We need more hotel options!

You might go to www.tripadvisor.com and get on specific forums for Rome, Florence, and Cinque Terre. There are likely many more hotel choices and recommendations there. Popular places regularly book out up to a year in advance but you might find other choices on Trip Advisor. Good luck.

Have you tried booking.com? Aggregates a huge number of hotels and contains a lot of reviews.

Drew, we use booking.com almost exclusively to choose our hotels and haven't ended up with a bad one yet. Some may have not been wonderful but those tended to be in areas where hotels were few and far between to begin with so choices were limited. But accommodations do start booking up pretty far in advance of high season, and the best go first.

I usually make our bookings 6-9 months out, depending on location/season.

What Kathy said.

Have you checked the websites of the towns/cities you are visiting? They should have hotel info. What site were you using?
Trivago is another website you could check.

Drew,

It would help to have some idea which hotels you've checked, especially in the Cinque Terre. Also, you mentioned that some hotels had only a "couple of rooms". How many rooms do you need?

If you haven't tried already, I would email the hotels directly. We had several instances of hotels showing booked/sold out when searching online, but when we contacted them directly there were still rooms available--and in all cases, we were booking closer in than 4 months. Not sure where you've tried yet, but we've stayed at La Spiaggia twice in Cinque Terre and been very happy with it--not the fanciest, but clean, in a great location, and we find the owner (Andrea) to be quite the character in a good way. We stayed at Hotel Smeraldo in Rome, again not fancy, but in a prime location near Campo di Fiore, and we were able to walk to all the major sites. Room was small but clean--good value for your money.

We've stayed at La Spiaggia as well and made that booking directly with the hotel. Responses to emails are a bit sporadic in the winter when they're closed so be patient. That one doesn't have any problems filling rooms quickly and early so I'd have another couple of choices in your back pocket.

http://www.laspiaggiahotel.com

I believe I remember some January posts by frustrated RS readers having difficulties finding May availabilities in the CT last year; it's a very popular destination. If you really can't find anything suitable in the 5 towns, take a look at Levanto? It's only a few minutes north of Monterosso and very often recommended as a back-up.

Americans take up less than 10% of Italy's hotel nights so I don't think RS should be blamed for filling the whole country. You can see the Cinque Terre and enjoy other Ligurian towns at the same time. Try the aforementioned Levanto or Sestri Levante or Portovenere. This article gives an overview: http://www.apathtolunch.com/2015/10/liguria-hotel-guide-city-selector-Part-1.html

The CT only has 2 rooms left? Sounds like Drew is relying on some obscure hotel booking website that is offering no rooms so therefore the conclusion has been drawn that all of Italy is booked up.

It's best to deal with the hotels directly, Drew, via email or telephoning directly.

Or maybe trying to book strictly at accommodations listed in the RS guidebook?

@Mike, never blamed Rick, not sure how you get that from what I wrote. Actually, I think it's a good thing he has so many loyal followers and the hotels he has in the guidebook fill up very quickly. Additionally, if you read his books you'll see he says in several restaurants and hotels "you'll find a copy of his guidebook on almost every table" or "watch my episode in the lobby of the hotel" implying the loyal following takes his recommendations to heart.

I sent out emails to everyone directly in the guidebook. I almost always book directly with the hotel vs a 3rd party. I try to only stay in Rick Steves recommended hotels, sure there are others in Cinque Terre but if Rick doesn't recommend them, then I typically do not want to stay there. Same does with restaurants.

Thanks to the helpful & collaborative comments.

I've used arbaspaa.com for both our stays in CT. Their selections run the gamut from private rooms to apartments to agriturismos and farm houses and hotels and B&B's. You tell them your dates, prices, where you prefer to stay and they'll send you what is available. They also do excursions (hiking, wine tastings, scenic flights) and have (had at least) a store front in Vernazza.

I also use TripAdvisor. I try to book the highest-rated hotel in my price range closest to my desired location. Then I like to check for those hotels in the RS guides. On our last trip to Paris, Strasbourg, Munich and Vienna, only the Blauer Bock in Munich was mentioned by RS. They were all great hotels.

I never stay in Rick Steves' recommended hotels on purpose, because I find they are usually already booked. There are thousands of hotels that are as good or better than his recommendations - the fact that you are following only his suggestions may be the root of your problem finding rooms.

I use booking.com a lot (typically 20-30 reservations per year), I filter by my preferences, and always find something acceptable.

Have a happy anniversary!

What Zoe said. There are lots of good hotels that don't make it into guidebooks.

We stayed at Hotel Margherita in Monterosso and loved it. I have no idea if it is mentioned in any guide books. I emailed many hotels in Monterosso (after narrowing down my choices based on TA reviews of properties) and they were the first to respond with an available room for a great price. We landed up being put in a room with a great balcony. Very Clean, comfortable, great breakfast and a short walk from the tunnel (about 15 min from the train station and not too hilly). It was also a short walk to Ciak (my favorite meal in Cinque terre) and the beach.
Like others have said, due to the season and the time change give them about a week to respond. Some of my emails received an auto response stating they would not respond for a month or so...when they did finally respond it was "sorry sold out" or I had already secured Hotel Margherita.

http://www.hotelmonterosso.it/

Drew,

"sure there are others in Cinque Terre but if Rick doesn't recommend them, then I typically do not want to stay there."

Don't just limit yourself to "RS approved" hotels in the Cinque Terre. There are many good hotels that aren't listed. Again, it would help to have some idea on which places you've tried, and also your price range and desired comfort level. Send me a PM if you don't wish to post on the forum.