Hotel Reservation for 2 week trip to Italy in Sept. 2019

I would certainly book for CT and Sorrento at the very least. If you know where you are going--fairly popular places--then why not have it taken care of?

That all depends on how flexible you are. Reservations give you rooms that you want, not the upstairs in the back non-air conditioned single with the rollaway cot in a 1 star hotel by the railroad station. Sorrento is jam packed during the time you are traveling, as are many of the sites you want to visit. Bite the bullet. Get the rooms booked.

I agree that you should book at least Cinque Terre and Sorrento. You may be okay in booking Florence on the fly, you just are likely to have fewer options or you may not get one of your preferred hotels if they are full.

OK, that is what I was thinking. As much as I hate doing all that booking ahead of time I should do it. The follow-up question is we will be using trains and buses for travel, and do I need to also book that ahead of time? Thanks for the responses.

Any time you're on a Freccia or other express train you can save quite a bit of money by buying non-refundable/non-changeable tickets well ahead of time (up until others have snapped them all up). So Rome to Florence could be an early purchase. So could the Freccia or Intercity part of the trips from Cinque Terre to Naples or points south (much will be on a fast train) and from Florence to Cinque Terre (not as much on a fast train).

Take a look at your travel legs on the Trenitalia website. Use these destinations and a date in the near future (September 2019 will not be available for a long time):

Roma Termini
Firenze S. M. Novella
Monterosso (random choice from among the Cinque Terre towns)
Napoli Central (substitute your final train destination between Napoli and Sorrento)

You'll see that the various departures have different mixes of train types. I concentrate on total travel time, the number of transfers required and convenience of the departure time. I also look at the time allowed to change trains, since I don't want it to be incredibly short when I have a suitcase to move around.

Clicking on the little "i" in a circle beside a train number will show you some details. If you see "prenotabile" near the upper left, it means it's a reserved train. Those are the ones whose fares vary, typically rising quite a bit as you get closer to your travel date. But you have to be sure about your preferred date and time before buying your tickets, since the cheap Freccia and Intercity tickets are not changeable or refundable.

There's a second major rail company in Italy, Italo, that runs between the major cities. It would be an option for you between Rome and Florence.

Do not use RailEurope to price out tickets or to buy them. Buy from Trenitalia or, if you have difficulty with that website, try trainline.eu or loco2.com. I believe at least one of those handles Italian tickets.

There's usually no rush on bus tickets. You definitely don't need to think about those before next August. I usually buy mine on the day of travel, but on rare occasions I haven't been able to get on the bus I wanted.

Depending on how adventurous you are you can always find a hotel. The information centers in each city are great resources and can always find you a place. In my experience I book the first and last night of my trip and then "wing it" this is part of the fun and adventure of travel. I never focus on the hotel as the amount of time I am in it is minimal as I want to see "everything". Utilize the city info centers - they are terrific and will assist in any budget and at no charge. They provide directions, suggestions and a vast of other services for their areas and all are trained to assist tourists.

If you book ahead, YOU get to choose where you stay. If you 'wing it' you get what's left. Your choice of how you like to travel.

Given your geographically spread out destinations and time limits, definitely look at flying into Florence and out of Naples ( or the reverse) rather than in/out of Rome which necessitates a lot of backtracking. A 'one way' trip maximizes your time there and minimizes your travel.
The airfare may be a bit more, but do not forget to factor in all the ground transit costs, both the tickets and your time.

After doing it both ways many times, I've come to accept this paradox:

Booking all your accommodations in advance locks you in to a rigid plan, but that gives you more freedom to do what you want.

Seems contradictory, until you realize that 1) you are going to need to sleep somewhere; 2) you are going to spend some time finding and confirming where that will be. You can choose to spend that time in advance of your trip (and produce far better results) or you can spend time while you're on your trip, searching and weighing options before settling (usually for something either expensive or decidedly lacking in amenities and/or charm). IME the longer you wait to determine where you'll sleep, the harder the choice becomes to accept, the less happy you will be with the outcome, and the more you will pay. Do your research long in advance (like, a year ahead or more, for popular places) get the details nailed down, and you end up with a place to stay that's a part of your wonderful travel memories, and you free up your time for relaxing experiences in your destination.

There's nothing that'll bum you out more than searching endlessly into the night for a place to sleep in a popular destination - you end up paying unbelievably high prices for a substandard room just to be done with the search. It's a rotten way to end your day.

FWIW I'm booking things for a trip in summer of 2019 and already finding too many places "sorry, we're full." It's later than you think.

Absolutely not on the trains for a seat. However, advance reservation would allow you to take advantage of any discounts that might be available. But discount tickets come with restrictions relative to changing.

Two weeks, and you include too many places. I would eliminate Cinque Terre for this trip.

If you're nervous about arriving in a city with no place to stay, you can find a place that looks "acceptable" and has free cancellation -- so you can tweak your plans a few days in advance in case you find someplace that looks better. I once booked about a month of hotels in a multi-hour booking.com marathon, and changed one or two.

All good suggestions. I love this forum. I do think we may have too many places planned and are thinking of dropping Cinque Terre and I like the idea of getting reservations that can be changed or cancelled. Thanks everyone!

The information centers in each city are great resources and can
always find you a place.

The Tourist Info Center website for Sorrento states this:

"Sorrento-Sant’Agnello Official Tourist Board is not authorized to make any reservation or to provide particular information concerning accommodation. We advise you to deal directly with the hotels to confirm the price and stay."

So no, I wouldn't rely on Tourist Info desks to obtain accommodations. As mentioned previously, all of the locations on your list will be very, very busy in Sept: I personally wouldn't wait to make reservations if price, quality and location are important to you as much will book up well in advance.

These days (as opposed to 20 years ago) I would not count on tourist information offices to find hotels for me unless that service was announced on their websites. Some even have a policy of not making recommendations.

My wife and I are travelling through Italy for 16 nights in Sept 2019 and we already have six hotel bookings covering our nights using two of the major internet sites e,g. Booking.com, Expedia. Each of our bookings are fully cancellable up to single digit days before arrival which gives us some flexibility to adjust our itenerary before we leave the USA, or to a lesser degree after arrival in country. If you are so bold and willing to lock into your iten you can save 10-20% by purchasing non-refundable rooms in advance, we are not. Or, if you are a marriott rewards or Hilton honors member you can check their offerings in the larger cities. Also, there is a chain called NH Hotels very big in Europe which you can register for their club for free and book direct if it fits the bill. Happy Hunting!

Just agreeing with the others. September in the places you are visiting is high season, and Italy is more and more visited every year, and the specific spots you mentioned are some of the most popular places in the country. Unless you want to spend all your time finding places, and take the risk of paying much more than you want or getting much less than you want, book ahead.

In particular, people have posted that the Cinque Terre, with its combination of very small towns and many many many visitors, can be very hard to find accommodation even far in advance.

I also agree that if you can, you'll do better to try to fly into Florence and out of Naples. If you can't, don't forget to add travel time to and from Rome to your itinerary, and you will definitely want to be near the Rome airport your last night. If you're flying out of Naples, you will need to be near the Naples airport your last night, or else book an expensive transfer from Sorrento, unless you can snag a later flight from Naples. You don't say where you live, but for many US destinations, flights out of Naples that connect to flights to the US can leave very early. For later flights, there's a Curreri bus that runs from Sorrento right to the Naples airport.