Booking accommodations in advance

I am a moderate budget traveler but I really like to stay in nice places. There are lots of modestly-priced nice places in most cities. But finding them requires advance planning and advance planning allows me to actually meet my travel budget. There's nothing pleasant, in my mind, about showing up in a city after a day of travel and having to sort through places that could be spread all over a city, checking reviews, prices and availability. If you know where you're going, I say you'd do better to plan ahead.

Going with the flow is a nice idea, but you are going to Italy at very busy time. If you are committed to a budget I think you will really benefit from advanced booking. Milan is often surprisingly busy and expensive too. When you have 3 or more nights, consider an apartment. You might pay a little more per night, but you can save some $$ by cooking a meal or two.

Cinque Terre is another one that is become quite overrun and hard to book at the last minute - especially if you are on a budget. I think most savvy accoms now advertise online - it's not like in the old Rick Steves video where the little old grandma shows up and will show you her room she has available.

With the ease of using internet to book now, I think it's harder to find places last minute (on a budget). And I think the reason you would find last minute budget accoms is because they are a dive. Certainly bigger places like Rome or Florence you may be OK, but who wants to spend time looking around a city wasting precious sightseeing hours or going to tourist info centers to find somewhere to stay (your husband wants to wait until you arrive in a city). I'd rather book ahead on a site where I could vet the accoms online and at least read reviews so I don't end up in a filthy hovel. (Having flashbacks to a time before internet and we stayed in a motel outside Boston because we were desperate - it was late - and looking for something cheap. The next morning, the desk guy asked why we stayed and told us there was a crack den in the back...NEVER AGAIN!).

You can certainly leave it until a few days before, then use expedia or trip advisor or one of the other booking engines if you aren't sure where you will be on a particular day).

In March of 1989, I arrived in Milan without reservations - and had great difficulty finding a room on my low budget. Now with the Internet making advance booking so much easier, I'd be much more worried. If you hit a convention or trade show (and Milan gets lots of these), the whole city can be booked.

In Florence there was a vacancy - but the hotel only had a triple for my first night, and it cost me extra (they gave a partial reduction). Again, this was in March of 1989; I wouldn't even think of arriving in Florence in May or June of 2017 without reservations.

If you're really price sensitive (and under 75 USD per night is VERY low for Italy), it's much safer to book ahead. Furthermore, how much of your vacation do you want to spend looking for accommodations? And finally, I'm not sure there are so many places in Italy that are not on websites, that are going to be such bargains, and that won't be booked in advance.

There have been several threads on the question of "book ahead or go with the flow?" It does depend on your travel style, your tolerance for risk, your destination, and when you are going there. But these days, Italy's low season gets shorter and shorter every year, and late April to early June certainly isn't it. If you had a generous budget and were willing to splurge when you needed to (because cheaper places were booked), winging it could work. Since you don't want to pay over $100 per night (again, not a huge budget for Italy), you could be in trouble.

The margin for error is especially small for Italy. It's an expensive country for accommodations anyway and you are going to places that are in demand. I'm not sure if this even qualifies as shoulder season, as someone alluded to. (I was there a couple of months ago myself, I managed to average around $85 a night for a single booking just a few days before I left on booking.com. But this was late October/early November and I did not need a double). In your situation you absolutely should book ahead. If it seems arduous to find a hotel now, you probably do not want to spend valuable sightseeing time finding a room. You would probably end up compromising on quality, price, location, or all three. If your like my wife and me, you would also get tired of dragging your bags around in the process and just settle for worse accommodations than you might otherwise have prebooked.

I have often weighed in on this question; and when I started to read Valerie's response, my first thought was that I had already posted my opinion. I'll just say I second hers.

Some folks declare that a room is just a place to sleep, so they only care that it's clean. I have different point of view. We older travelers get worn out by days of sight-seeing. I like to have a pleasant environment for after dinner relaxation. No night life for us. We also tend to do 3+ week trips. Too many nights in cramped and/or unattractive surroundings starts to get me down.
While we have a somewhat larger budget than pekrebs, I wouldn't ever consider $200/night, except, perhaps, in Paris. Obtaining those attractive, reasonably-priced lodgings usually means you need to book ahead.

In 2005 a friend and I spent 3 weeks in France late June through mid-July with only reservations for the first few days and last days.
But we had a rental car. We figured if one town/village was full, we could drive on to the next. We enjoyed the flexibility, especially when I got food poisoning and couldn't leave the hotel room for 36 hours ...
Our fall-back plan was "we can always sleep in the car ...!"
Even then, finding places to stay was challenging and most places were already booked.
As much as I love the idea, I wouldn't do that again.
And as others have said, your budget is very small for lodging. I think you should book everything ahead. (I'll be in Italy this Spring and found inexpensive lodging at convents. Check Monasterystays,com)
If you find that you are in one locale too long, you can do day trips to places nearby.

I find lots of places under $100 in Italy; in Roma, I stay at a family-run hotel for €75/night with breakfast, single, through booking.com.

I traveled through Italy for 2 months in 2015 without reserving in advance except for my initial location (Rome). I didn't usually know where I was going until I bought my train tickets a day or two before departure. Twice (in Sicily, in June) I tried showing up at the tourist office to find a room. It did not work very well, and as already mentioned, I had a choice of either checking my suitcase at the RR station--and trekking back there later to pick it up--or taking it with me on the 1-mile-or-so hike to the T.O. You can no longer count on finding a T.O. right at the train station, and not all T.O.s will book rooms for you. After my Sicilian experiences I booked rooms 1 to 3 days ahead of time via the Internet, using my hotels' Wi-Fi, to avoid wasting precious sightseeing time.

I am a solo traveler, do not mind tiny rooms and tiny showers, and do not care about hotel breakfasts (rarely worth much of anything in budget hotels). Clean, conveniently located and inexpensive are my goals. Two people traveling together probably need a bit more elbow-room, which is not a given in budget-priced European lodgings. If you want to avoid upper floors in buildings without elevators, that's an additional issue, at least in Italy.

Other complications:

By May you may need air conditioning. My experience is that if you're looking for a last-minute room with air conditioning during a hot spell, at least in northern Italy, you may have to compromise on either price or location, and possibly on both. I got pushed up over 65 euros a few times, and once to about 100 euros--and I was not visiting places in the Venice / Florence / Sorrento / Cinque Terre price range. Would you believe Bolzano? (It was a very, very nice hotel, but...)

The more nights you need in a city, the harder it's likely to be to find an acceptable room at the last minute. When this happens to a solo traveler, it's a royal pain; when you are two people traveling together, I think it could cause unpleasantness.

I urge you to book something now (preferably with air conditioning) for your best guess of the dates you'll be in each city. Make sure the reservations can be canceled without charge at least up to 72 hours before arrival, preferably until one day before. (This probably means hotel rooms rather than apartments.) If you foresee a need to reschedule as your trip progresses, adjust those back-up reservations or cancel them and make new ones until you're confident of your arrival date and can make final plans. See how it goes, and please report back to us on where it worked vs. where you had to fall back on the reservations made previously.

The last time we were in Venice (in late September), we met a guy who had arrived without a reservation. He spent hours looking for a room and ended up in what he called a "crappy hotel" for 250 euros a night. That would definitely blow your budget and put a damper on your trip.

Book ahead, using booking.com. Choose places with a 48-hour free cancellation so you still have a little flexibility. (Be careful when booking ... not all hotels offer free cancellation.) And enjoy your trip!

pekrebs, I hate to pile on, but you have gotten excellent advice here. Particularly in high season, planning at least three or four months in advance, will allow you to pick among the most central and highly-reviewed lodging units, ideally within or near your budget. If you are lucky, you might get both a good price and the right to cancel at no cost, but you will often find the right to cancel comes with a price, and "non-refundable" is cheaper. If you wait until you arrive to seek lodging, you may find the choices are absurdly expensive, or crummy places, or not very accessible places, or with shared bathrooms, or one night here, one night there, instead of the same nice room for three nights in a row. If you go to booking.com or a similar site a few days in advance, at least you can input your budget and your dates, and see what is still available at that time, and book something then. But frankly, I'd rather spend my time doing that at home before I travel, and with many wonderful lodging spots still available. I am doing that this week for my own trip in May and June.

"My husband says we can find places that aren't available on websites once we get there."

There are places in Rick's guidebook that aren't bookable online, or only through their own web sites, but the Italy book sells a lot of copies. It's true that you can go into a village in the Cinque Terre and ask locally who has rooms to rent, but that's risky in June and doesn't really apply in the big cities. Italian tourist information offices have rarely been as helpful a resource as in countries further north.

I had a further thought. It sounds as if you are not very experienced with European travel. You may be surprised at accommodations in Europe. Things we Americans take for granted, such as the availability of inexpensive chain motels with modern fittings pretty much don't exist, except on the fringes of cities. Often there are no elevators even in multi-story buildings. As mentioned above, the presence of AC is not a given.

Don't get me wrong, we love Europe. I've lost track of how many times we've been, and we'll continue until we're too feeble to do so. What places may lack in modern conveniences is more than compensated for by charm and individuality. However, it's hard to shed your American assumptions.

I suggest you at least look at booking.com to get a feel for what is available for your dates and at what prices. Understand that "no availability" means they don't have rooms; but the hotel, itself, may still have some. (That message can be a bit panic inducing.). Keep in mind that Italy is one of the world's top travel destinations, and you'll be there in high season.

You don't say how old you are, but let me say that sleeping on a bench in a train station is fun and romantic when you're 20; not so much later. Book the rooms ahead of time. Yes, it cuts down on the spontaneity, but you can still make your own restaurant, museum, and sightseeing discoveries.

On one vacation in Europe we did not make any reservations of hotels before we left except for the first and last nights. It was in October so it was reasonable to expect that hotels would not be fully booked even up until the last moment. Although we made a plan of where we wanted to stay every night we wanted to retain flexibility to extend our stay if we particularly enjoyed one of those locations. It was in the early days of the internet and it was our plan that we would not reserve our next hotel until the night before we wanted to stay there. So maybe it's not quite the flexibility that your husband wants but it is close.

In fact it worked really well although not without some communication problems. We only speak English and so entering into some hotel web sites without "Google translate" often presented a problem. On those occasions, which were plentiful, we would ask our current hotel to make the reservation for us. We never were unable to get a room in our planned hotel - but remember it was the shoulder season and in your case early June is getting dangerously close to high season. Also we were willing to accept a price that was higher than could be achieved by booking well in advance. As it happens we ended up following the plan for every day of that planned vacation and never extended our stay anywhere. Not because we weren't tempted to stay longer in some places. In fact it was more because we did not want to miss any time in the next place on the itinerary.

Add to that, if you go with the flow, you will be paying a lot more for train rides than if you book a couple months in advance (or whenever tickets go on sale). Rome to Naples - buy at full price €44 (fast train 1 hour), buy in advance €25 or even the not-so-fast 2 hour train is €27 on the spot, €10 in advance. Multiply the difference by 2 tickets. If that doesn't convince him, then you may end up in 8-person dorm rooms in a youth hostel to balance the cost.

A compromise would be to reserve a room for your first night(s) and then make reservations a day or two in advance as you go. using your phone or the internet. I have used this method in a limited way, but holiday weekends can still be a problem. I recommend reserving in advance using booking.com or similar and get a deal that can be cancelled up to a few days before the date. That is what I do now. In the last 15 years I have found myself scrambling to find a room several times and ended up in a less-than-desirable situation. The room wasn't as nice as I wanted, or it was more expensive than desired. On booking.com you can filter to look for rooms in your price range. In Paris, for instance, I saw a number of hotels offering rooms for less than $100. These hotels were mostly away from the city center. Some were in Montmartre. Often the neighborhoods are quite safe and interesting. Public transportation in Paris and other cities is usually good. Another choice is to stay in hostels. In Bath, England, the local YMCA has private rooms at very reasonable rates. I've stayed there half a dozen times in the last 18 years. Except on weekends, I have found a bed there at the last minute. Many hostels are open to drop-ins. Of course, if they are full, you're out of luck. In any situation where you expect to find a room after arriving in a new town, arrive in the morning and look for hotels after 10 am. This is what Rick Steves suggests. I've had that work for me, especially in a smaller place like Monterosso in the Cinque Terre. BTW, late April to early June is a moderate to very busy tourist season in much of Europe. It's a nice time to be there.

Just to echo a couple of points above:

If you're really price sensitive (and under 75 USD per night is VERY
low for Italy), it's much safer to book ahead.

In the last 15 years I have found myself scrambling to find a room
several times and ended up in a less-than-desirable situation. The
room wasn't as nice as I wanted, or it was more expensive than
desired.

If you wait until you arrive to seek lodging, you may find the choices
are absurdly expensive, or crummy places, or not very accessible
places, or with shared bathrooms, or one night here, one night there,
instead of the same nice room for three nights in a row.

Desired price is going to be the most compelling reason to book ahead. It is really low for your Italian destinations, and especially low for decent, last-minute rooms. I won't say it's impossible but too much of what may be available for that price 'on the fly' may be only marginally acceptable (or worse).

But these days, Italy's low season gets shorter and shorter every
year, and late April to early June certainly isn't it.

We've been to some of your locations in May and they were plenty busy. I don't know as I'd even call May shoulder season anymore, although it's a great month weather-wise. Yes, it may be hot here and there, and you might want air con if sensitive to heat.

I would definitely pre-book for the Cinque Terre. I remember a number of panicked posts on the forum last winter from people finding a lot of places already booked up for May.

Back in the 80s, when TI offices included room finding services and were located in train stations, it wasn't difficult to "wing it". That seems like a hundred years ago, being handed a slip of paper with a hotel name, address, and price by the TI staffer.

I would never ever never arrive in a city or town without a reservation. You can book online the night before, but for me that's calling it too close. I don't want to spend time on my trip scrambling for a hotel, but it's a personal preference.

If I was in my twenties with a backpack, Rail Pass and a smartphone with T-Mobile....I'd consider it. Tell your husband to get a time machine OR book all your hotels. I think you should have booked rooms three months ago.

Does your husband have any specifics on how you will find places that aren't available on websites once you get there? Are either of you fluent in Italian? Has he done this lately? What is his contingency plan for the nights when you can't afford any of the lodging that is available?

I'm on Team Book Ahead!!!

We never have reservations, except in our arrival and departure cities; however, we also travel by car and take public transportation into the cities that we want to visit. For such a long trip, I am surprised that you haven't looked into leasing a car, which is cheaper than renting. Driving in Europe is very easy, despite what you might read to the contrary and certainly gives you more flexibility.

How much time do you want to "winging it in a city" by walking back and forth through the city dragging your luggage in the heat. It may take hours and hours to find a place and you will probably spend more than if you reserved ahead of time. When traveling, we are limited by two factors, time and money. You are staying a month so you have more time than the normal person, but do you want to spend that time looking up hotels on a phone, when you could have done the same at home before you left?

It does seem like many people my age or younger or a few years older, like "go with the flow", or "spontaneous-ness", this is nonsense, I prefer to always minimize doubt or uncertainty or randomness when I travel. In general I prefer to make my plans in advance.

I would never travel anywhere, not in the USA or Italy or anywhere, without making an advanced reservation for my hotel or other loging place. Everybody else who replied that you should make all of your hotel reservations in advance, is right. You never want to waste time trying to find a place to sleep after your trip has started. Don't risk having to sleep in a train station or airport because you couldn't be bothered to make hotel reservations and every place was full or too far above your budget.

...I will say, tho I love making advance plans...we did (kinda) wing it for one night in California when we went. We had one night where we would be travelling the coast and weren't sure where we'd be (couldn't book weeks ahead). The night before, we looked at a map, said let's stop here, I got on Expedia and booked a room. But we had a vehicle and weren't relying on public transport, so I could be more flexible with where we stopped...if I couldn't find a suitable spot, we could drive a little further or stay a little out of town with no issue.

I have done Europe ad hoc and can tell you that it can be done. But not in the parts of Italy you want to visit at the edge of season for the price you want. My personal preference (esp. for Venice and CT) is to not "book cheap". I book early at better places, get better prices and accommodations by booking direct and have no worries. That is what I call a vacation now. When I was younger and more adventurous I would show up and hope for the best. But I no longer want to stay in hovels or hostels.

I wish you luck on your journey and I hope you have a wonderful time. I also hope you book ahead at least for CT & Venice. Perhaps I'll see you there as we are spending May in the same region.

Kaeleku,
I see your blog is all Eastern Europe, have you traveled in Italy or more "touristy" areas?