When to make reservations

Some hotels are not yet ready to take reservations for 2025 summer. Email them directly and ask when they will be accepting reservations.
It's also very important to grab hotels with air conditioning.
Book air when the prices are workable for you. Use Google Flights to track prices and set price alerts.
We already have our May 2025 flights. July flights should be posted in about a month, and prices SEEM to get better about 30 days after first being posted, but who knows?
Have a wonderful family trip.

"No availability" may show up just because their online booking calendar doesn't go out that far yet. In this situation, I've had good luck just emailing the hotel directly to ask for a booking. If they don't yet know their summer 2025 rates (which is most likely the case), they'll tell you when you can contact them back again to do the booking. I've gotten some great deals on hotels in Europe by booking months and months in advance. The price goes up as the inventory of rooms goes down. When I book far in advance, I pass on the chance to save a little money with a pay-in-full, non-refundable rate. Too much can happen and I want flexibility.

Agree agree agree with everything that Vickie has just said. Safe travels!

Mathewsln, welcome to the forum.

Do you know which hotels you want to book? It sounds like you have done your research. For July 2025, I'd start checking weekly in August so you can book your rooms as soon as they post. I booked this August's B&B last November when booking opened and both of September's hotels last September. I booked next June's B&B this June. Both B&Bs are very small and the hotels are monasteries. Book direct with the hotels and only book "cancellable" rooms so if something changes you won't be stuck.

I also book refundable flights as soon as the dates open. Refundable not changeable in case I can't travel later. (I'm getting older so life can change quickly.) At this point I have no money invested that can't be recouped. So I wait to buy travel insurance, if I don't have an annual policy, until I start paying for non-refundable tours and tickets.

By then I have my itinerary pretty well planned. I book "A" museums, tours and sights as soon as tickets are available so I'm not disappointed if it's filled. If I don't care about "B" or "C" sights, I'll wait to book.

Have a great trip!

Excellent advice from everyone, I'll just add to check to see if your hotels under consideration have pages on Social Media or if you can sign up for a "newsletter". The hotels I use most often in Paris sometimes will email out a discount code sometimes so might as well see if that works for your Italian hotels.

Agree wholeheartedly with the AC recommendation. I'm guessing you have to work in a vacation around school year commitments.

I always book as early as possible, because we like specific rooms, generally larger and with a view.

If the rooms are not available on their website, I email the hotel. Sometimes they will take reservations and sometimes give me the date when they become available.

I currently have hotels booked for a trip to Italy and Switzerland this September/October, all of which were booked last November, as well as hotels for Greece next October 2025.

All of these are fully cancellable.

Book your hotels when you know when you are going. Book refundable rooms. This way, you can cancel with no penalty since they haven't charged anything. You are going at a very busy time so I wouldn't try to do this too late. Again, you can always make changes assuming they have the availability.

Booking a non-refundable room is like playing craps in Vegas--you're shooting the dice hoping nothing happens between now and then.

As for airfare, even if you buy non-refundable airfare, most airlines will let you change your dates without penatly. (This usually does not apply to the cheapest fares.) And if you have to cancel, they will give you credit towards future flights.

Read the cancellation rules for any hotel carefully. Don't assume you can cancel with no penalty even if it says refundable.

And by all means, in July, you need airconditioning. Don't assume the hotel has it. Make sure you see it in print. (And regardless of what anyone says, you will need it.)

I will also echo the advice given by the others. Email the hotel directly if those far out dates show up as unavailable. Also it is important to NOT book the non-refundable cheaper rate. Plans may change, unforeseen things may happen that necessitate a change in itinerary and the cancellable rate gives you that extra cushion for change or cancellation. I also book directly with the hotel not a booking site, but I carefully read the reviews on tripadvisor and booking.com and look at the photos posted by travellers in addition to those advertised by the hotel. And yes, there are fewer rooms that can accommodate four people, I think you are correct in researching and reserving those family rooms early.

We're doing Florence/Rome/Salerno/Taormina by train in April 2025. Will be booking the air on Lufthansa (Boston/Munich/Florence; Catania/Munich/Boston) within the month, a little early maybe to get maximum discount but I want choices of upgrades, be it the 2-seat rows on the Airbus 330s or the availability of the premium extra-room rows. Hotels or AirBnB's anytime in the next 2-3 months when my traveling companions can agree. Train--Florence/Rome, Rome/Salerno, Salerno/Taormina as soon as they become available in October on Trenitalia, which is 6 months out.

I'll have to research on the Man in Seat 61 site to see how anal-retentive I want to be about my train tickets. In 2017, when checking tickets the trainmen would look at our phones to verify, but I 'think' that was before the QR code. I had hard copies of everything then, and I probably will have hard copies of everything this time as well.

And...I'll secure some type of trip insurance--in 2017, $5000 of 'good-enough' coverage cost around $150. Let's see how that game has changed since Covid.