Flexibity arranging lodging for travel throughout Europe in the fall

My husband and I have traveled quite a bit throughout Europe with no reservations. Just know that you can't be picky...you get what's available! The other downside is that finding a place whenever you arrive in a new destination can eat up quite a bit of time. Since you're there for two months though, it shouldn't be a very big deal since you'll be staying in each place for multiple days.
We love the flexibility of staying as long as we like and being able to adjust our plans based on weather, new places we hear about as we go, and plain-old whims!
Often times, tourist offices can be very helpful with this and, depending on where you are, will call around for you to area B&Bs for you to find a spot. This is true usually in smaller places...occasionally in big cities. With the internet you can also make your own reservations the day-of, based on availability.
Know that September is convention season in big cities of Europe and lodging is at a premium...you may want to focus on smaller places at the beginning of your trip and save big cities for October.

How very helpful. Thank you!

Wow, so many places. For a trip of 2 months I'd recommend an average stay of 4 nights at each location, in order to ward off fatigue. That makes 15 destinations and for me would leave no room for either Britain, or Russia (where a visa is required). I'd order my routing like this, and choose hotels with free wifi, booking at least a week in advance. Note that October can be a busy convention month in the big cities.

Milan >> Lake Como >> Lucca >> Orvieto >> Amalfi >> Ravenna >> Vienna >> Rhineland >> Belgium >> Normandy >> Paris >> Provence >> Barcelona >> Granada >> Seville >> fly to Milan

I often make last minute changes and am very often quite successful. I do find I have the most success in smaller towns, especially in Germany and France. I have less success doing last minute in the UK and in Switzerland. Because I have favourite places to stay in Austria and Italy I book ahead there.

I love the flexibility of adjusting my length of stay after I arrive, and the advantages of having solid weather predictions before committing are obvious. On two recent long trips, except for the first and last stops, I made hotel reservations on the fly, most of them 24 to 48 hours in advance but occasionally up to 3 or 4 days ahead.

Doing this, you are not likely to be able to stay in the best-value or most charming lodgings. If you need air conditioning in places where it is not perceived as necessary by the locals (e.g., northern Italy, Germany) you may have to compromise on location, go up a class (and price), or both. If you stumble upon a town or city during a special event, you may find nothing suitable and have to go elsewhere, so research on this point is highly advisable. And be aware that you may not always be able to add a night or two, because the hotel may be booked for those nights. That happened to me once in Rovinj, a popular Istrian coastal town, and I had to change rooms in one Spanish hotel because the upgraded double they originally gave me was needed for the extended night I asked for.

I used venere.com for Italy and booking.com elsewhere and was dependent on Wi-Fi in each hotel to make future reservations. Generally that worked out OK, but occasionally the hotel Wi-Fi was not working or just didn't reach my room. That was very annoying. If you have a data plan on your phone to use as a back-up plan, this will not be a concern for you. When making a long (likely high-cost) reservation, I try to remember to check the hotel web site before using the booking site; sometimes that saves money.

I don't recommend waiting till you arrive to find a place to stay unless you are traveling by car and planning to stay in small towns. Some tourist offices do arrange rooms for walk-in travelers, but in these days of the internet, some do not. And the tourist office is very often located in the tourist district rather than near the train or bus station where you'll arrive (assuming no car). That leaves you with the choice of carrying/rolling all your luggage to the T.O. and from there to the unknown location of the chosen hotel--possibly in the opposite direction--or checking the luggage at the station (if possible) and returning later to fetch it.

To get an idea of how constrained you'll be in your last-minute lodging choices, I recommend going to your chosen booking web site and inputting dates just a few days in the future for each of your known destinations. Use a duration of stay that matches your current thinking. Booking.com, at least, will tell you at the top of the screen how many of the local hotels are available in its database (some others might have rooms if you contacted them directly). This is before you do any filtering by cost, star level, etc., but it will give you an idea of how tight individual cities may be. Then you can add a price filter and see what that does to the availability number. If the number of hotels available plummets to near zero, you know that either your price-point is unrealistic or the city may book up early because demand exceeds supply. You can then consider making your reservation earlier, perhaps making that city your first or last stop. I started my trips in Rome and Madrid, and I ended one of them in Barcelona. Those are the types of places where there's substantial price risk if you wait till the last minute and plan to stay quite awhile.

We are grateful for these valuable tips. As we draft our itinerary, we are considering adding 2 weeks and reconsidering our route, seeking smaller towns and villages along with visits to the theaters in the cities where my grandmother performed on stage as a accompanist for the Wiere Brothers in the 1950's and 60's. Thanks to each of you, we realize while flexibility might sound good, pre-planned arrangements will anchor our experiences and reduce anxieties. Over the course of our life journey, especially the 56 years we have shared life on this magnificent planet, we have accomplished the flexibility to take this adventure. What more can we ask? Again, thanks to all of you for supporting us as we prepare for a magnificent celebration of what is beautiful about humanity.

Even with 2 months to play with, it seems like wa-a-y too many destinations to me. For example, Provence/Paris/north coast France is 3, not 1. Similarly, all your Italian stops are different destinations, which will entail check-in, check-out and travel between - - time and energy consuming. A modest suggestion is that you look into open-jaw routing. Group all your Italian towns together, and redo your itinerary so as to travel in a straight line, more or less.

The visa process for travel in Russia is quite intensive and time consuming from what I hear.

In general, you can arrange lodging on the fly, as long as you aren't picky. Worst case would be if there is something going on in a particular town and so it is filled up. In that case, you need to be ready to hop on a train or bus or even shell out for a cab if it's late/trains aren't running to get to the next town.

Just to test, I went on booking.com and looked for a room in Barcelona for tomorrow, 4 nights overall. There were plenty of choices in your price range. Next test is a smaller town. I picked Orvieto, and again there are multiple options.

Soooo...my advice for hotels: find websites you like now so you know where to start looking when it's time. I like booking.com because it has plenty of smaller bnbs as well as bigger hotels. Have some sort of internet-connected device because doing it online is much easier than calling around in a foreign language, or in running all over town and asking.

And yes, you have too many destinations. Most of the things you list are actually 2+ different hotels (British Isles? That's very broad and could be 10+ hotel stops).