've gone on 3 month-long trips to Europe. 14+ vacations there (from Scotland to Naples and Portugal to Greece)

We used to wing it - my 2nd trip there was backpacking w/o a plan - slept in the Olympic Village at Rome by jumping the fence.
After our Greek trip where we took a boat to Crete - only to have a very hard time getting good accommodation - have I been 100% planned.

As crowded as places have become, I've come to conclude that nailing
down all our accommodations long in advance results in greater
freedom. While I'm in Europe, I want to be relaxing with a glass of
wine, strolling old streets, and enjoying my time there. The last
thing I want to do is spend precious hours on my vacation searching
for rooms, comparing, checking them out, etc. Some folks are happy
"winging it" but I'm done with that.

Amen to that, David/Seattle!

As much as I'd like to do this--let's call it spontaneous travel--I like to have a plan, and a nice pillow to rest my head at night.

Now--I'm a big fan of the 'base', whether it be Rome, Florence, Salerno, Sorrento, wherever. And from there, I try to leave it as blank a canvas as possible, decide on the day of what to do. This last time in Rome, over a week's time we had a 'Skip The Line' thing for St. Peter's scheduled one day, but other than that it was check our travel books & notes in the morning while eating breakfast at our apartment, figuring out what to do, how to get where we wanted to go, and if we could fit a couple things in on the same route.

Then we'd leave, walk to the bus stop, and off we'd go with our weekly bus/Metro pass in tow. Who cares if we'd get lost? We had a good map to get us back to the apartment, and even if our destinations were a bust, it was still better than being home, and the busts usually ended up being a good story anyway.

I'm not entirely opposed to that approach, as flexibility in the schedule is nice.
But, having limited time there, I don't want to spend that time researching and booking hotels.
If it's a trip longer than a couple weeks, why not?

"My wife and I have been to Italy before and have read and studied on "it".
Our friends just started reading "page 1" of RS book I gave them."

Oh gosh, Evan, this made me laugh. I suspect your friends may be laboring under delusions of hearing about people's trips from years ago when you could rock up to any train station Tourist Information booth and get lodging for the night. They may suggest a Eurail Pass next because you know... they had friends back in the 70/80's who spent the summer backpacking around Europe with a student rail pass.

I DO understand many here on the forum travel this way and are comfortable with it but they are often experienced travelers and know what to take chances with and what to book. I'm way too Type A for that kind of travel!

I'd be more concerned about the issue a couple of folks have raised on whether your travel styles will mesh. Personally, I HATE the "sitting around the table in the AM with people saying well, what do you want to do today...I don't know what do you want to do?" Even for myself, traveling solo, I have a plan. No problem changing it - deleting, adding, swapping - but I don't want to have a blank slate at breakfast. I learn something about planning every trip I take.

Personally, I HATE the "sitting around the table in the AM with people
saying well, what do you want to do today...I don't know what do you
want to do?" Even for myself, traveling solo, I have a plan. No
problem changing it - deleting, adding, swapping - but I don't want to
have a blank slate at breakfast. I learn something about planning
every trip I take.

Pam--

If you've done enough research in advance, don't knock it til you've tried it. Especially in the winter--when travel plans can go completely awry because of weather--it's really the only way to fly. Yes--deleting, adding, swapping--all part of the decision-making process, so it ain't exactly a blank slate. Over the course of the year before, I compile an Excel sheet with tabs and links to just about everything possible to do while parked at a base, and have it at the ready.

But you know--and this is why I detest tours--I hate having to do something on a certain day. Maybe I'm tired (hungover?--although in Italy the wine doesn't kick my a** like it does in the States!) or we just want to take it easy that day. Or we saw something while out the day before that we want to investigate instead. So we juggle our plans and prioritize. At least in Rome, plain ol' wandering is better than attractions to me.

On our next trip, we'll be traveling with another couple--our first time not just the 2 of us--so I understand the possible negotiating process that might ensue.

My wife and I were in Provence a month ago.
We spent time determining a good home base, AND had read a lot. Then, each morning, based on the weather and ____ we'd ask "which town do you want to visit today?"
Pretty easy when you've been married 37 years.

The last time we traveled with others (in a significant way), was two years ago, with a son and his wife, in Spain.
The handy thing was, they didn't mind my having chosen lodging for the entire trip (and paying for it).
But each couple went there own way, when it came to just "walking a town."

But in all my travels since my Crete blunder, I've had lodging pre-planned.
I means less time wasted, when there, trying to find a place. ALSO, when I reserve a place, I KNOW where it is and we get there efficiently.

We’ve done it in Ireland, Germany, Scotland, and Spain when we weren’t sure where we’d end up each day. It worked out fine. In Ireland, Germany, and Scotland we found a place to stay when we got into town. In Spain, we made most of the reservations a day ahead of time. The past few trips we had all our reservations before departure.

I like to plan in advance as well. We were in Italy for almost a month this summer in June and July. I am glad we had reservations as we then knew we had a place to sleep with air conditioning and could get good pricing. I have never done it the way your friends suggest in Italy and am not sure I would be comfortable with it. I think you might find the best places you would want to stay are fully booked without having an advanced reservation, especially needing 2 rooms. I would not want to waste valuable vacation time searching out where to stay. Just my two cents.....

Usually book our hotels (all of them) about 3 months out. Occasionally even in that time frame the first three (or more!) choices come back as no availability. Admittedly these are usually Rick's recommended hotels but still, I rarely think I would like to be looking for a room at 3-5 PM in the afternoon. Depending upon your destination, this coupled with the need to have reserved entries to so many places makes "on the fly" travel a little iffy. This might be especially true in the late May/June time you have scheduled. We are planning Italy for late March next year and a couple of Rick's recommended hotels have already reported no vacancy.

I posed this same question many years ago on this forum. I liked the idea of having some freedom. One person’s reply impacted my travel planning from then on: “Sure, go ahead and wait to book until you get there, Joni. That way you’ll be leaving the nicest rooms and best rates to those of us who plan ahead!” Words to live by, unless you are traveling to less popular destinations in the low season. Good luck convincing your friends of this philosophy, however! Have fun and happy travels!

The only time we have done that lately was on the road not at major tourist stops. We had a list of places that would be convenient and then booked as we traveled and were tired of driving.

For major tourist stops you will end up in terrible places trying this if our experience is a guide. I get great places when I plan and at reasonable prices because I have a choice -- last minute we have often had places that were both unpleasant and expensive because the good places were booked. I would never do this for destination locations, only for long hauls between those places.

A couple of years ago we took two days driving from Paris to the Dordogne -- the first night we booked on the fly and had a fairly terrible hotel. The second night I had booked ahead well in advance and we had a beautiful room overlooking the river in a picturesque town with a lovely restaurant. The hotel was fully booked; it would not have been an option last minute.

What you haven't mentioned is how long is your trip. Has the other couple been to Europe? If it is only a couple of weeks, I would suggest planning it all in advance. If it is a month or more than you could do a "on a whim" trip. I personally agree with many here who have said, I don't want to do hotel planning while on my trip. I think it would be especially true with two different couples making suggestions. I feel the hardest part of planning a trip is hotel selection because a good hotel and its location to public transportation is more important to me than anything. I think both couples should sit down and plan what locations are a must see and go from there. Also remember every time you change cities/hotels you will waste a half day at least in getting settled. As some others mentioned, if you know where you want to go you might accomplish with day trips and minimize your hotel changes. Good luck.